Publication detail

Unexpected reactions of 3-bromooxindole with 4-methoxythiobenzamide and thiourea

Authors: Hanusek Jiří | Kammel Richard | Tarabová Denisa

Year: 2015

Type of publication: ostatní - přednáška nebo poster

Page from-to: nestránkováno

Titles:

Language	Name	Abstract	Keywords
eng	Unexpected reactions of 3-bromooxindole with 4-methoxythiobenzamide and thiourea	In present the reactions of 3-bromo-1,3-dihydro-2H-indol-2-one (1b) with 4-methoxythiobenzamide and thiourea under mildly basic conditions is studied. While analogous 3-bromo-1-benzofuran-2(3H)-one (1a) gave the expected 5-(2-hydroxyphenyl)-2-(4-methoxyphenyl)-1,3-thiazol-4-ol (2) or 2-amino-5-(2-hydroxyphenyl)-1,3-thiazol-4(5H)-one (5) the lactam 1b reacted with thioamide via an unexpected Eschenmoser coupling reaction to give (3Z)-3-[amino(4-methoxyphenyl)-methylidene]-1,3-dihydro-2H-indol-2-one (3). When lactam 1b is treated with thiourea, isoindigo (4) is the only isolated product. The reaction mechanisms, involving formation of α-thioiminium or isothiouronium salts and their base-catalyzed decomposition is also proposed.

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