A new multicomponent reaction: unexpected formation of derivatizable cyclic α-alkoxy isothioureas.

Org Biomol Chem

Institut für Chemie, Carl von Ossietzky Universität Oldenburg, P. O. Box 2503, Carl-von-Ossietzky-Str. 9-11, 26111 Oldenburg, Germany.

Published: March 2015

An unexpected formation of cyclic α-alkoxy isothioureas has been achieved. As is known, the heterocyclic imines 2,5-dihydro-1,3-thiazoles are convertible to bisamides with the aid of a carboxylic acid and an isocyanide (Ugi reaction). Herein, it is shown that 2,5-dihydro-1,3-thiazole S-monoxides-the respective α-sulfinyl imines-are characterized by an altered reaction behavior. In a hitherto unknown multicomponent reaction the α-sulfinyl imines react with an isocyanide under acidic conditions in an alcoholic solution to the respective α-alkoxy isothioureas in good yields. In addition to the investigations on this unexpected synthesis the regioselectivity of the acylation of the synthesized compounds is described. A rearrangement, which is accelerated by EDC and HOBt, between both possible regioisomers was found.

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Source
http://dx.doi.org/10.1039/c4ob02608jDOI Listing

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