Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines)

Indol-2-ylmethyl carbanions stabilized by alkoxycarbonyl, cyano or benzenesulfonyl groups react with nitroarenes to form σ(H)-adducts, which in the presence of base (triethylamine or DBU) and trimethylchlorosilane transform into indolo[3,2-b]quinoline derivatives in moderate to good yields.

Detalles Bibliográficos
Autores principales: Nowacki, Michał, Wojciechowski, Krzysztof
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5789443/
https://www.ncbi.nlm.nih.gov/pubmed/29441142
http://dx.doi.org/10.3762/bjoc.14.14
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author Nowacki, Michał
Wojciechowski, Krzysztof
author_facet Nowacki, Michał
Wojciechowski, Krzysztof
author_sort Nowacki, Michał
collection PubMed
description Indol-2-ylmethyl carbanions stabilized by alkoxycarbonyl, cyano or benzenesulfonyl groups react with nitroarenes to form σ(H)-adducts, which in the presence of base (triethylamine or DBU) and trimethylchlorosilane transform into indolo[3,2-b]quinoline derivatives in moderate to good yields.
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spelling pubmed-57894432018-02-13 Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines) Nowacki, Michał Wojciechowski, Krzysztof Beilstein J Org Chem Full Research Paper Indol-2-ylmethyl carbanions stabilized by alkoxycarbonyl, cyano or benzenesulfonyl groups react with nitroarenes to form σ(H)-adducts, which in the presence of base (triethylamine or DBU) and trimethylchlorosilane transform into indolo[3,2-b]quinoline derivatives in moderate to good yields. Beilstein-Institut 2018-01-23 /pmc/articles/PMC5789443/ /pubmed/29441142 http://dx.doi.org/10.3762/bjoc.14.14 Text en Copyright © 2018, Nowacki and Wojciechowski https://creativecommons.org/licenses/by/4.0https://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/4.0), 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
Nowacki, Michał
Wojciechowski, Krzysztof
Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines)
title Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines)
title_full Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines)
title_fullStr Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines)
title_full_unstemmed Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines)
title_short Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines)
title_sort transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. a novel synthesis of indolo[3,2-b]quinolines (quindolines)
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5789443/
https://www.ncbi.nlm.nih.gov/pubmed/29441142
http://dx.doi.org/10.3762/bjoc.14.14
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AT wojciechowskikrzysztof transitionmetalfree33annulationofindol2ylmethylcarbanionstonitroarenesanovelsynthesisofindolo32bquinolinesquindolines

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