Electrophilically activated nitroalkanes in reaction with aliphatic diamines en route to imidazolines

Alexander V Aksenov; Nicolai A Aksenov; Nikolai A Arutiunov; Vladimir V Malyuga; Sergey N Ovcharov; Michael Rubin

doi:10.1039/c9ra08630g

Electrophilically activated nitroalkanes in reaction with aliphatic diamines en route to imidazolines

RSC Adv. 2019 Nov 29;9(67):39458-39465. doi: 10.1039/c9ra08630g. eCollection 2019 Nov 27.

Authors

Alexander V Aksenov¹, Nicolai A Aksenov¹, Nikolai A Arutiunov¹, Vladimir V Malyuga¹, Sergey N Ovcharov¹, Michael Rubin^{1

2}

Affiliations

¹ Department of Chemistry, North Caucasus Federal University 1a Pushkin St. Stavropol 355009 Russian Federation alexaks05@rambler.ru.
² Department of Chemistry, University of Kansas 1567 Irving Hill Road Lawrence KS 66045-7582 USA mrubin@ku.edu +1-785-864-5071.

Abstract

A novel synthetic methodology for the assembly of imidazolines via an unusual reaction between nitroalkanes and aliphatic 1,2-diamines in the presence of phosphorous acid is described. In contrast to the related highly efficient preparation of benzimidazoles from aromatic amines, this process represents a major synthetic challenge and for a long time was elusive. Analysis of the method limitations is provided.