Substituent-Dependent Divergent Synthesis of 2-(3-Amino-2,4-dicyanophenyl)pyrroles, Pyrrolyldienols and 3-Amino-1-acylethylidene-2-cyanopyrrolizines via Reaction of Acylethynylpyrroles with Malononitrile

Maxim D Gotsko; Ivan V Saliy; Igor A Ushakov; Lyubov N Sobenina; Boris A Trofimov

doi:10.3390/molecules27238528

Substituent-Dependent Divergent Synthesis of 2-(3-Amino-2,4-dicyanophenyl)pyrroles, Pyrrolyldienols and 3-Amino-1-acylethylidene-2-cyanopyrrolizines via Reaction of Acylethynylpyrroles with Malononitrile

Molecules. 2022 Dec 3;27(23):8528. doi: 10.3390/molecules27238528.

Authors

Maxim D Gotsko¹, Ivan V Saliy¹, Igor A Ushakov¹, Lyubov N Sobenina¹, Boris A Trofimov¹

Affiliation

¹ A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia.

Abstract

An efficient method for the synthesis of pharmaceutically and high-tech prospective 2-(3-amino-2,4-dicyanophenyl)pyrroles (in up to 88% yield) via the reaction of easily available substituted acylethynylpyrroles with malononitrile has been developed. The reaction proceeds in the KOH/MeCN system at 0 °C for 2 h. In the case of 2-acylethynylpyrroles without substituents in the pyrrole ring, the reaction changes direction: instead of the target 2-(3-amino-2,4-dicyanophenyl)pyrroles, the unexpected formation of pyrrolyldienols and products of their intramolecular cyclization, 3-amino-1-acylethylidene-2-cyanopyrrolizines, is observed.

Keywords: 2-(3-amino-2,4-dicyanophenyl)pyrroles; 3-amino-1-acylethylidene-2-cyanopyrrolizines; acylethynylpyrroles; malononitrile; pyrrolyldienols.

MeSH terms

Catalysis
Cyclization
Molecular Structure
Prospective Studies
Pyrroles*

Substances

Pyrroles
dicyanmethane

Grants and funding

This research received no external funding.