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SYNTHESIS OF 4-HETERYL-SUBSTITUTED DERIVATIVES OF METHYLPYRAZOLO[1,5-a]PYRAZINE-4-CARBOXYLATES

Назар М. Цизорик, Евгений В. Гринишин, Анна Р. Мусийчук, Андрей В. Больбут, Максим А. Нечаев, Михаил В. Вовк
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Abstract


Methylpyrazolo[1,5-a]pyrazine-4-carboxylates were synthesized by palladium-catalyzed carbonylation of 4-chloropyrazolo[1,5-a]pyrazines at elevated pressure and converted via nitrile intermediates to the corresponding amidoximes and amidines. Cyclocondensation of the obtained amidoximes with trifluoroacetic anhydride or ethyl chloroformate and amidines with acetoacetate or ethyl ethoxymethylidenemalonate were used to synthesize new 4-(1,2,4-oxadiazolyl)- and 4-(pyrimidin-2-yl)-substituted pyrazolo[1,5-a]pyrazines.

Keywords


4-heteryl-substituted pyrazolo[1,5-a]pyrazines; pyrazolo[1,5-a]pyrazine-4-carboxylic acid derivatives; cyclocondensation; palladium-catalyzed carbonylation.

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