Direct Synthesis of Pyrrolo[1,2-α]quinoxalines via Iron-Catalyzed Transfer Hydrogenation between 1-(2-Nitrophenyl)pyrroles and Alcohols
Simin Chun
1
,
Jiwon Ahn
1
,
Ramachandra Reddy Putta
2
,
Seok-Beom Lee
1
,
Dong-Chan Oh
3
,
Suckchang Hong
1
2
Publication type: Journal Article
Publication date: 2020-10-29
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
33119283
Organic Chemistry
Abstract
Herein, we describe novel iron-catalyzed transfer hydrogenation between alcohols and 1-(2-nitrophenyl)pyrroles for the synthesis of pyrrolo[1,2-α]quinoxalines. The tricarbonyl (η4-cyclopentadienone) iron complex catalyzed the oxidation of alcohols and the reduction of nitroarenes, and the corresponding aldehydes and aniline were generated in situ. The resulting Pictet-Spengler-type annulation/oxidation completed the quinoxaline structure formation. The protocol tolerated various kinds of functional groups and provided 29 samples of 4-substituted pyrrolo[1,2-α]quinoxalines. The developed method was also applied for the synthesis of additional polyheterocycles.
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Metrics
43
Total citations:
43
Citations from 2024:
14
(32.56%)
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GOST
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Chun S. et al. Direct Synthesis of Pyrrolo[1,2-α]quinoxalines via Iron-Catalyzed Transfer Hydrogenation between 1-(2-Nitrophenyl)pyrroles and Alcohols // Journal of Organic Chemistry. 2020. Vol. 85. No. 23. pp. 15314-15324.
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Chun S., Ahn J., Putta R. R., Lee S., Oh D., Hong S. Direct Synthesis of Pyrrolo[1,2-α]quinoxalines via Iron-Catalyzed Transfer Hydrogenation between 1-(2-Nitrophenyl)pyrroles and Alcohols // Journal of Organic Chemistry. 2020. Vol. 85. No. 23. pp. 15314-15324.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.joc.0c02145
UR - https://doi.org/10.1021/acs.joc.0c02145
TI - Direct Synthesis of Pyrrolo[1,2-α]quinoxalines via Iron-Catalyzed Transfer Hydrogenation between 1-(2-Nitrophenyl)pyrroles and Alcohols
T2 - Journal of Organic Chemistry
AU - Chun, Simin
AU - Ahn, Jiwon
AU - Putta, Ramachandra Reddy
AU - Lee, Seok-Beom
AU - Oh, Dong-Chan
AU - Hong, Suckchang
PY - 2020
DA - 2020/10/29
PB - American Chemical Society (ACS)
SP - 15314-15324
IS - 23
VL - 85
PMID - 33119283
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2020_Chun,
author = {Simin Chun and Jiwon Ahn and Ramachandra Reddy Putta and Seok-Beom Lee and Dong-Chan Oh and Suckchang Hong},
title = {Direct Synthesis of Pyrrolo[1,2-α]quinoxalines via Iron-Catalyzed Transfer Hydrogenation between 1-(2-Nitrophenyl)pyrroles and Alcohols},
journal = {Journal of Organic Chemistry},
year = {2020},
volume = {85},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.joc.0c02145},
number = {23},
pages = {15314--15324},
doi = {10.1021/acs.joc.0c02145}
}
Cite this
MLA
Copy
Chun, Simin, et al. “Direct Synthesis of Pyrrolo[1,2-α]quinoxalines via Iron-Catalyzed Transfer Hydrogenation between 1-(2-Nitrophenyl)pyrroles and Alcohols.” Journal of Organic Chemistry, vol. 85, no. 23, Oct. 2020, pp. 15314-15324. https://doi.org/10.1021/acs.joc.0c02145.