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Themed collection Synthetic methodology in OBC

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Review Article

C(sp2)–H functionalization of aldehyde-derived hydrazones via a radical process

This review is focused on the recent advances in the C(sp2)–H functionalization of aldehyde-derived hydrazones via a radical process. Diverse substituted hydrazones including N-heterocycles are afforded under mild conditions with excellent selectivities. In general, an aminyl radical as the key intermediate is involved during the reaction process.

Graphical abstract: C(sp2)–H functionalization of aldehyde-derived hydrazones via a radical process
From the themed collection: Synthetic methodology in OBC
Review Article

Synthesis of polyheterocycles via multicomponent reactions

Polyheterocycles are one of the most desired synthetic targets due to their numerous and valuable applications in various fields.

Graphical abstract: Synthesis of polyheterocycles via multicomponent reactions
From the themed collection: Synthetic methodology in OBC
Review Article

Nitrilium ions – synthesis and applications

Access to both stable and transient nitrilium ions and the use of these synthons in the organic synthesis of imines and a large spectrum of heterocycles and transition metal complexes are succinctly summarized.

Graphical abstract: Nitrilium ions – synthesis and applications
From the themed collection: Synthetic methodology in OBC
Communication

Tandem radical cyclization for the construction of 1-difluoroalkylated isoquinolines via Cu catalyzed and visible light-promoted pathways

A Cu/B2pin2 system promoted cyclization for the synthesis of 1-difluoroalkylated isoquinolines with vinyl isocyanides and bromodifluoroacetic derivatives in moderate to good yields was reported.

Graphical abstract: Tandem radical cyclization for the construction of 1-difluoroalkylated isoquinolines via Cu catalyzed and visible light-promoted pathways
From the themed collection: Synthetic methodology in OBC
Communication

Nucleophilic trifluoromethylthiolation of bromoalkynones with AgSCF3: C(sp)–SCF3 bond formation towards ynonyl trifluoromethyl sulfides

C(sp)–SCF3 bond formation via the AgSCF3 mediated nucleophilic trifluoromethylthiolation of bromoalkynones, delivering various ynonyl trifluoromethyl sulfides in high yields.

Graphical abstract: Nucleophilic trifluoromethylthiolation of bromoalkynones with AgSCF3: C(sp)–SCF3 bond formation towards ynonyl trifluoromethyl sulfides
From the themed collection: Synthetic methodology in OBC
Communication

KI-catalyzed C–S bond formation via an oxidation relay strategy: efficient access to various α-thio-β-dicarbonyl compounds

An efficient and practical methodology to obtain α-thio-β-dicarbonyl compounds was presented under alkaline conditions via potassium iodide (KI) catalysis.

Graphical abstract: KI-catalyzed C–S bond formation via an oxidation relay strategy: efficient access to various α-thio-β-dicarbonyl compounds
From the themed collection: Synthetic methodology in OBC
Communication

Site-specific hydroxyalkylation of chromones via alcohol mediated Minisci-type radical conjugate addition

From the themed collection: Synthetic methodology in OBC
Communication

Palladium-catalyzed synthesis of quinolin-2(1H)-ones: the unexpected reactivity of azodicarboxylate

A Pd(II)-catalyzed synthesis of quinolin-2(1H)-ones from quinoline N-oxides with azodicarboxylates as the activating agent has been developed.

Graphical abstract: Palladium-catalyzed synthesis of quinolin-2(1H)-ones: the unexpected reactivity of azodicarboxylate
From the themed collection: Synthetic methodology in OBC
Communication

Access to 2-Substitued-2H-Indazoles via Copper-Catalyzed Regioselective Cross-Coupling Reaction

From the themed collection: Synthetic methodology in OBC
Communication

Electrophilic fluorination of stereodefined disubstituted silyl ketene hemiaminals en route to tertiary α-fluorinated carbonyl derivatives

A highly diastereoselective synthesis of tertiary α-fluoro carbonyl compounds is reported in only two chemical steps from a simple alkyne through the reaction of stereodefined fully substituted silyl ketene hemiaminal derivatives with Selectfluor.

Graphical abstract: Electrophilic fluorination of stereodefined disubstituted silyl ketene hemiaminals en route to tertiary α-fluorinated carbonyl derivatives
From the themed collection: Synthetic methodology in OBC
Communication

B(C6F5)3-catalyzed transfer hydrogenations of imines with Hantzsch esters

Transfer hydrogenations of imines with Hantzsch esters were realized using 0.1 mol% of B(C6F5)3, and up to 38% ee was obtained for asymmetric reactions.

Graphical abstract: B(C6F5)3-catalyzed transfer hydrogenations of imines with Hantzsch esters
From the themed collection: Synthetic methodology in OBC
Communication

Rose Bengal catalysed photo-induced selenylation of indoles, imidazoles and arenes: a metal free approach

A photo-induced, metal-free strategy was used for the direct C(sp2)–H bond selenylation of indoles, imidazoles and arenes using Rose Bengal as a photocatalyst.

Graphical abstract: Rose Bengal catalysed photo-induced selenylation of indoles, imidazoles and arenes: a metal free approach
From the themed collection: Synthetic methodology in OBC
Communication

Synthesis of spiro-4H-pyrazole-oxindoles and fused 1H-pyrazoles via divergent, thermally induced tandem cyclization/migration of alkyne-tethered diazo compounds

A thermally induced, substrate-dependent divergent outcome of alkynyl diazoamides for the synthesis of spiro-4H-pyrazoles and fused 1H-pyrazoles has been developed.

Graphical abstract: Synthesis of spiro-4H-pyrazole-oxindoles and fused 1H-pyrazoles via divergent, thermally induced tandem cyclization/migration of alkyne-tethered diazo compounds
From the themed collection: Synthetic methodology in OBC
Communication

Exploring bis-(amino)cyclopropenylidene as a non-covalent Brønsted base catalyst in conjugate addition reactions

The catalytic application of bis-(amino)cyclopropenylidene, as a non-covalent Brønsted base, in the 1,4- and 1,6-conjugate addition of carbon nucleophiles to enones and p-quinone methides, respectively, is described.

Graphical abstract: Exploring bis-(amino)cyclopropenylidene as a non-covalent Brønsted base catalyst in conjugate addition reactions
From the themed collection: Synthetic methodology in OBC
Communication

A Brønsted acid-promoted asymmetric intramolecular allylic amination of alcohols

An asymmetric intramolecular allylic amination reaction catalyzed by a chiral Brønsted acid is disclosed, affording biologically intriguing chiral 2-substituted hydroquinolines in up to 90% yield and with up to 93% ee.

Graphical abstract: A Brønsted acid-promoted asymmetric intramolecular allylic amination of alcohols
From the themed collection: Synthetic methodology in OBC
Communication

Palladium-catalyzed synthesis of fluoreones from bis(2-bromophenyl)methanols

Palladium plays a dual role in synthesizing fluorenones from bis(2-bromophenyl)methanols.

Graphical abstract: Palladium-catalyzed synthesis of fluoreones from bis(2-bromophenyl)methanols
From the themed collection: Synthetic methodology in OBC
Communication

Concise total synthesis of (+)-asperazine A and (+)-pestalazine B

The highly convergent total synthesis of dimeric diketopiperazine alkaloids (+)-asperazine A and (+)-pestalazine B is described.

Graphical abstract: Concise total synthesis of (+)-asperazine A and (+)-pestalazine B
From the themed collection: Synthetic methodology in OBC
Communication

Pyrazole synthesis via a cascade Sonogashira coupling/cyclization of N-propargyl sulfonylhydrazones

An efficient approach for the preparation of pyrazoles via a Pd(II)/Cu(I)-catalyzed Sonogashira coupling/cyclization of N-propargyl sulfonylhydrazones has been established.

Graphical abstract: Pyrazole synthesis via a cascade Sonogashira coupling/cyclization of N-propargyl sulfonylhydrazones
From the themed collection: Synthetic methodology in OBC
Communication

Highly efficient asymmetric construction of novel indolines and tetrahydroquinoline derivatives via aza-Barbier/C–N coupling reaction

An efficient approach towards stereoselective synthesis of chiral indolines and tetrahydroquinolines via Zn-mediated allylation of chiral-N-tert-butanesulfinyl imines and intramolecular C–N cross-coupling is described.

Graphical abstract: Highly efficient asymmetric construction of novel indolines and tetrahydroquinoline derivatives via aza-Barbier/C–N coupling reaction
From the themed collection: Synthetic methodology in OBC
Communication

Pd-Catalyzed C–H aziridination of 3,3,5,5-tetrasubstituted piperazin-2-ones

Pd-Catalysed C–H aziridination of 3,3,5,5-tetrasubsituted piperazin-2-ones catalysed by succinic acid. The mechanistic role of the acid is investigated through kinetics experiments.

Graphical abstract: Pd-Catalyzed C–H aziridination of 3,3,5,5-tetrasubstituted piperazin-2-ones
From the themed collection: Synthetic methodology in OBC
Communication

A novel approach to 5H-pyrazino[2,3-b]indoles via annulation of 3-diazoindolin-2-imines with 2H-azirines or 5-alkoxyisoxazoles under Rh(II) catalysis

The first example of rhodium carbenoid-mediated intermolecular annulation of cyclic diazo compounds with azirines and alkoxyisoxazoles is presented.

Graphical abstract: A novel approach to 5H-pyrazino[2,3-b]indoles via annulation of 3-diazoindolin-2-imines with 2H-azirines or 5-alkoxyisoxazoles under Rh(ii) catalysis
From the themed collection: Synthetic methodology in OBC
Communication

Metal-free electrophilic phosphination of electron-rich arenes, arenols and aromatic thiols with diarylphosphine oxides

A metal-free and mild route to aromatic organophosphorus compounds from stable phosphines.

Graphical abstract: Metal-free electrophilic phosphination of electron-rich arenes, arenols and aromatic thiols with diarylphosphine oxides
From the themed collection: Synthetic methodology in OBC
Open Access Communication

Hydrogen-free reductive amination using iron pentacarbonyl as a reducing agent

The concept of hydrogen-free reductive amination can be expanded to metal carbonyls as reducing agents, which can lead to more selective approaches in organic synthesis. The synthetic value of the developed methodology was demonstrated by efficient preparation of a representative range of amines. The reaction proceeds well even in the case of poorly reactive ketones such as benzophenone.

Graphical abstract: Hydrogen-free reductive amination using iron pentacarbonyl as a reducing agent
From the themed collection: Synthetic methodology in OBC
Communication

Synthesis of α-keto imides through copper-catalyzed oxidation of N-sulfonyl ynamides

A novel copper-catalyzed N-oxide oxidation of N-sulfonyl ynamides has been developed, allowing the facile synthesis of various α-keto imides in generally moderate to good yields.

Graphical abstract: Synthesis of α-keto imides through copper-catalyzed oxidation of N-sulfonyl ynamides
From the themed collection: Synthetic methodology in OBC
Communication

Synthesis of cyclopent-2-enones from furans using a nebulizer-based continuous flow photoreactor

Hydroxycyclopent-2-enones and methoxycyclopent-2-enones have been synthesized in a single operation from furans using an innovative continuous flow nebulizer-based photoreactor.

Graphical abstract: Synthesis of cyclopent-2-enones from furans using a nebulizer-based continuous flow photoreactor
From the themed collection: Synthetic methodology in OBC
Communication

A one pot three-component reaction for the preparation of dihydroquinolines with two different ketones and aromatic amines

A three component reaction with two different ketones and aromatic amines was firstly investigated.

Graphical abstract: A one pot three-component reaction for the preparation of dihydroquinolines with two different ketones and aromatic amines
From the themed collection: Synthetic methodology in OBC
Communication

Rhodium-catalyzed benzoisothiazole synthesis by tandem annulation reactions of sulfoximines and activated olefins

Rhodium(III)-catalyzed N-directed ortho C–H activation reactions have been developed for the synthesis of unique heterocyclic benzoisothiazoles.

Graphical abstract: Rhodium-catalyzed benzoisothiazole synthesis by tandem annulation reactions of sulfoximines and activated olefins
From the themed collection: Synthetic methodology in OBC
Communication

Fe-Catalyzed radical-type difunctionalization of styrenes with aliphatic aldehydes and trimethylsilyl azide via a decarbonylative alkylation–azidation cascade

A three-component oxidative decarbonylative alkylation–azidation cascade reaction of styrene derivatives with aliphatic aldehydes and TMSN3 to provide aliphatic azides is developed.

Graphical abstract: Fe-Catalyzed radical-type difunctionalization of styrenes with aliphatic aldehydes and trimethylsilyl azide via a decarbonylative alkylation–azidation cascade
From the themed collection: Synthetic methodology in OBC
Communication

Na2S-mediated synthesis of terminal alkynes from gem-dibromoalkenes

The Na2S-mediated facile synthesis of terminal alkynes from gem-dibromoalkenes, at 20/40 °C under open flask conditions has been developed.

Graphical abstract: Na2S-mediated synthesis of terminal alkynes from gem-dibromoalkenes
From the themed collection: Synthetic methodology in OBC
Communication

Copper-catalyzed highly selective synthesis of 2-benzyl- and 2-benzylidene-substituted benzo[b]thiazinones from 2-iodophenylcinnamamides and potassium sulfide

DBU as a switch could control the selectivity of the formation of 2-benzyl-substituted benzo[b]thiazinones and 2-benzylidenebenzo[b]thiazinones.

Graphical abstract: Copper-catalyzed highly selective synthesis of 2-benzyl- and 2-benzylidene-substituted benzo[b]thiazinones from 2-iodophenylcinnamamides and potassium sulfide
From the themed collection: Synthetic methodology in OBC
Communication

Synthesis of 2,2-bis(pyridin-2-yl amino)cyclobutanols and their conversion into 5-(pyridin-2-ylamino)dihydrofuran-2(3H)-ones

2,2-Bis(pyridin-2-ylamino)cyclobutanols are prepared easily from 2-hydroxycyclobutanone and are transformed into 5-(pyridin-2-ylamino)dihydrofuran-2(3H)-ones via a periodinane-mediated ring expansion.

Graphical abstract: Synthesis of 2,2-bis(pyridin-2-yl amino)cyclobutanols and their conversion into 5-(pyridin-2-ylamino)dihydrofuran-2(3H)-ones
From the themed collection: Synthetic methodology in OBC
Paper

One-pot synthesis of thioesters with sodium thiosulfate as a sulfur surrogate under transition metal-free conditions

We have developed a one-pot reaction to provide thioester derivatives via sodium thiosulfate as a sulfur source under transition metal-free conditions.

Graphical abstract: One-pot synthesis of thioesters with sodium thiosulfate as a sulfur surrogate under transition metal-free conditions
From the themed collection: Synthetic methodology in OBC
Paper

Preparation of acetals from aldehydes and alcohols under basic conditions

A new method for acetalization of aldehydes under basic conditions, which enables protection in the presence of acid-sensitive groups, has been described.

Graphical abstract: Preparation of acetals from aldehydes and alcohols under basic conditions
From the themed collection: Synthetic methodology in OBC
Paper

Rhodium-catalyzed C–H bond activation alkylation and cyclization of 2-arylquinazolin-4-ones

An efficient method for the synthesis of isoquinolino[1,2-b]quinazolin-8-one derivatives and 12-methyl-12H-isoindolo[1,2-b]quinazoline-10-one derivatives is described herein.

Graphical abstract: Rhodium-catalyzed C–H bond activation alkylation and cyclization of 2-arylquinazolin-4-ones
From the themed collection: Synthetic methodology in OBC
Paper

Intramolecular Morita–Baylis–Hillman reaction as a strategy for the construction of tricyclic sesquiterpene cores

The tricyclic cores of quadrane/suberosane and cedrane and related sesquiterpenes were readily available starting from a common intermediate and using an intramolecular Morita–Baylis–Hillman reaction as a key step.

Graphical abstract: Intramolecular Morita–Baylis–Hillman reaction as a strategy for the construction of tricyclic sesquiterpene cores
From the themed collection: Synthetic methodology in OBC
Paper

Construction of bridged cyclic N,O-ketal spirooxindoles through a Michael addition/N,O-ketalization sequence

The first highly diastereoselective TfOH-catalyzed Michael addition/N,O-ketalization sequence of 3-aminooxindoles and ortho-hydroxychalcones was achieved to afford a wide range of bridged cyclic N,O-ketal spirooxindoles in 41–97% yields.

Graphical abstract: Construction of bridged cyclic N,O-ketal spirooxindoles through a Michael addition/N,O-ketalization sequence
From the themed collection: Synthetic methodology in OBC
Paper

Metal-free NaI/TBHP-mediated sulfonylation of thiols with sulfonyl hydrazides

Sulfonylation of thiols has been achieved via NaI/TBHP-mediated cross-coupling of sulfonyl hydrazides with thiols at room temperature.

Graphical abstract: Metal-free NaI/TBHP-mediated sulfonylation of thiols with sulfonyl hydrazides
From the themed collection: Synthetic methodology in OBC
Paper

Synthesis of medium sized aryl-fused nitrogen heterocycles via sequential aryne aza-Claisen rearrangement/Ring-Closing Metathesis

From the themed collection: Synthetic methodology in OBC
Paper

Air promoted annulation of thiophenols with alkynes leading to benzothiophenes

Air promoted intermolecular annulation of thiophenols with alkynes, leading to complex benzothiophenes, is reported.

Graphical abstract: Air promoted annulation of thiophenols with alkynes leading to benzothiophenes
From the themed collection: Synthetic methodology in OBC
Paper

Thermal conversion of primary alcohols to disulfides via xanthate intermediates: an extension to the Chugaev elimination

Heating primary O-alkyl S-difluoro(ethoxycarbonyl)methyl xanthates yields disulfides. This extends to the Chugaev elimination.

Graphical abstract: Thermal conversion of primary alcohols to disulfides via xanthate intermediates: an extension to the Chugaev elimination
From the themed collection: Synthetic methodology in OBC
Paper

A convergent synthesis of vinyloxyimidazopyridine via Cu(I)-catalyzed three-component coupling

The synthesis of vinyloxyimidazopyridine with complete regio- and stereoselectivity has been achieved by the Cu(I)-catalyzed three-component coupling of 2-aminopyridine, 2-oxoaldehyde and alkyne. This protocol is operationally simple and has much potential for the synthesis of heteroarylated vinyl ethers.

Graphical abstract: A convergent synthesis of vinyloxyimidazopyridine via Cu(i)-catalyzed three-component coupling
From the themed collection: Synthetic methodology in OBC
Paper

Synthesis of the 10-oxabicyclo[5.2.1]decane framework present in bioactive natural products

Development of a versatile and scalable synthetic method of the 10-oxabicyclo[5.2.1]decane framework present in bioactive natural products. The evaluation of the anticancer activity of the synthesized compounds against leukaemia showed a promising activity.

Graphical abstract: Synthesis of the 10-oxabicyclo[5.2.1]decane framework present in bioactive natural products
From the themed collection: Synthetic methodology in OBC
Paper

Copper(II)-mediated, carbon degradation-based amidation of phenylacetic acids toward N-substituted benzamides

The carbon degradation-based amidation of phenylacetic acids with aryl amides has been realized in the presence of Cu(OAc)2, which provides a practical route in the synthesis of N-aryl secondary benzamides.

Graphical abstract: Copper(ii)-mediated, carbon degradation-based amidation of phenylacetic acids toward N-substituted benzamides
From the themed collection: Synthetic methodology in OBC
Paper

A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides

A method for the light-driven synthesis of aryl and vinyl alkyl thioethers from a range of C(sp2)–I bonds is reported.

Graphical abstract: A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides
From the themed collection: Synthetic methodology in OBC
Paper

Direct C3-arylations of 2-indolylmethanols with tryptamines and tryptophols via an umpolung strategy

A Brønsted acid-catalyzed direct C3-arylation of 2-indolylmethanols with tryptamines and tryptophols has been established, leading to a series of potentially bioactive 2,3′-biindole derivatives with a broad substrate scope and generally good yields (38 examples, up to 96% yield).

Graphical abstract: Direct C3-arylations of 2-indolylmethanols with tryptamines and tryptophols via an umpolung strategy
From the themed collection: Synthetic methodology in OBC
Paper

Iodine mediated oxidative cross-coupling of unprotected anilines and heteroarylation of benzothiazoles with 2-methylquinoline

Iodine mediated dual C–H activation of Csp3–H of 2-methylquinoline and Csp2–H of anilines for the construction of C–C and C–O bonds and the oxidative insertion of 2-methylquinoline to the benzothiazole under metal and peroxide free condition.

Graphical abstract: Iodine mediated oxidative cross-coupling of unprotected anilines and heteroarylation of benzothiazoles with 2-methylquinoline
From the themed collection: Synthetic methodology in OBC
Paper

Synthesis of unnatural α-amino acid derivatives via selective o-C–H functionalization

Selective o-C–H functionalization of aryl based amino acids including arylation, alkylation, alkynylation, halogenation, alkoxylation, and acyloxylation were developed.

Graphical abstract: Synthesis of unnatural α-amino acid derivatives via selective o-C–H functionalization
From the themed collection: Synthetic methodology in OBC
Paper

Hydrazone–Pd-catalyzed direct intermolecular reaction of o-alkynylphenols with allylic acetates

The hydrazone–palladium catalyzed direct intermolecular reaction of o-alkynylphenols with allylic acetates gave the corresponding 2-substituted-3-allylbenzofuran derivatives at room temperature.

Graphical abstract: Hydrazone–Pd-catalyzed direct intermolecular reaction of o-alkynylphenols with allylic acetates
From the themed collection: Synthetic methodology in OBC
Paper

The cinchona alkaloid squaramide catalyzed asymmetric Pictet–Spengler reaction and related theoretical studies

An asymmetric Pictet–Spengler reaction between tryptamine derivatives and aldehydes has been developed using a cinchona alkaloid squaramide as the catalyst. The reaction produced tetrahedron-β-carbolines in good to excellent yields and ee values. A rational mechanistic pathway was proposed based on DFT calculations.

Graphical abstract: The cinchona alkaloid squaramide catalyzed asymmetric Pictet–Spengler reaction and related theoretical studies
From the themed collection: Synthetic methodology in OBC
Paper

Iodine(III)-mediated intramolecular sulfeno- and selenofunctionalization of β,γ-unsaturated tosyl hydrazones and oximes

A cascade radical cyclization/sulfenylation or selenylation of β,γ-unsaturated hydrazones and oximes was realized under mild conditions with phenyliodine(III) diacetate (PIDA) as the sole oxidant, leading to the construction of diversely functionalized heteroatom-containing pyrazoline and isoxazoline derivatives.

Graphical abstract: Iodine(iii)-mediated intramolecular sulfeno- and selenofunctionalization of β,γ-unsaturated tosyl hydrazones and oximes
From the themed collection: Synthetic methodology in OBC
Paper

Hydroxyl directed C-arylation: synthesis of 3-hydroxyflavones and 2-phenyl-3-hydroxy pyran-4-ones under transition-metal free conditions

Hydroxyl assisted, efficient, transition-metal free and direct C-arylation of 3-hydroxychromone and 5-hydroxy pyran-4-one moieties in the presence of a base, air as an oxidant and arylhydrazines as arylating agents to furnish highly biologically active 3-hydroxyflavones and 2-phenyl-3-hydroxy pyran-4-ones has been developed.

Graphical abstract: Hydroxyl directed C-arylation: synthesis of 3-hydroxyflavones and 2-phenyl-3-hydroxy pyran-4-ones under transition-metal free conditions
From the themed collection: Synthetic methodology in OBC
Paper

DABCO-catalyzed silver-promoted direct thiolation of pyrazolones with diaryl disulfides

Efficient direct thiolation of N-substituted pyrazolones with diaryl disulfides was developed using a combination of DABCO and AgOAc to assist C–S bond formation.

Graphical abstract: DABCO-catalyzed silver-promoted direct thiolation of pyrazolones with diaryl disulfides
From the themed collection: Synthetic methodology in OBC
Paper

Convenient synthesis of 2-amino-3-(arylthio)indoles via the Rh-catalyzed reaction of 3-diazoindol-2-imines with thioesters

2-Amino-3-(arylthio)indoles were conveniently synthesized via the Rh(II)-catalyzed C–S/N–C coupling reaction between 3-diazoindol-2-imines and thioesters.

Graphical abstract: Convenient synthesis of 2-amino-3-(arylthio)indoles via the Rh-catalyzed reaction of 3-diazoindol-2-imines with thioesters
From the themed collection: Synthetic methodology in OBC
Paper

Synthesis of azulene-substituted benzofurans and isocoumarins via intramolecular cyclization of 1-ethynylazulenes, and their structural and optical properties

The preparation of azulene-substituted benzofurans and isocoumarins was established by two types of intramolecular cyclization reaction of 1-ethynylazulenes.

Graphical abstract: Synthesis of azulene-substituted benzofurans and isocoumarins via intramolecular cyclization of 1-ethynylazulenes, and their structural and optical properties
From the themed collection: Synthetic methodology in OBC
Paper

Synthesis of thiazolidine-thiones, imino-thiazolidines and oxazolidines via the base promoted cyclisation of epoxy-sulfonamides and heterocumulenes

Epoxy-sulfonamides react with heterocumulenes (CS2/RNCS/RNCO) in the presence of a base to afford ring expansion products in good to high yields with excellent regioselectivity.

Graphical abstract: Synthesis of thiazolidine-thiones, imino-thiazolidines and oxazolidines via the base promoted cyclisation of epoxy-sulfonamides and heterocumulenes
From the themed collection: Synthetic methodology in OBC
Paper

Synthesis of trifluoroalkyl or difluoroalkyl phenanthridine derivatives via cascade reaction using an intramolecular cyano group as a radical acceptor under photoredox catalysis

In the presence of Ru(phen)3Cl2 or fac-Ir(ppy)3 under visible-light irradiation, the addition of fluorinated radicals to N-arylacrylamides followed by an intramolecular cyano group insertion cascade cyclization process produced the target compounds in moderate to good yields.

Graphical abstract: Synthesis of trifluoroalkyl or difluoroalkyl phenanthridine derivatives via cascade reaction using an intramolecular cyano group as a radical acceptor under photoredox catalysis
From the themed collection: Synthetic methodology in OBC
Open Access Paper

Intramolecular nucleophilic addition of carbanions generated from N-benzylamides to cyclopropenes

An unusual reaction is described, involving a formal intramolecular nucleophilic substitution of bromocyclopropanes with nitrogen ylides generated in situ from N-benzyl carboxamides. This reaction involves cyclopropene intermediates and allows for the facile preparation of 3-azabicyclo[3.1.0]hexan-2-ones.

Graphical abstract: Intramolecular nucleophilic addition of carbanions generated from N-benzylamides to cyclopropenes
From the themed collection: Synthetic methodology in OBC
Paper

Synthesis of spirocyclic orthoesters by ‘anomalous’ rhodium(II)-catalysed intramolecular C–H insertions

Spirocyclic orthoesters are synthesised by ‘anomalous’ Rh(II)-catalysed intramolecular C–H insertion reactions.

Graphical abstract: Synthesis of spirocyclic orthoesters by ‘anomalous’ rhodium(ii)-catalysed intramolecular C–H insertions
From the themed collection: Synthetic methodology in OBC
Paper

I2 catalyzed access of spiro[indoline-3,4′-pyridine] appended amine dyad: new ON–OFF chemosensors for Cu2+ and imaging in living cells

An efficient, easily tuneable route to construct a structurally diverse organic fluorescent probe and its applications towards the colorimetric detection of Cu2+ ions and in vitro fluorescent cell imaging of Cu2+ in HepG2 cells.

Graphical abstract: I2 catalyzed access of spiro[indoline-3,4′-pyridine] appended amine dyad: new ON–OFF chemosensors for Cu2+ and imaging in living cells
From the themed collection: Synthetic methodology in OBC
Paper

Gold promoted arylative cyclization of alkynoic acids with arenediazonium salts

Arylgold(III) species generated from arenediazonium salts and Au(I) under thermal conditions promote the arylative cyclization of alkynoic acids leading to tetrasubstituted lactones.

Graphical abstract: Gold promoted arylative cyclization of alkynoic acids with arenediazonium salts
From the themed collection: Synthetic methodology in OBC
Paper

Scandium as a pre-catalyst for the deoxygenative allylation of benzylic alcohols

Scandium triflate is an effective pre-catalyst for the deoxygenative allylation of benzylic and benzyhydryl alcohols.

Graphical abstract: Scandium as a pre-catalyst for the deoxygenative allylation of benzylic alcohols
From the themed collection: Synthetic methodology in OBC
Paper

Aerobic oxidative acylation of nitroarenes with arylacetic esters under mild conditions: facile access to diarylketones

A regioselective t-BuONa-mediated aerobic oxidative acylation of nitroarenes under mild conditions is developed through a cascade CDC/oxidative decarboxylation process.

Graphical abstract: Aerobic oxidative acylation of nitroarenes with arylacetic esters under mild conditions: facile access to diarylketones
From the themed collection: Synthetic methodology in OBC
Paper

Design and synthesis of a hybrid framework of indanone and chromane: total synthesis of a homoisoflavanoid, brazilane

A chemical backbone of tetracyclic homoisoflavanoid natural products such as brazilin inspired us to design a new chemical scaffold, 6a,11b-dihydroindeno[2,1-c]chromen-7(6H)-one, which is a hybrid structure of indanone and chromane.

Graphical abstract: Design and synthesis of a hybrid framework of indanone and chromane: total synthesis of a homoisoflavanoid, brazilane
From the themed collection: Synthetic methodology in OBC
Paper

Synthesis of polysubstituted pyridines from oxime acetates using NH4I as a dual-function promoter

An NH4I dual-function promoter enables pyridine synthesis through oxime N–O bond reduction and subsequent condensation reactions.

Graphical abstract: Synthesis of polysubstituted pyridines from oxime acetates using NH4I as a dual-function promoter
From the themed collection: Synthetic methodology in OBC
Paper

Synthesis of 2-methylbenzoxazoles directly from N-phenylacetamides catalyzed by palladium acetate

A method to synthesize 2-methylbenzoxazoles directly from N-phenylacetamides catalyzed by Pd(OAc)2 in moderate to excellent yields has been achieved.

Graphical abstract: Synthesis of 2-methylbenzoxazoles directly from N-phenylacetamides catalyzed by palladium acetate
From the themed collection: Synthetic methodology in OBC
Paper

Thermally induced N–S bond insertion reaction of diazo compounds with N-sulfenylsuccinimides: synthesis of sulfides and mechanism studies

A metal-free gem-functionalization reaction of diazo compounds via a formal N–S bond insertion process under mild conditions is presented.

Graphical abstract: Thermally induced N–S bond insertion reaction of diazo compounds with N-sulfenylsuccinimides: synthesis of sulfides and mechanism studies
From the themed collection: Synthetic methodology in OBC
Paper

Axial stereocontrol in tropos dibenz[c,e]azepines: the individual and cooperative effects of alkyl substituents

The conformational (tropos) dynamics of 4,5-dimethyl- and 4,5,7-trimethyl-dibenzazepines 13 and 14 are dominated by strong (≥9 : 1) but opposite axial configurational preferences.

Graphical abstract: Axial stereocontrol in tropos dibenz[c,e]azepines: the individual and cooperative effects of alkyl substituents
From the themed collection: Synthetic methodology in OBC
Paper

A general strategy for the synthesis of indoloquinolizine alkaloids via a cyanide-catalyzed imino-Stetter reaction

A general synthetic strategy applicable to indoloquinolizine alkaloids has been developed using a cyanide-catalyzed imino-Stetter reaction as a key step.

Graphical abstract: A general strategy for the synthesis of indoloquinolizine alkaloids via a cyanide-catalyzed imino-Stetter reaction
From the themed collection: Synthetic methodology in OBC
Paper

Pd-Catalyzed one-pot sequential cross-coupling reactions of tetrabromothiophene

Unsymmetrical one-pot sequential cross-coupling reactions of sterically hindered tetrabromothiophene with arylboronic acid and an alkyne/alkene to afford selective bi-, tri-, and tetrasubstituted aryl/alkynyl-thiophenes with the aid of a palladium catalyst were described.

Graphical abstract: Pd-Catalyzed one-pot sequential cross-coupling reactions of tetrabromothiophene
From the themed collection: Synthetic methodology in OBC
Paper

Synthesis of 4-substituted pyrazole-3,5-diamines via Suzuki–Miyaura coupling and iron-catalyzed reduction

A general and efficient synthesis of 4-substituted-1H-pyrazole-3,5-diamines was developed to access derivatives with an aryl, heteroaryl, or styryl group, which are otherwise relatively difficult to prepare.

Graphical abstract: Synthesis of 4-substituted pyrazole-3,5-diamines via Suzuki–Miyaura coupling and iron-catalyzed reduction
From the themed collection: Synthetic methodology in OBC
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The latest articles published in Organic and Biomolecular Chemistry related to synthetic methodology.

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