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

Authors

  • Alexander V. Aksenov Department of Chemistry, North Caucasus Federal University, 1a Pushkina St., Stavropol 355017, Russia
  • Nikita K. Kirilov Department of Chemistry, North Caucasus Federal University, 1a Pushkina St., Stavropol 355017, Russia
  • Nicolai A. Aksenov Department of Chemistry, North Caucasus Federal University, 1a Pushkina St., Stavropol 355017, Russia
  • Nikolai A. Arutiunov Department of Chemistry, North Caucasus Federal University, 1a Pushkina St., Stavropol 355017, Russia
  • Dmitrii A. Aksenov Department of Chemistry, North Caucasus Federal University, 1a Pushkina St., Stavropol 355017, Russia
  • Michael A. Rubin Department of Chemistry, North Caucasus Federal University, 1a Pushkina St., Stavropol 355017, Russia Department of Chemistry, University of Kansas, 1567 Irving Hill Rd., Lawrence KS 66045-7582, U

DOI:

https://doi.org/10.1007/6429

Keywords:

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

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.


Author Biography

Michael A. Rubin, Department of Chemistry, North Caucasus Federal University, 1a Pushkina St., Stavropol 355017, Russia Department of Chemistry, University of Kansas, 1567 Irving Hill Rd., Lawrence KS 66045-7582, U

Associate Professor,

Department of Chemistry

University of Kansas

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Published

2022-01-27

Issue

Vol. 58 No. 1 (2022)

Section

Original Papers