Synthesis of 2,3-Disubstituted Pyrroles by Lewis Acid Promoted Cyclization of N-Sulfonyl Vinylogous Carbamates and Amides.

ABSTRACT: A three-step sequence to construct pyrroles from three components including 2,2-dimethoxyethylamine, aryl/alkyl sulfonyl chlorides and alkynes bearing electron-withdrawing groups is presented. The pyrroles are proposed to arise via a 5-exo-trig cyclization proceeding through both oxocarbenium and N-sulfonyliminium ions. This modular route allows for the variability at the N-sulfonyl group, the C2 and C3 substituents for rational vectoring of the pyrrole nucleus for downstream processes.

SUBMITTER: Rustin GJ 

PROVIDER: S-EPMC10237359 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature