Benzo[1, 4]diazocinone/Pyrrole Ensembles via the Catalyst‐Free Insertion of Pyrrolylacetylenic Ketones into Benzimidazoles. Issue 48 (21st December 2022)

• Record Type: Journal Article
• Authors: Belyaeva, Kseniya V.; Nikitina, Lina P.; Gen', Veronika S.; Saliy, Ivan V.; Sobenina, Lyubov N.; Afonin, Andrei V.; Kuzmin, Anton V.; Vashchenko, Alexander V.; Trofimov, Boris A.
• Is Part Of: ChemistrySelect. Volume 7:Issue 48(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-12-21
• Subjects: alkynes -- nitrogen heterocycles -- ring expansion -- ylides -- zwitterions; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202204482
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Early unknown pharmaceutically oriented heterocyclic systems of benzo[1, 4]diazocinone/pyrrole ensembles have been synthesized in up to 93 % yields by the catalyst‐free mild insertion of pyrrolylacetylenic ketones into benzimidazoles. The reaction represents an extraordinary easy expansion of the aromatic five‐membered heterocyclic ring up to pyrrole‐ringed, highly unsaturated eight‐membered heterocyclic system. The proposed mechanism of the reaction proceeding through dipole and ylide intermediates is confirmed by quantum chemical calculations (DFT). Abstract : A versatile synthetic route to benzodiazocinones, substituted with pyrrole ring, in up to 93 % yields has been developed by two‐component reaction between 1‐substituted benzimidazoles with available acylpyrrolylacetylenes. Virtually, acylpyrrolylacetylenes scissor C(2)‐N bond to be inserted into the benzimidazole cycle by the acylethenyl moiety to construction the eight‐membered ring.