期刊
TETRAHEDRON
卷 66, 期 16, 页码 3016-3023出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.02.058
关键词
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资金
- Cyprus Research Promotion Foundation [TEXNOLambdaOGammaIA/ThetaEPiISigma/0308(BE)/08]
Attempted detosylation of the 3-amino-1-(p-tosylamino)indole-2-carbonitriles 4a-c using either K2CO3 in EtOH or DBU in PhH at reflux gives unexpectedly the 3-(N-p-tosylamino)indole-2-carbonitriles 5a-c, respectively in high yields. Nevertheless, treatment of 1-(p-tosylamino)indoles 4a-c with thiophenol and DBU in PhH at reflux gives the detosylated 3-aminoindole-2-carbonitriles 5a-c. Reaction mechanisms supporting the tosyl migration (4 -> 5) and the reductive detosylation (4 -> 2) are proposed. All new compounds are fully characterised. (C) 2010 Elsevier Ltd. All rights reserved.
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