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

Authors

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

DOI:

https://doi.org/10.1007/5931

Keywords:

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

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.

Author Biographies

Nicolai A. Aksenov, Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355017, Russia

Professor

Nikolai A. Arutiunov, Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355017, Russia

Post-graduate student

Nikita K. Kirillov, Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355017, Russia

Post-graduate student

Dmitrii A. Aksenov, Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355017, Russia

Assistant professor

Alexander V. Aksenov, Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355017, Russia

Professor

Michael Rubin, Department of Chemistry, University of Kansas, 1567 Irving Hill Rd., Lawrence, KS 66045-7582, USA

Associate professor

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Published

2020-09-17

Issue

Vol. 56 No. 8 (2020)

Section

Original Papers