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Issue 35, 2016
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Synthesis of decahydropyrrolo[1,2-a]tetrazolo[1,5-d]pyrazines via Strecker reaction and intramolecular [3+2] cycloaddition

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Abstract

This paper reports an efficient two-step method for synthesizing a series of new (5aS,10R)-10-aryl-5,5a,6,7,8,10-hexahydropyrrolo[1,2-a]tetrazolo[1,5-d]pyrazines by a catalyst-free three-component Strecker reaction followed by an intramolecular [3+2] cycloaddition. The first step involved three-component coupling of aldehydes, (S)-2-(azidomethyl)pyrrolidine and potassium cyanide in presence of water to form (R)-2-((S)-2-(azidomethyl)pyrrolidin-1-yl)-2-phenylacetonitriles (3a–3v). In the next step products (3a–3v) underwent intramolecular [3+2] cycloaddition on heating to form (5aS,10R)-10-aryl-5,5a,6,7,8,10-hexahydropyrrolo[1,2-a]tetrazolo[1,5-d]pyrazines (4a–4v). The present methodology is cost-effective, operationally simple, and applicable for various aromatic, aliphatic and heterocyclic aldehydes, and gives desired products in satisfactory yields and diastereoselectivities. A proposed mechanism for synthesis of 3a and 4a is reported.

Graphical abstract: Synthesis of decahydropyrrolo[1,2-a]tetrazolo[1,5-d]pyrazines via Strecker reaction and intramolecular [3+2] cycloaddition

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Article information


Submitted
02 Jan 2016
Accepted
09 Mar 2016
First published
11 Mar 2016

RSC Adv., 2016,6, 29783-29793
Article type
Paper

Synthesis of decahydropyrrolo[1,2-a]tetrazolo[1,5-d]pyrazines via Strecker reaction and intramolecular [3+2] cycloaddition

S. N. Afraj, C. Chen and G. Lee, RSC Adv., 2016, 6, 29783
DOI: 10.1039/C6RA00063K

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