[4 + 2] Annulation of 3-Nitroindoles with Alkylidene Malononitriles: Entry to Substituted Carbazol-4-amine Derivatives
Publication type: Journal Article
Publication date: 2018-09-19
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
30229658
Organic Chemistry
Abstract
A general and transition-metal-free method for the construction of the carbazol-4-amine motif via a vinylogous Michael addition/cyclization/isomerization/elimination reaction of 3-nitroindoles with alkylidene malononitriles has been developed. This novel methodology allows the facile synthesis of a series of di- and trisubstituted carbazol-4-amine derivatives in moderate to good yields. A gram-scale experiment was successfully performed, highlighting the practicability of this method. Moreover, this strategy is also applicable to 3-nitrobenzothiophene, affording the corresponding dibenzo[ b, d]thiophen-1-amine derivatives in moderate yields.
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42
Total citations:
42
Citations from 2024:
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(26.19%)
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GOST
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Cao D. et al. [4 + 2] Annulation of 3-Nitroindoles with Alkylidene Malononitriles: Entry to Substituted Carbazol-4-amine Derivatives // Journal of Organic Chemistry. 2018. Vol. 83. No. 20. pp. 12568-12574.
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Cao D., Ying A., Mo H., CHEN D., Chen G., Wang Z., Yang J. [4 + 2] Annulation of 3-Nitroindoles with Alkylidene Malononitriles: Entry to Substituted Carbazol-4-amine Derivatives // Journal of Organic Chemistry. 2018. Vol. 83. No. 20. pp. 12568-12574.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.8b01876
UR - https://doi.org/10.1021/acs.joc.8b01876
TI - [4 + 2] Annulation of 3-Nitroindoles with Alkylidene Malononitriles: Entry to Substituted Carbazol-4-amine Derivatives
T2 - Journal of Organic Chemistry
AU - Cao, Dongdong
AU - Ying, Anguo
AU - Mo, Hanjie
AU - CHEN, DINGBEN
AU - Chen, Gang
AU - Wang, Zhiming
AU - Yang, Jian-Guo
PY - 2018
DA - 2018/09/19
PB - American Chemical Society (ACS)
SP - 12568-12574
IS - 20
VL - 83
PMID - 30229658
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2018_Cao,
author = {Dongdong Cao and Anguo Ying and Hanjie Mo and DINGBEN CHEN and Gang Chen and Zhiming Wang and Jian-Guo Yang},
title = {[4 + 2] Annulation of 3-Nitroindoles with Alkylidene Malononitriles: Entry to Substituted Carbazol-4-amine Derivatives},
journal = {Journal of Organic Chemistry},
year = {2018},
volume = {83},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acs.joc.8b01876},
number = {20},
pages = {12568--12574},
doi = {10.1021/acs.joc.8b01876}
}
Cite this
MLA
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Cao, Dongdong, et al. “[4 + 2] Annulation of 3-Nitroindoles with Alkylidene Malononitriles: Entry to Substituted Carbazol-4-amine Derivatives.” Journal of Organic Chemistry, vol. 83, no. 20, Sep. 2018, pp. 12568-12574. https://doi.org/10.1021/acs.joc.8b01876.