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Ring Transformation of the S-(2-Oxo-2,3-dihydro-1-benzofuran-3-yl)isothiuronium Bromides to 5-(2-Hydroxyphenyl)-2-imino-1,3-thiazolidin-4-ones
Authors: Kammel Richard | Hanusek Jiří
Year: 2014
Type of publication: článek v odborném periodiku
Name of source: Heterocycles
Publisher name: The Japan Institute of Heterocyclic Chemistry
Place: Tokyo
Page from-to: 1183-1194
Titles:
Language Name Abstract Keywords
cze Transformace kruhu S-(2-oxo-2,3-dihydro-1-benzofuran-3-yl)isothiouronium-bromidů na 5-(2-hydroxyfenyl)-2-imino-1,3-thiazolidin-4-ony. Byla popsána syntéza 13 substituovaných 5-(2-hydroxyethyl)-2-fenylimino-1,3-thiazolidin-4-onů vycházející ze snadno dostupných a stabilních S-(2-oxo-2,3-dihydro-1-benzofuran-3-yl)isothiouronium-bromidů. Transformace probíhá za mírných podmínek, je velmi snadno proveditelná a je aplikovatelná na mnoho substituentů isothiouroniové části. Některé 1,3-thiazolidin-4-ony vykazují dynamické NMR chování v roztoku, a to kvůli existenci prototropie (tautomerie) a E-/Z-stereoisomerie. Thermochromní chování všech připravených látek bylo rovněž pozorováno. Transformace kruhu; S-(2-oxo-2,3-dihydro-1-benzofuran-3-yl)isothiouronium-bromid; 5-(2-hydroxyfenyl)-2-imino-1,3-thiazolidin-4-on.
eng Ring Transformation of the S-(2-Oxo-2,3-dihydro-1-benzofuran-3-yl)isothiuronium Bromides to 5-(2-Hydroxyphenyl)-2-imino-1,3-thiazolidin-4-ones Synthesis of thirteen substituted 5-(2-hydroxyethyl)-2-phenylimino-1,3-thiazolidin-4-ones is described starting from easily available and stable S-(2-oxo-2,3-dihydro-1-benzofuran-3-yl)isothiuronium bromides. The transformation proceeds under mild conditions, is very simple to perform, and is applicable to a wide range of substituents on isothiuronium moiety. Some 1,3-thiazolidin-4-ones show dynamic NMR behavior in solution because of prototropy tautomerism and E-/Z-stereoisomerism. Thermochromic behavior was observed for all synthesized compound. Transformation; S-(2-Oxo-2,3-dihydro-1-benzofuran-3-yl)isothiuronium Bromides; 5-(2-Hydroxyphenyl)-2-imino-1,3-thiazolidin-4-ones.

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