[4 + 2] Benzannulation of 3-Alkenylpyrroles/Thiophenes with Propargylic Alcohols: Access to Substituted Indoles, Benzothiophenes, and Aza[5]helicenes
2
Academy of Scientific and Innovative Research, New Delhi, India
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Publication type: Journal Article
Publication date: 2017-02-22
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
28195471
Organic Chemistry
Abstract
An efficient and practical one-pot [4 + 2] benzannulation method to produce highly substituted indoles and 1-benzothiophenes via sequential acid-catalyzed propargylation/base-mediated cycloisomerization reactions has been developed. This method allows access to differently substituted (mainly on phenyl ring) indoles and 1-benzothiophenes from the reaction of 3-alkenylpyrroles/-thiophenes as C4 synthons with 1-aryl/1-heteroaryl propargylic alcohols as C2 synthons. Interestingly, dialkynyl substrates can undergo tandem benzannulations to give substituted aza[5]helicenes in 82-83% yield.
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Total citations:
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Citations from 2024:
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(9.76%)
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GOST
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Reddy C. S. et al. [4 + 2] Benzannulation of 3-Alkenylpyrroles/Thiophenes with Propargylic Alcohols: Access to Substituted Indoles, Benzothiophenes, and Aza[5]helicenes // Journal of Organic Chemistry. 2017. Vol. 82. No. 5. pp. 2345-2354.
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Reddy C. S., Rani Valleti R., Sathish P. [4 + 2] Benzannulation of 3-Alkenylpyrroles/Thiophenes with Propargylic Alcohols: Access to Substituted Indoles, Benzothiophenes, and Aza[5]helicenes // Journal of Organic Chemistry. 2017. Vol. 82. No. 5. pp. 2345-2354.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.6b02637
UR - https://doi.org/10.1021/acs.joc.6b02637
TI - [4 + 2] Benzannulation of 3-Alkenylpyrroles/Thiophenes with Propargylic Alcohols: Access to Substituted Indoles, Benzothiophenes, and Aza[5]helicenes
T2 - Journal of Organic Chemistry
AU - Reddy, Chada S
AU - Rani Valleti, Reddi
AU - Sathish, Puppala
PY - 2017
DA - 2017/02/22
PB - American Chemical Society (ACS)
SP - 2345-2354
IS - 5
VL - 82
PMID - 28195471
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2017_Reddy,
author = {Chada S Reddy and Reddi Rani Valleti and Puppala Sathish},
title = {[4 + 2] Benzannulation of 3-Alkenylpyrroles/Thiophenes with Propargylic Alcohols: Access to Substituted Indoles, Benzothiophenes, and Aza[5]helicenes},
journal = {Journal of Organic Chemistry},
year = {2017},
volume = {82},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/acs.joc.6b02637},
number = {5},
pages = {2345--2354},
doi = {10.1021/acs.joc.6b02637}
}
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MLA
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Reddy, Chada S., et al. “[4 + 2] Benzannulation of 3-Alkenylpyrroles/Thiophenes with Propargylic Alcohols: Access to Substituted Indoles, Benzothiophenes, and Aza[5]helicenes.” Journal of Organic Chemistry, vol. 82, no. 5, Feb. 2017, pp. 2345-2354. https://doi.org/10.1021/acs.joc.6b02637.