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Synthesis of 2,3-Disubstituted Pyrroles by Lewis Acid Promoted Cyclization of
Gavin J Rustin1, Matthew G Donahue1
1Department of Chemistry and Biochemistry University of Southern Mississippi, Hattiesburg, MS 39406 USA.
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.
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