Synthesis of N-Propargyl Pyrrolylamides and Theoretical Study of Pyrrolylimide Reduction by NaBH₄

Abstract

This study is divided into two parts: experimental and theoretical. In the experimental part, N-propargyl-substituted pyrrolylamide derivatives are synthesized in five steps starting from pyrrole. The main features of this procedure are (i) the synthesis of 2- and 3-nitropyrrole, (ii) the introduction of a propargyl group on the nitrogen atom of the pyrrole, (iii) coupling of various substituents with the alkyne functionality by the Sonogashira reaction, (iv) synthesis of pyrrolylimides by a tin-catalyzed reaction with phthalic anhydride, and, finally, (v) reduction of pyrrolylimides with sodium borohydride (NaBH₄) in the presence of water. The theoretical part concerns the reduction mechanism of the pyrrolylimide by NaBH₄. The hybrid functional B3LYP in density functional theory is used to determine and discuss the energetics of the compounds.

Key words

heterocycles - alkynes - coupling - molecular modeling - reduction

Publikationsverlauf

Eingereicht: 22. Februar 2023

Angenommen nach Revision: 11. Juli 2023

Artikel online veröffentlicht:
31. August 2023

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