Synthesis of 1,2,4-Oxadiazoles by Tandem Reaction of Nitroalkenes with Arenes and Nitriles in the Superacid TfOH

Andrei A Golushko; Olesya V Khoroshilova; Aleksander V Vasilyev

doi:10.1021/acs.joc.9b00812

Synthesis of 1,2,4-Oxadiazoles by Tandem Reaction of Nitroalkenes with Arenes and Nitriles in the Superacid TfOH

J Org Chem. 2019 Jun 7;84(11):7495-7500. doi: 10.1021/acs.joc.9b00812. Epub 2019 May 24.

Authors

Andrei A Golushko¹, Olesya V Khoroshilova², Aleksander V Vasilyev^{1

3}

Affiliations

¹ Department of Organic Chemistry, Institute of Chemistry , Saint Petersburg State University , Universitetskaya nab., 7/9 , Saint Petersburg 199034 , Russia.
² Center for X-ray Diffraction Studies, Research Park , Saint Petersburg State University , Universitetskiy pr., 26 , Saint Petersburg , Petrodvoretz 198504 , Russia.
³ Department of Chemistry , Saint Petersburg State Forest Technical University , Institutsky per., 5 , Saint Petersburg 194021 , Russia.

PMID: 31117566
DOI: 10.1021/acs.joc.9b00812

Abstract

The tandem reaction of nitroalkenes with arenes and nitriles in the superacid CF₃SO₃H (TfOH) results in the formation of 1,2,4-oxadiazole derivatives in yields up to 96%. This reaction proceeds via the consequent interaction of arenes and nitriles, as nucleophiles, with intermediate cationic species derived by the protonation of nitroalkenes in TfOH. This is novel and general synthesis of 1,2,4-oxadiazoles, which are very important compounds for medicinal chemistry.

Publication types

Research Support, Non-U.S. Gov't