A. Wojtkielewicz, Paulina Uścinowicz, L. Siergiejczyk
Jan 31, 2017
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Steroids
Abstract
Graphical abstract Figure. No Caption available. HighlightsThe reaction between 16‐dehydropregnenolone acetate and 2‐aminobenzimidazole was investigated as an easy way to obtain pyrimidinobenzimidazole derivative.The reaction mechanism based on experimental evidences as well as DFT calculations was proposed.D‐homo ketone byproduct was formed in &agr;‐ketol type rearrangement.The strong solvent effect on the condensation process was revealed. 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.