Synthesis of imidazo[1,5- a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes

Dmitrii A Aksenov; Nikolai A Arutiunov; Vladimir V Maliuga; Alexander V Aksenov; Michael Rubin

doi:10.3762/bjoc.16.239

Synthesis of imidazo[1,5- a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes

Beilstein J Org Chem. 2020 Nov 26:16:2903-2910. doi: 10.3762/bjoc.16.239. eCollection 2020.

Authors

Dmitrii A Aksenov¹, Nikolai A Arutiunov¹, Vladimir V Maliuga¹, Alexander V Aksenov¹, Michael Rubin^{1

2}

Affiliations

¹ Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355017, Russian Federation.
² Department of Chemistry, University of Kansas, 1567 Irving Hill Road, Lawrence, KS 66045, USA.

Abstract

Imidazo[1,5-a]pyridines were efficiently prepared via the cyclization of 2-picolylamines with nitroalkanes electrophilically activated in the presence of phosphorous acid in polyphosphoric acid (PPA) medium.

Keywords: cyclization; heterocycles; imidazo[1,5-a]pyridines; nitroalkanes; polyphosphoric acid.

Grants and funding

This work was supported by the Russian Foundation for Basic Research (grant #19-03-00308a) and a grant from the Ministry of Education and Science of the Russian Federation (grant #0795-2020-0031).