TY - JOUR
T1 - A New Method for the Preparation of 2-(Alkylamino)benzoxazoles and 2-(Alkylimino)benzoxazolines
AU - Yamato, Masatoshi
AU - Takeuchi, Yasuo
AU - Hattori, Kyoko
AU - Hashigaki, Kuniko
N1 - Copyright:
Copyright 2016 Elsevier B.V., All rights reserved.
PY - 1984
Y1 - 1984
N2 - New syntheses of 2-(alkylamino)benzoxazoles (III) and 3-alkyI-2-(alkylimino)benzoxazolines (IV) were developed. Various compounds III were obtained by the reactions of 2-(methylthio)benzoxazole with amines. In the alkylation of 2-(monoalkylamino)benzoxazoles, the use of a base as a catalyst was found to be important for the selective preparation of 2-(N, N-dialkylamino)benzoxazoles; in the absence of base, IV was obtained. On the other hand, alkylation of N, N ′-dialkyl-N-(2-hydroxyphenyl)thioureas resulted in the development of another method for the preparation of IV.
AB - New syntheses of 2-(alkylamino)benzoxazoles (III) and 3-alkyI-2-(alkylimino)benzoxazolines (IV) were developed. Various compounds III were obtained by the reactions of 2-(methylthio)benzoxazole with amines. In the alkylation of 2-(monoalkylamino)benzoxazoles, the use of a base as a catalyst was found to be important for the selective preparation of 2-(N, N-dialkylamino)benzoxazoles; in the absence of base, IV was obtained. On the other hand, alkylation of N, N ′-dialkyl-N-(2-hydroxyphenyl)thioureas resulted in the development of another method for the preparation of IV.
KW - 2-(alkylamino)benzoxazole
KW - 2-(methylthio)benzoxazole
KW - 3-alkyl-2-(alkylimino)benzoxazoline
KW - 3-alkylbenzoxazoline-2-thione
KW - N, N'-dialkyl-N-(2-hydroxyphenyl)thiourea
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U2 - 10.1248/cpb.32.3053
DO - 10.1248/cpb.32.3053
M3 - Article
AN - SCOPUS:85004413010
SN - 0009-2363
VL - 32
SP - 3053
EP - 3060
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
IS - 8
ER -