Oxidative Cyclization of 4-(2-Aminophenyl)-4-oxo-2-phenylbutanenitriles into 2-(3-Oxoindolin-2-ylidene)acetonitriles

Nicolai A Aksenov; Alexander V Aksenov; Lidiya A Prityko; Dmitrii A Aksenov; Daria S Aksenova; Mezvah A Nobi; Michael Rubin

doi:10.1021/acsomega.2c01238

Oxidative Cyclization of 4-(2-Aminophenyl)-4-oxo-2-phenylbutanenitriles into 2-(3-Oxoindolin-2-ylidene)acetonitriles

ACS Omega. 2022 Apr 15;7(16):14345-14356. doi: 10.1021/acsomega.2c01238. eCollection 2022 Apr 26.

Authors

Nicolai A Aksenov¹, Alexander V Aksenov¹, Lidiya A Prityko¹, Dmitrii A Aksenov¹, Daria S Aksenova¹, Mezvah A Nobi², 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, Kansas 66045, United States.

Abstract

A facile and highly efficient method for the preparation of 2-(3-oxoindolin-2-ylidene)acetonitriles from 4-(2-aminophenyl)-4-oxo-2-phenylbutanenitriles is described. The featured transformation operates via nucleophilic intramolecular cyclization and involves oxidation of the aniline moiety. Overall, this modification allowed for the improvement of yields and expansion of the reaction scope.