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PREPARATION OF 1,3,4-OXADIAZOLES AND 1,3,4-THIADIAZOLES VIA CHEMOSELECTIVE СYCLOCONDENSATION OF ELECTROPHILICALLY ACTIVATED NITROALKANES TO (THIO)SEMICARBAZIDES OR THIOHYDRAZIDES

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


Unusual reaction proceeding via the electrophilic activation of nitroalkanes in the presence of polyphosphoric acid has been discovered. Subsequent nucleophilic attack with semicarbazides or thiosemicarbazides allows to access 2-amino-1,3,4-oxadiazoles and 2-amino-1,3,4-thiadiazoles, respectively.


Keywords


nitroalkanes; 1,3,4-oxadiazoles; semicarbazides; 1,3,4-thiadiazoles; thiosemicarbazides; Brønsted acid catalysis; cascade reaction; nucleophilic cycloadition.

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