Benzannulation strategies for the synthesis of carbazoles, indolocarbazoles, benzocarbazoles, and carbolines

Ankush Banerjee, Samrat Kundu, Arya Bhattacharyya, Samrat Sahu and Modhu Sudan Maji

Org. Chem. Front., 2021, 8, 2710
DOI: 10.1039/D1QO00092F

An integration of condensation/Ullmann-type coupling/bicyclization sequences: copper-catalyzed three-component direct synthesis of [1,2,4]triazolo[1,5-b]isoquinolin-5(1H)-ones

Feng-Cheng Jia, Cheng Xu, Qun Cai and An-Xin Wu

Chem. Commun., 2014, 50, 9914
DOI: 10.1039/C4CC03420A

Recyclization of 2-indolyl cyclopropyl ketones into carbazoles

Konstantin L. Ivanov and Ekaterina M. Budynina

Org. Biomol. Chem., 2026
DOI: 10.1039/D5OB01877C

An organocatalytic highly efficient approach to the direct synthesis of substituted carbazoles in water

Pradeep Kumar Jaiswal, Soumen Biswas, Shivendra Singh and Sampak Samanta

Org. Biomol. Chem., 2013, 11, 8410
DOI: 10.1039/c3ob42034e

Convenient synthesis of benzo[4,5]thiazolo[2,3-c][1,2,4]triazoles with 1 mol% CuCl2·2H2O as catalyst in water

Li-Rong Wen, Shou-Lei Li, Jian Zhang and Ming Li

Green Chem., 2015, 17, 1581
DOI: 10.1039/C4GC02156H

One-pot access to tetrahydrobenzo[c]carbazoles from simple ketones by using O2 as an oxidant

Shuvendu Saha and Modhu Sudan Maji

Org. Biomol. Chem., 2020, 18, 1765
DOI: 10.1039/C9OB02751C

Synthesis of benzo[a]carbazole derivatives from 3-ethylindoles by exploiting the dual character of benzoquinone as an oxidizing agent and dienophile

Chun-Wei Kuo, Ashok Konala, Lyu Lin, Ting-Ta Chiang, Chia-Yu Huang, Tang-Hao Yang, Veerababurao Kavala and Ching-Fa Yao

Chem. Commun., 2016, 52, 7870
DOI: 10.1039/C6CC03124B

Synthesis of dibenzo[a,c]carbazoles from 2-(2-halophenyl)-indoles and iodobenzenes via palladium-catalyzed dual C–H functionalization

Lijun Wu, Guobo Deng and Yun Liang

Org. Biomol. Chem., 2017, 15, 6808
DOI: 10.1039/C7OB01638G

Rhodium(iii)-catalyzed indole-directed carbenoid aryl C–H insertion/cyclization: access to 1,2-benzocarbazoles

Zhenhui Zhang, Kunkun Liu, Xun Chen, Shi-Jian Su, Yuanfu Deng and Wei Zeng

RSC Adv., 2017, 7, 30554
DOI: 10.1039/C7RA04889K

Construction of benzo[a]carbazole derivatives via Diels–Alder reaction of arynes with vinylindoles

Lijun Wu, Hui Huang, Pan Dang, Yun Liang and Shaofeng Pi

RSC Adv., 2015, 5, 64354
DOI: 10.1039/C5RA11025D

Regio-selective synthesis of diversely substituted benzo[a]carbazoles through Rh(iii)-catalyzed annulation of 2-arylindoles with α-diazo carbonyl compounds

Bin Li, Beibei Zhang, Xinying Zhang and Xuesen Fan

Chem. Commun., 2017, 53, 1297
DOI: 10.1039/C6CC08377C

Synthesis of benzo[a]carbazoles and indolo[2,3-a]carbazoles via photoinduced carbene-mediated C–H insertion reaction

Jidong Yang, Qingzhao Zhang, Wei Zhang and Wei Yu

RSC Adv., 2014, 4, 13704
DOI: 10.1039/C4RA00442F

Copper catalyzed oxidative coupling of amines with formamides: a new approach for the synthesis of unsymmetrical urea derivatives

G. Sathish Kumar, R. Arun Kumar, P. Santhosh Kumar, N. Veera Reddy, K. Vijaya Kumar, M. Lakshmi Kantam, S. Prabhakar and K. Rajender Reddy

Chem. Commun., 2013, 49, 6686
DOI: 10.1039/c3cc42381f

Synthesis of benzo[a]carbazoles via cyanide-catalyzed imino-Stetter reaction/Friedel–Crafts reaction sequence

Jiye Jeon and Cheol-Hong Cheon

Org. Chem. Front., 2019, 6, 456
DOI: 10.1039/C8QO01209A

Gold-Catalyzed Direct Assembly of Aryl-Annulated Carbazoles from 2-Alkynyl Arylazides and Alkynes

Nan Li, Xiao-Lei Lian, Yu-Hui Li, Tian-Yi Wang, Zhi-Yong Han, Liming Zhang and Liu-Zhu Gong

Org. Lett., 2016, 18, 4178
DOI: 10.1021/acs.orglett.6b01627

Triggering the Directional Selectivity of a Ring‐Closure Reaction Leads to Pyridoazacarbazoles with Anticancer Properties

Tamara N. Steinhauer, Daniel S. Längle, Christopher Meier, Ulrich Girreser, Lars Stenzel, Dieter Heber and Bernd Clement

Chemistry A European J, 2015, 21, 6668
DOI: 10.1002/chem.201500156

Synthesis of Benzo[a]carbazoles from 2‐Arylindoles via a Sequential Propargylation, Propargyl‐Allenyl Isomerization, and 6π‐Electrocyclization

Jin Woo Lim, Se Hee Kim, Jimin Kim and Jae Nyoung Kim

Bulletin Korean Chem Soc, 2015, 36, 1351
DOI: 10.1002/bkcs.10258

A one-pot direct regioselective iodination of Fischer-Borsche product using periodic acid in PEG-400

Monica H. Ghom, Mahavir S. Naykode, Vivek T. Humne and Pradeep D. Lokhande

Tetrahedron Letters, 2019, 60, 1029
DOI: 10.1016/j.tetlet.2019.03.022

An Efficient, Solvent‐Free and Green One‐Pot Protocol for the Rapid Access to Polyfunctionalized Carbazoles

Anuradha Dagar, Soumen Biswas, Shaikh M.Mobin and Sampak Samanta

ChemistrySelect, 2016, 1, 6362
DOI: 10.1002/slct.201601611

Synthesis of Benzo[4,5]imidazo[1,2-c]pyrimidin-1-amines and Their Analogs via Copper-Catalyzed C–N Coupling and Cyclization

Pham Duy Quang Dao, Ha Kyeong Lee, Ho-Sang Sohn, Nam Sik Yoon and Chan Sik Cho

ACS Omega, 2017, 2, 2953
DOI: 10.1021/acsomega.7b00693

Access to Substituted Carbazoles in Water by a One‐Pot Sequential Reaction of α,β‐Substituted Nitro Olefins with 2‐(3‐Formyl‐1H‐indol‐2‐yl)acetates

Soumen Biswas, Anuradha Dagar, Anvita Srivastava and Sampak Samanta

Eur J Org Chem, 2015, 2015, 4493
DOI: 10.1002/ejoc.201500470

Synthesis of benzo[4,5]imidazo[1,2‐a]indolo[1,2‐c]quinazolines from 2‐(2‐bromoaryl)indoles and 2‐methoxybenzimidazoles under recyclable magnetic MOF‐199 catalysis

Min Jeong Kim, Seong Weon Lee, Pham Duy Quang Dao and Chan Sik Cho

Applied Organom Chemis, 2022, 36
DOI: 10.1002/aoc.6871

Oxidative photochemical cyclization of ethyl 3-(indol-3-yl)-3-oxo-2-phenylpropanoate derivatives: synthesis of benzo[a]carbazoles

Yinlong Li, Zhonghua Pang, Tianqi Zhang, Jidong Yang and Wei Yu

Tetrahedron, 2015, 71, 3351
DOI: 10.1016/j.tet.2015.03.107

A Versatile Pd-Catalyzed Alkyne Annulation Process for Benzo[a]carbazoles and their Anticancer Analogues

Manashi Sarmah, Deep Jyoti Das, Dhiraj Dutta, Rinku Baishya and Pranjal Gogoi

ACS Omega, 2022, 7, 47680
DOI: 10.1021/acsomega.2c04755

Construction of Binuclear Benzimidazole-Fused Quinazolinones and Pyrimidinones Using Aryl Isocyanates as Building Blocks by Transition-Metal-Free C(sp2)–N Coupling

Pham Duy Quang Dao and Chan Sik Cho

J. Org. Chem., 2020, 85, 13354
DOI: 10.1021/acs.joc.0c02067

A Photochemical Route to Benzo[a]carbazoles via Domino Elimination/Electrocyclization of 2‐Aryl‐3‐(1‐tosylalkyl)indoles

Stefano Protti, Alessandro Palmieri, Marino Petrini, Maurizio Fagnoni, Roberto Ballini and Angelo Albini

Adv Synth Catal, 2013, 355, 643
DOI: 10.1002/adsc.201201051

Concise Synthesis of 1‐Naphthols under Mild Conditions through a Copper‐Catalyzed Arylation of Methyl Ketones

Zhenbang Lou, Shu Zhang, Chao Chen, Xinlong Pang, Ming Li and Lirong Wen

Adv Synth Catal, 2014, 356, 153
DOI: 10.1002/adsc.201300728

Facile synthesis of 1-naphthols through a copper-catalyzed arylation of methyl ketones with o-bromoacetophenones

Zhen-Bang Lou, Xin-Long Pang, Chao Chen, Li-Rong Wen and Ming Li

Chinese Chemical Letters, 2015, 26, 1231
DOI: 10.1016/j.cclet.2015.07.022

Synthesis of Functionalized Isoquinolin‐1(2H)‐ones by Copper‐Catalyzed α‐Arylation of Ketones with 2‐Halobenzamides

Yan Shi, Xuebin Zhu, Haibin Mao, Hongwen Hu, Chengjian Zhu and Yixiang Cheng

Chemistry A European J, 2013, 19, 11553
DOI: 10.1002/chem.201301621

An efficient synthesis of 6-hydroxy-6-methyl-5,6-dihydro-8H-isoquinolino[1,2-b]quinazolin-8-ones via a CuI-catalyzed deacylation and no dehydration reaction

Wei-Qing Miao, Jian-Quan Liu and Xiang-Shan Wang

Monatsh Chem, 2019, 150, 1305
DOI: 10.1007/s00706-019-02430-6

Rh(III)-Catalyzed Cascade Annulation/C–H Activation of o-Ethynylanilines with Diazo Compounds: One-Pot Synthesis of Benzo[a]carbazoles via 1,4-Rhodium Migration

Songjin Guo, Kai Yuan, Meng Gu, Aijun Lin and Hequan Yao

Org. Lett., 2016, 18, 5236
DOI: 10.1021/acs.orglett.6b02534

Synthesis of Benzo[a]carbazole Derivatives from β‐(2‐Arylindolyl)nitroalkanes via Mn(OAc)3‐mediated Cyclization

Su Yeon Kim, Jin Woo Lim, Beom Kyu Min and Jae Nyoung Kim

Bulletin Korean Chem Soc, 2016, 37, 1890
DOI: 10.1002/bkcs.10989

Transition Metal‐Free Sulfenylation of C−H Bonds for C−S Bond Formation in Recent Years: Mechanistic Approach and Promising Future

Mohit Saroha, Jayant Sindhu, Sudhir Kumar, Kuldip K. Bhasin, Jitender M. Khurana, Rajender S. Varma and Deepak Tomar

ChemistrySelect, 2021, 6, 13077
DOI: 10.1002/slct.202102042

Metal-Free Double Csp2–H Bond Functionalization: Strategy for Synthesizing Benzo[a]carbazoles from 2-Arylindoles and Acetophenones/Alkynes

Penghui Ni, Jing Tan, Wenqi Zhao, Huawen Huang, Fuhong Xiao and Guo-Jun Deng

Org. Lett., 2019, 21, 3687
DOI: 10.1021/acs.orglett.9b01138

Brönsted acidic ionic liquid catalyzed synthesis of benzo[a]carbazole from renewable acetol and 2-phenylindoles in a biphasic system

Minghao Li, Fengtian Wu and Yanlong Gu

Chinese Journal of Catalysis, 2019, 40, 1135
DOI: 10.1016/S1872-2067(19)63370-X

ChemInform Abstract: Copper‐Catalyzed Synthesis of Benzocarbazoles via α‐C‐Arylation of Ketones.

Ruilong Xie, Yun Ling and Hua Fu

ChemInform, 2013, 44
DOI: 10.1002/chin.201316080

Synthesis of Highly π-Extended Dihydrobenzo[a]indenocarbazole Scaffolds via Tandem Benzannulation and Friedel–Crafts Reaction of 2-Alkynylanilines and 2-Alkynylbenzaldehydes Promoted by Lewis Acid

Archana Chutia, Pallav Jyoti Arandhara and Anil K. Saikia

J. Org. Chem., 2024, 89, 11542
DOI: 10.1021/acs.joc.4c01245

CuI-catalyzed synthesis of (benzo)imidazo[2,1-a]isoquinolinone derivatives via successive α-arylation, deacylation and benzyl automatic oxidation

Wei-Qing Miao, Jian-Quan Liu and Xiang-Shan Wang

Tetrahedron, 2020, 76, 131200
DOI: 10.1016/j.tet.2020.131200

One-Pot Access to Benzo[a]carbazoles via Palladium(II)-Catalyzed Hetero- and Carboannulations

Moumita Jash, Bimolendu Das and Chinmay Chowdhury

J. Org. Chem., 2016, 81, 10987
DOI: 10.1021/acs.joc.6b02022

Selective Synthesis of Benzo[a]Carbazoles and Indolo[2,1‐a]‐Isoquinolines via Rh(III)‐Catalyzed C−H Functionalizations of 2‐Arylindoles with Sulfoxonium Ylides

Guang Chen, Xinying Zhang, Ruixue Jia, Bin Li and Xuesen Fan

Adv Synth Catal, 2018, 360, 3781
DOI: 10.1002/adsc.201800622

Copper Catalyzed C−H Activation

M. Lakshmi Kantam, Chandrakanth Gadipelly, Gunjan Deshmukh, K. Rajender Reddy and Suresh Bhargava

The Chemical Record, 2019, 19, 1302
DOI: 10.1002/tcr.201800107

Access to Benzo[a]carbazoles and Indeno[1,2-c]quinolines by a Gold(I)-Catalyzed Tunable Domino Cyclization of Difunctional 1,2-Diphenylethynes

Xiaoshi Peng, Lifeng Zhu, Yuqian Hou, Yadong Pang, Yangming Li, Jiayue Fu, Lu Yang, Bin Lin, Yongxiang Liu and Maosheng Cheng

Org. Lett., 2017, 19, 3402
DOI: 10.1021/acs.orglett.7b01358

Copper‐catalyzed CN Coupling and Cyclization of 2‐(2‐Bromophenyl)‐1H‐indoles with Primary Amides Leading to Indolo[1,2‐c]quinazolines

Jae Myeong Yoo, Pham Duy Quang Dao and Chan Sik Cho

Bulletin Korean Chem Soc, 2018, 39, 1105
DOI: 10.1002/bkcs.11545

Diazo Compounds: Versatile Synthons for the Synthesis of Nitrogen Heterocycles via Transition Metal‐Catalyzed Cascade C–H Activation/Carbene Insertion/Annulation Reactions

Yunyu Xiang, Cong Wang, Qiuping Ding and Yiyuan Peng

Adv Synth Catal, 2019, 361, 919
DOI: 10.1002/adsc.201800960

Copper‐Catalyzed Synthesis of Trinuclear N‐Fused Hybrid Scaffolds by Double C(sp2)–N Bond Formation between 2‐(2‐Bromoaryl)indoles and 2‐Aminoazoles

Thi Duyen Diep, Pham Duy Quang Dao, Son Long Ho and Chan Sik Cho

Eur J Org Chem, 2020, 2020, 2807
DOI: 10.1002/ejoc.202000238

Copper‐Catalyzed Synthesis of 5‐Arylindolo[1,2‐c]quinazolin‐6(5H)‐ones from 2‐(2‐Bromoaryl)indoles and Aryl Isocyanates under Microwave Irradiation

Pham Duy Quang Dao and Chan Sik Cho

Eur J Org Chem, 2022, 2022
DOI: 10.1002/ejoc.202200479