A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles

A short and robust approach for the synthesis of 2-(hetero)aryl substituted thieno[2,3-b]indoles from easily available 1-alkylisatins and acetylated (hetero)arenes has been advanced. The two-step procedure includes the “aldol-crotonic” type of condensation of the starting materials, followed by trea...

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Autores principales: Irgashev, Roman A, Karmatsky, Arseny A, Rusinov, Gennady L, Charushin, Valery N
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4505097/
https://www.ncbi.nlm.nih.gov/pubmed/26199654
http://dx.doi.org/10.3762/bjoc.11.112
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author Irgashev, Roman A
Karmatsky, Arseny A
Rusinov, Gennady L
Charushin, Valery N
author_facet Irgashev, Roman A
Karmatsky, Arseny A
Rusinov, Gennady L
Charushin, Valery N
author_sort Irgashev, Roman A
collection PubMed
description A short and robust approach for the synthesis of 2-(hetero)aryl substituted thieno[2,3-b]indoles from easily available 1-alkylisatins and acetylated (hetero)arenes has been advanced. The two-step procedure includes the “aldol-crotonic” type of condensation of the starting materials, followed by treatment of the intermediate 3-(2-oxo-2-(hetero)arylethylidene)indolin-2-ones with Lawesson’s reagent. The latter process involves two sequential reactions, namely reduction of the C=C ethylidene double bond of the intermediate indolin-2-ones followed by the Paal–Knorr cyclization, thus affording tricyclic thieno[2,3-b]indoles.
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spelling pubmed-45050972015-07-21 A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles Irgashev, Roman A Karmatsky, Arseny A Rusinov, Gennady L Charushin, Valery N Beilstein J Org Chem Full Research Paper A short and robust approach for the synthesis of 2-(hetero)aryl substituted thieno[2,3-b]indoles from easily available 1-alkylisatins and acetylated (hetero)arenes has been advanced. The two-step procedure includes the “aldol-crotonic” type of condensation of the starting materials, followed by treatment of the intermediate 3-(2-oxo-2-(hetero)arylethylidene)indolin-2-ones with Lawesson’s reagent. The latter process involves two sequential reactions, namely reduction of the C=C ethylidene double bond of the intermediate indolin-2-ones followed by the Paal–Knorr cyclization, thus affording tricyclic thieno[2,3-b]indoles. Beilstein-Institut 2015-06-11 /pmc/articles/PMC4505097/ /pubmed/26199654 http://dx.doi.org/10.3762/bjoc.11.112 Text en Copyright © 2015, Irgashev et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Irgashev, Roman A
Karmatsky, Arseny A
Rusinov, Gennady L
Charushin, Valery N
A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles
title A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles
title_full A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles
title_fullStr A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles
title_full_unstemmed A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles
title_short A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles
title_sort new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4505097/
https://www.ncbi.nlm.nih.gov/pubmed/26199654
http://dx.doi.org/10.3762/bjoc.11.112
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