Direct construction of carbazoles from 2-methyl-indole-3-carbaldehydes and enals
Dehai Liu
1, 2, 3, 4, 5, 6
,
Jie Huang
1, 2, 3, 4, 5, 6
,
Zhenqian Fu
1, 2, 3, 4, 5, 6, 7
,
Wei Huang
1, 7
2
Key Laboratory of Flexible Electronics & Institute of Advanced Materials
3
Jiangsu National Synergetic Innovation Center for Advanced Materials
5
Nanjing
|
6
CHINA
|
Publication type: Journal Article
Publication date: 2019-01-31
scimago Q1
wos Q1
SJR: 1.928
CiteScore: 16.1
Impact factor: 9.2
ISSN: 14639262, 14639270
Environmental Chemistry
Pollution
Abstract
The direct and rapid construction of carbazoles was achieved via the reaction of 2-methyl-indole-3-carbaldehydes with enals promoted by LiCl/DBU in a single operation. This mild and green reaction proceeds through a [4 + 2] cycloaddition/dehydration/oxidative aromatization cascade to generate carbazoles in good to excellent yields. The reaction features mild reaction conditions, a broad substrate scope, and excellent functional group tolerance, using O2 (1 atm) as the sole oxidant and affording H2O as the only by-product. More importantly, 4-fluoroquinocarbazole, a significant bioactive compound, was generated in 80% yield in only one step from the obtained carbazole.
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Metrics
27
Total citations:
27
Citations from 2024:
5
(18.52%)
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GOST
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Liu D. et al. Direct construction of carbazoles from 2-methyl-indole-3-carbaldehydes and enals // Green Chemistry. 2019. Vol. 21. No. 5. pp. 968-972.
GOST all authors (up to 50)
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Liu D., Huang J., Fu Z., Huang W. Direct construction of carbazoles from 2-methyl-indole-3-carbaldehydes and enals // Green Chemistry. 2019. Vol. 21. No. 5. pp. 968-972.
Cite this
RIS
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TY - JOUR
DO - 10.1039/c9gc00064j
UR - https://xlink.rsc.org/?DOI=C9GC00064J
TI - Direct construction of carbazoles from 2-methyl-indole-3-carbaldehydes and enals
T2 - Green Chemistry
AU - Liu, Dehai
AU - Huang, Jie
AU - Fu, Zhenqian
AU - Huang, Wei
PY - 2019
DA - 2019/01/31
PB - Royal Society of Chemistry (RSC)
SP - 968-972
IS - 5
VL - 21
SN - 1463-9262
SN - 1463-9270
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2019_Liu,
author = {Dehai Liu and Jie Huang and Zhenqian Fu and Wei Huang},
title = {Direct construction of carbazoles from 2-methyl-indole-3-carbaldehydes and enals},
journal = {Green Chemistry},
year = {2019},
volume = {21},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://xlink.rsc.org/?DOI=C9GC00064J},
number = {5},
pages = {968--972},
doi = {10.1039/c9gc00064j}
}
Cite this
MLA
Copy
Liu, Dehai, et al. “Direct construction of carbazoles from 2-methyl-indole-3-carbaldehydes and enals.” Green Chemistry, vol. 21, no. 5, Jan. 2019, pp. 968-972. https://xlink.rsc.org/?DOI=C9GC00064J.