SCOPE AND LIMITATIONS OF A MODIFIED HANTZSCH REACTION FOR THE SYNTHESIS OF OXAZOLE-DEHYDROAMINO ACID DERIVATIVES FROM DEHYDROAMINO ACID AMIDES

[摘要]：A variety of oxazole derivatives that possess an alpha,beta-unsaturated substituent at the 2-position were conveniently synthesized in good yields via a Hantzsch-type reaction between dehydroamino acid amides and P-bromopyruvate derivatives. Furthermore, oxazoles with substituents at the 2- and 5-positions were also obtained in good yields using the corresponding beta-substituted beta-bromopyruvate derivatives. A revised reaction mechanism to explain the enhanced reactivity of dehydroamino acid amides for the Hantzsch-oxazole-type reaction is presented.

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