Work

3-Aryl-2 H -azirines as annulation reagents in the Ni(II)-catalyzed synthesis of 1 H -benzo[4,5]thieno[3,2- b ]pyrroles

Year: 2025

Type: article

Abstract: A high-yielding method for the synthesis of 3-arylbenzo[4,5]thieno[3,2- b ]pyrroles has been developed via pyrrole ring annulation to the aromatic benzo[ b ]thiophene system, using 3-arylazirines as a N‒C=C synthon. The reaction is catalyzed by Ni(hfacac) 2 and proceeds through the azirine ring opening across the N=C3 bond. Azirines with both electron-donating and electron-withdrawing C3-aryl substituents tolerate the reaction conditions. The reaction of the N -methylindole analog also provides the annulation product but in moderate yield. The described synthesis is the first example of a dealkoxycarbonylative annulation reaction, in which 2 H -azirines act as the annulation reagent.

Source: Beilstein Journal of Organic Chemistry

DOI: 10.3762/bjoc.21.123

Authors: Julia I Pavlenko, Pavel A Sakharov, Anastasiya V Agafonova, Derenik A Isadzhanyan, Alexander F Khlebnikov, Mikhail S Novikov

Institution: St Petersburg University

Language: English

Topic: Synthesis and Characterization of Pyrroles

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: Saint Petersburg State University, Russian Science Foundation, Division of Materials Research

Awards: G4699174228, G5316223668