Synthesis of benzothiophene and indole derivatives through metal-free propargyl–allene rearrangement and allyl migration

An efficient base-catalyzed protocol for the synthesis of benzothiophene is described. The reaction proceeds via base-promoted propargyl–allenyl rearrangement followed by cyclization and allyl migration. Phosphine-substituted indoles can be synthesized by a similar strategy.

Detalles Bibliográficos
Autores principales: Yao, Jinzhong, Xie, Yajie, Zhang, Lianpeng, Li, Yujin, Zhou, Hongwei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5629416/
https://www.ncbi.nlm.nih.gov/pubmed/29062405
http://dx.doi.org/10.3762/bjoc.13.181
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author Yao, Jinzhong
Xie, Yajie
Zhang, Lianpeng
Li, Yujin
Zhou, Hongwei
author_facet Yao, Jinzhong
Xie, Yajie
Zhang, Lianpeng
Li, Yujin
Zhou, Hongwei
author_sort Yao, Jinzhong
collection PubMed
description An efficient base-catalyzed protocol for the synthesis of benzothiophene is described. The reaction proceeds via base-promoted propargyl–allenyl rearrangement followed by cyclization and allyl migration. Phosphine-substituted indoles can be synthesized by a similar strategy.
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spelling pubmed-56294162017-10-23 Synthesis of benzothiophene and indole derivatives through metal-free propargyl–allene rearrangement and allyl migration Yao, Jinzhong Xie, Yajie Zhang, Lianpeng Li, Yujin Zhou, Hongwei Beilstein J Org Chem Full Research Paper An efficient base-catalyzed protocol for the synthesis of benzothiophene is described. The reaction proceeds via base-promoted propargyl–allenyl rearrangement followed by cyclization and allyl migration. Phosphine-substituted indoles can be synthesized by a similar strategy. Beilstein-Institut 2017-09-06 /pmc/articles/PMC5629416/ /pubmed/29062405 http://dx.doi.org/10.3762/bjoc.13.181 Text en Copyright © 2017, Yao et al. 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
Yao, Jinzhong
Xie, Yajie
Zhang, Lianpeng
Li, Yujin
Zhou, Hongwei
Synthesis of benzothiophene and indole derivatives through metal-free propargyl–allene rearrangement and allyl migration
title Synthesis of benzothiophene and indole derivatives through metal-free propargyl–allene rearrangement and allyl migration
title_full Synthesis of benzothiophene and indole derivatives through metal-free propargyl–allene rearrangement and allyl migration
title_fullStr Synthesis of benzothiophene and indole derivatives through metal-free propargyl–allene rearrangement and allyl migration
title_full_unstemmed Synthesis of benzothiophene and indole derivatives through metal-free propargyl–allene rearrangement and allyl migration
title_short Synthesis of benzothiophene and indole derivatives through metal-free propargyl–allene rearrangement and allyl migration
title_sort synthesis of benzothiophene and indole derivatives through metal-free propargyl–allene rearrangement and allyl migration
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5629416/
https://www.ncbi.nlm.nih.gov/pubmed/29062405
http://dx.doi.org/10.3762/bjoc.13.181
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