Gold-Catalyzed Cyclization of 1-(Indol-3-yl)-3-alkyn-1-ols: Facile Synthesis of Diversified Carbazoles
Publication type: Journal Article
Publication date: 2013-07-10
scimago Q1
wos Q2
SJR: 0.981
CiteScore: 6.7
Impact factor: 3.7
ISSN: 09476539, 15213765
PubMed ID:
23843184
General Chemistry
Catalysis
Organic Chemistry
Abstract
Efficient cyclization of 1-(indol-3-yl)-3-alkyn-1-ols in the presence of a cationic gold(I) complex, leading to annulated or specific substituted carbazoles, was observed. Depending on the reaction conditions and substitution pattern, divergent reaction pathways were discovered, furnishing diversified carbazole structures. Cycloalkyl-annulated [b]carbazoles are obtained through 1,2-alkyl migration of the metal-carbene intermediates; cycloalkyl-annulated [a]carbazoles are formed through a Wagner-Meerwein-type 1,2-alkyl shift; carbazole ethers are constructed through ring-opening of the cyclopropyl group by nucleophilic attack of water or an alcohol.
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Total citations:
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Citations from 2024:
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(14.03%)
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GOST
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Zhang Z. et al. Gold-Catalyzed Cyclization of 1-(Indol-3-yl)-3-alkyn-1-ols: Facile Synthesis of Diversified Carbazoles // Chemistry - A European Journal. 2013. Vol. 19. No. 32. pp. 10625-10631.
GOST all authors (up to 50)
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Zhang Z., Tang X., Xu Q., Shi M. Gold-Catalyzed Cyclization of 1-(Indol-3-yl)-3-alkyn-1-ols: Facile Synthesis of Diversified Carbazoles // Chemistry - A European Journal. 2013. Vol. 19. No. 32. pp. 10625-10631.
Cite this
RIS
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TY - JOUR
DO - 10.1002/chem.201301203
UR - https://doi.org/10.1002/chem.201301203
TI - Gold-Catalyzed Cyclization of 1-(Indol-3-yl)-3-alkyn-1-ols: Facile Synthesis of Diversified Carbazoles
T2 - Chemistry - A European Journal
AU - Zhang, Zhen
AU - Tang, Xiangying
AU - Xu, Qin
AU - Shi, Min
PY - 2013
DA - 2013/07/10
PB - Wiley
SP - 10625-10631
IS - 32
VL - 19
PMID - 23843184
SN - 0947-6539
SN - 1521-3765
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2013_Zhang,
author = {Zhen Zhang and Xiangying Tang and Qin Xu and Min Shi},
title = {Gold-Catalyzed Cyclization of 1-(Indol-3-yl)-3-alkyn-1-ols: Facile Synthesis of Diversified Carbazoles},
journal = {Chemistry - A European Journal},
year = {2013},
volume = {19},
publisher = {Wiley},
month = {jul},
url = {https://doi.org/10.1002/chem.201301203},
number = {32},
pages = {10625--10631},
doi = {10.1002/chem.201301203}
}
Cite this
MLA
Copy
Zhang, Zhen, et al. “Gold-Catalyzed Cyclization of 1-(Indol-3-yl)-3-alkyn-1-ols: Facile Synthesis of Diversified Carbazoles.” Chemistry - A European Journal, vol. 19, no. 32, Jul. 2013, pp. 10625-10631. https://doi.org/10.1002/chem.201301203.