Chemistry - A European Journal, volume 22, issue 15, pages 5146-5150
Unprecedented Oxycyanation of Methylenecyclopropanes for the Facile Synthesis of Benzoxazine Compounds Containing a Cyano Group
Publication type: Journal Article
Publication date: 2016-02-26
Journal:
Chemistry - A European Journal
Quartile SCImago
Q1
Quartile WOS
Q2
Impact factor: 4.3
ISSN: 09476539, 15213765
General Chemistry
Catalysis
Organic Chemistry
Abstract
A novel intramolecular oxycyanation of methylenecyclopropanes is reported that proceeds through oxidative cleavage of the N-CN bond and subsequent palladium transfer from N to O of the amide group. A range of substituted benzo[d][1,3]oxazines with a cyano group are readily furnished by this newly developed oxycyanation reaction. Tris(4-trifluoromethylphenyl)phosphine as a ligand has been found to be crucial to effectively promote the transformation with high chemo- and regioselectivity. Moreover, the reaction outcome can be significantly affected by the electronic effect of the acyl group attached to the nitrogen atom of methylenecyclopropanes. When R(3) is a chloromethyl group, the pyrrolo[2,3-b]quinoline derivative is obtained by thermal-induced [3+2] cycloaddition of methylenecyclopropane to the methanediimine intermediate.
Top-30
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Citations by publishers
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Royal Society of Chemistry (RSC)
11 publications, 44%
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Wiley
6 publications, 24%
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American Chemical Society (ACS)
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1 publication, 4%
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- We do not take into account publications without a DOI.
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- Statistics recalculated weekly.
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Yuan Yu. C. et al. Unprecedented Oxycyanation of Methylenecyclopropanes for the Facile Synthesis of Benzoxazine Compounds Containing a Cyano Group // Chemistry - A European Journal. 2016. Vol. 22. No. 15. pp. 5146-5150.
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Yuan Yu. C., Yang H. B., Tang X., Wei Yin 尹., Shi M. Unprecedented Oxycyanation of Methylenecyclopropanes for the Facile Synthesis of Benzoxazine Compounds Containing a Cyano Group // Chemistry - A European Journal. 2016. Vol. 22. No. 15. pp. 5146-5150.
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TY - JOUR
DO - 10.1002/chem.201505224
UR - https://doi.org/10.1002/chem.201505224
TI - Unprecedented Oxycyanation of Methylenecyclopropanes for the Facile Synthesis of Benzoxazine Compounds Containing a Cyano Group
T2 - Chemistry - A European Journal
AU - Yuan, Yu Chao
AU - Yang, Hai Bin
AU - Tang, Xiang-Ying
AU - Shi, Min
AU - Wei Yin, 尹维
PY - 2016
DA - 2016/02/26 00:00:00
PB - Wiley
SP - 5146-5150
IS - 15
VL - 22
SN - 0947-6539
SN - 1521-3765
ER -
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@article{2016_Yuan,
author = {Yu Chao Yuan and Hai Bin Yang and Xiang-Ying Tang and Min Shi and 尹维 Wei Yin},
title = {Unprecedented Oxycyanation of Methylenecyclopropanes for the Facile Synthesis of Benzoxazine Compounds Containing a Cyano Group},
journal = {Chemistry - A European Journal},
year = {2016},
volume = {22},
publisher = {Wiley},
month = {feb},
url = {https://doi.org/10.1002/chem.201505224},
number = {15},
pages = {5146--5150},
doi = {10.1002/chem.201505224}
}
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MLA
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Yuan, Yu. Chao, et al. “Unprecedented Oxycyanation of Methylenecyclopropanes for the Facile Synthesis of Benzoxazine Compounds Containing a Cyano Group.” Chemistry - A European Journal, vol. 22, no. 15, Feb. 2016, pp. 5146-5150. https://doi.org/10.1002/chem.201505224.