This article is cited in 3 papers

Communications

The Castagnoli–Cushman reaction of bicyclic pyrrole dicarboxylic anhydrides bearing electron-withdrawing substituents

M. E. Chizhova^a, D. V. Dar'in^a, M. Yu. Krasavin<sup>ab

a</sup> Institute of Chemistry, St. Petersburg State University, St. Petersburg, Russian Federation
^b Immanuel Kant Baltic Federal University, Kaliningrad, Russian Federation

Abstract: Four anhydrides of 1-(carboxymethyl)pyrrole-2-carboxylic acids bearing electron-withdrawing substituents at positions 6 or 7 of the bicyclic system have been investigated in the Castagnoli–Cushman reaction with imines. 6-Benzoyl- and 7-sulfamoyl-substituted anhydrides demonstrated lower reactivity while 7-benzoyl derivative displayed broader substrate scope. These findings have been rationalized from the mechanistic perspective.

Keywords: cyclic anhydrides, imines, Castagnoli–Cushman reaction, δ-lactams, enolization, resonance stabilization.

Language: English

DOI: 10.1016/j.mencom.2020.07.030

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