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Reactivity of 2‐Aminothiazole and 2‐ or 6‐Aminobenzothiazole Derivatives Towards the Triphenylbismuth Diacetate/Catalytic Copper Diacetate Phenylation System
Author(s) -
Miloudi Abdellah,
ElAbed Douniazad,
Boyer Gérard,
Finet Jean Pierre,
Galy Jean Pierre,
Siri Didier
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300656
Subject(s) - chemistry , copper , reactivity (psychology) , catalysis , reaction conditions , organic chemistry , medicinal chemistry , combinatorial chemistry , medicine , alternative medicine , pathology
The copper diacetate catalysed reaction of triphenylbismuth diacetate with 6‐aminobenzothiazole compounds afforded selectively the 6‐phenylamino derivatives in good to high yields. A similar reaction with 2‐aminothiazole or 2‐aminobenzothiazole compounds gave mixtures of the monophenylated and diphenylated products 2‐phenylaminothiazole and 2‐( N ‐phenylamino)‐3‐ N′ ‐phenylthiazole derivatives, respectively, with the diphenyl product being predominant. Semi‐empirical calculations with the SAM1/D and CHAIN methods performed on the evolution of a 2‐aminobenzothiazole − copper( III ) intermediate were in good qualitative agreement with the experimental results. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)