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Interaction of methyl 3-ethoxy-2-(2,5-dichloro-3-thenoyl)acrylate ( I ) with 3-aminopyrazole and 3-amino-1,2,4-triazole generated the respective pyrazolo[1,5-α]pyrimidine ( 4 ) and triazolo[1,5-α]pyrimidine ( 7 ). The formation of  4  entails selective and consecutive displacement of the 3-ethoxy and methoxy (ester) anions in  I  by 3-NH 2  and 1-NH of 3-aminopyrazole. On the other hand, the formation of  7  implies selective displacement of 3-ethoxy in  I  by the ring-NH followed by cyclocondensation involving the keto group in  I  and 3-NH 2  of aminotriazole. This latter selective displacement sequence is also followed by 3-amino-5-hydroxypyrazole in its reaction with  I . The structures of the new compounds are supported by microanalytical and spectral data.

zeitschrift für naturforschung b

Selective cyclization modes of methyl 3′-heteroarylamino-2′-(2,5-dichlorothiophene-3-carbonyl)acrylates. Synthesis of model (thienyl)pyrazolo- and triazolo[1,5-α]pyrimidines