期刊
TETRAHEDRON
卷 66, 期 3, 页码 685-688出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.11.067
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资金
- Cyprus Research Promotion Foundation [TEXNOLambdaGammaOIA/ThetaSigmaPiISigma(BE)/08(BE)/08]
Anthranilonitrile 3a, 4,5-dimethoxyanthranilonitrile 3b and 5-nitroanthranilonitrile 3c, react with paraformaldehyde, KCN and ZnCl2 in acetic acid under acid catalysis (H2SO4) in a sealed tube at ca. 55 degrees C to give the corresponding 2-(cyanomethylamino)benzonitriles 4a-c in 96, 86 and 57% yields, respectively. Thorpe-Ziegler cyclisation of the N-unprotected 2-(cyanomethylamino)benzonitriles 4a-c with K2CO3 in EtOH at elevated temperatures and pressures using either microwave heating or conventional heating in a sealed tube gives 3-amino, 3-amino-5,6-dimethoxy, and 3-amino-5-nitro-indole-2-carbonitriles 2a-c in moderate to good yields. All new compounds are fully characterised. (C) 2009 Elsevier Ltd. All rights reserved.
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