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ELECTROPHILICALLY ACTIVATED NITROALKANES IN THE SYNTHESIS OF SUBSTITUTED 1,3,4-OXADIAZOLES FROM AMINO ACID DERIVATIVES

Alexander V. Aksenov, Nikita K. Kirilov, Nicolai A. Aksenov, Nikolai A. Arutiunov, Dmitrii A. Aksenov, Michael A. Rubin
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Abstract


Novel preparative approach for the synthesis of alkylamines with 1,3,4-oxadiazole heterocyclic substituent is described. This method is based on unusual cascade transformation involving formal (4+1) cyclocondensation of hydrazides of amino acids with nitroalkanes electrophilically activated in the presence of polyphosphoric acid.



Keywords


amino acids; nitroalkanes; 1,3,4-oxadiazoles; semicarbazides; 1,3,4-thiadiazoles; Brønsted acid catalysis; cascade reaction; nucleophilic cycloaddition.

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