TRISUBSTITUTED THIAZOLES BY A 6?-ELECTROCYCLIZATION OF IMINOTHIOCARBONYL YLIDES
Iminothiocarbonyl ylides are generated by a sulfur ligand exchange reaction of sulfonium salts and undergo a 6?-electrocyclic closure and aromatization to tri substituted thiazoles.Related carbonyl ylides preferred a 4?-electrocyclization.
STUDY OF THE ESCHENMOSER SULFIDE CONTRACTION METHOD WITH AND WITHOUT A THIOPHILE
Results obtained and observations made by applying the title method for the synthesis of enaminones 5a-o, using triphenylphosphine as a thiophile and triethylamine as a base, are reported.The product distributions of the deprotonations of α-phenacylthio iminium bromides with and without thiophile and those known from thiouronium and heterocyclic thionium analogs are compared.Key words: Enaminones; α-phenacylthio iminium bromides; disulfides; thiiranes.
Corsaro, A.,Perrini, G.,Testa, M. G.,Chiacchio, U.
p. 197 - 206
(2007/10/02)
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