title: A study on the reaction of 16-dehydropregnenolone acetate with 2-aminobenzimidazole.
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.
authors.affiliation: Institute of Chemistry, University of Białystok, K. Ciołkowskiego 1K, 15-245 Białystok, Poland. Electronic address: jeremy@uwb.edu.pl.
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Wojtkielewicz
authors.affiliation: Institute of Chemistry, University of Białystok, K. Ciołkowskiego 1K, 15-245 Białystok, Poland.
authors.forename: Paulina
authors.initials: P
authors.lastname: Uścinowicz
authors.affiliation: Institute of Chemistry, University of Białystok, K. Ciołkowskiego 1K, 15-245 Białystok, Poland.
authors.forename: Leszek
authors.initials: L
authors.lastname: Siergiejczyk
authors.affiliation: Institute of Chemistry, University of Białystok, K. Ciołkowskiego 1K, 15-245 Białystok, Poland.
authors.forename: Urszula
authors.initials: U
authors.lastname: Kiełczewska
authors.affiliation: Institute of Chemistry, University of Białystok, K. Ciołkowskiego 1K, 15-245 Białystok, Poland.
authors.forename: Artur
authors.initials: A
authors.lastname: Ratkiewicz
authors.affiliation: Institute of Chemistry, University of Białystok, K. Ciołkowskiego 1K, 15-245 Białystok, Poland.
authors.forename: Jacek W
authors.initials: JW
authors.lastname: Morzycki
mesh_terms: D001562:Benzimidazoles / Q000737:chemistry*; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D011284:Pregnenolone / Q000031:analogs & derivatives* / Q000737:chemistry; D013256:Steroids / Q000737:chemistry
chemical_list: D001562:Benzimidazoles; D013256:Steroids; C003592:16-dehydropregnenolone; D011284:Pregnenolone; C027391:2-aminobenzimidazole
keywords: 2-Aminobenzimidazole; Autoxidation; Condensation; Steroids; α-Ketol rearrangement