A study on the reaction of 16-dehydropregnenolone acetate with 2-aminobenzimidazole

Agnieszka Wojtkielewicz; Paulina Uścinowicz; Leszek Siergiejczyk; Urszula Kiełczewska; Artur Ratkiewicz; Jacek W Morzycki

doi:10.1016/j.steroids.2016.09.003

A study on the reaction of 16-dehydropregnenolone acetate with 2-aminobenzimidazole

Steroids. 2017 Jan:117:71-76. doi: 10.1016/j.steroids.2016.09.003. Epub 2016 Sep 16.

Authors

Agnieszka Wojtkielewicz¹, Paulina Uścinowicz², Leszek Siergiejczyk², Urszula Kiełczewska², Artur Ratkiewicz², Jacek W Morzycki²

Affiliations

¹ Institute of Chemistry, University of Białystok, K. Ciołkowskiego 1K, 15-245 Białystok, Poland. Electronic address: jeremy@uwb.edu.pl.
² Institute of Chemistry, University of Białystok, K. Ciołkowskiego 1K, 15-245 Białystok, Poland.

PMID: 27644145
DOI: 10.1016/j.steroids.2016.09.003

Abstract

The condensation of 16-dehydropregnenolone acetate with 2-aminobenzimidazole was studied. The polycyclic aromatic product was formed as a single regioisomer in a cascade reaction comprising addition, cyclization, autoxidation, and aromatization, in addition to the rearranged D-homo product. The reaction mechanism based on DFT calculations is proposed.

Keywords: 2-Aminobenzimidazole; Autoxidation; Condensation; Steroids; α-Ketol rearrangement.

Publication types

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

MeSH terms

Benzimidazoles / chemistry*
Cyclization
Models, Molecular
Molecular Structure
Pregnenolone / analogs & derivatives*
Pregnenolone / chemistry
Steroids / chemistry

Substances

Benzimidazoles
Steroids
16-dehydropregnenolone
Pregnenolone
2-aminobenzimidazole