Facile synthesis of novel functionalized 1,3-selenazoles

Abstract

The reaction of selenourea with diethyl 2,4-dibromo-3-oxoglutarate afforded ethyl 2-(2-amino-5-ethoxycarbonyl-1,3-selenazol-4-yl)-2-bromoethanoate. Treatment of the latter with acylating agents and various nucleophiles gave a series of new 4,5-disubstituted 2-amino-1,3-selenazoles. All compounds were characterized spectroscopically. The crystal structure determination of ethyl 2-(2-amino-5-ethoxycarbonyl-1,3-selenazol-4-yl)-2-bromoethanoate is reported.

Methyl 2-Amino-4-[1-(tert-butoxycarbonyl)azetidin-3-yl]-1,3-selenazole-5-carboxylate

“…Selenazoles can be obtained using analogous synthetic strategies similar to the ones used for thiazoles. Among a variety of ring construction reactions, the most widely used approach is Hantzsch synthesis and its variations [15][16][17]. This methodology reliably leads to the formation of diverse heterocyclic rings in good yields.…”