5-Amino-Substituted 2-Methoxy-1,3,4-oxadiazoles as Common Precursors Toward 1,3,4-Oxadiazol-2(3H)-ones and 1,2,4-Triazolidine-3,5-diones

The divergent synthesis of two different classes of azole derivatives using 5-amino-substituted 2-methoxy-1,3,4-oxadiazoles as common substrates is reported. Depending on the reaction time and temperature, alkylation of oxadiazoles with excess alkyl halides proceeds with high regioselectivity toward 1,3,4-oxadiazolones and 1,2,4-triazolidine-3,5-diones. This operationally simple protocol enables rapid access to a diverse set of isomeric azoles using minimum synthetic steps and easily accessible oxadiazole key precursors.

Automated summary

This study reports the divergent synthesis of two different classes of azole derivatives using 5-amino-substituted 2-methoxy-1,3,4-oxadiazoles as common substrates. Depending on the reaction time and temperature, alkylation of oxadiazoles with excess alkyl halides proceeds with high regioselectivity toward 1,3,4-oxadiazolones and 1,2,4-triazolidine-3,5-diones. This operationally simple protocol enables rapid access to a diverse set of isomeric azoles using minimum synthetic steps and easily accessible oxadiazole key precursors.