An isoxazole strategy for the synthesis of alkyl 5-amino-4-cyano-1 H-pyrrole-2-carboxylates - versatile building blocks for assembling pyrrolo-fused heterocycles

Anastasiya V Agafonova; Liya D Funt; Mikhail S Novikov; Alexander F Khlebnikov

doi:10.1039/d1ob00053e

An isoxazole strategy for the synthesis of alkyl 5-amino-4-cyano-1 H-pyrrole-2-carboxylates - versatile building blocks for assembling pyrrolo-fused heterocycles

Org Biomol Chem. 2021 Mar 11;19(9):1976-1984. doi: 10.1039/d1ob00053e.

Authors

Anastasiya V Agafonova¹, Liya D Funt¹, Mikhail S Novikov¹, Alexander F Khlebnikov¹

Affiliation

¹ St Petersburg State University, Institute of Chemistry, 7/9 Universitetskaya nab., St Petersburg, 199034, Russia. a.khlebnikov@spbu.ru.

PMID: 33566047
DOI: 10.1039/d1ob00053e

Abstract

A full atom-economical domino method has been developed for the preparation of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates by transannulation of 5-alkoxyisoxazoles with malononitrile under Fe(ii) catalysis. Alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates are excellent building blocks for various annulation reactions, leading to new derivatives of 1H-pyrrolo[1,2-a]imidazole and pyrrolo[2,3-d]pyrimidine. The DFT calculations of mechanistic details of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylate formation are presented.

Publication types

Research Support, Non-U.S. Gov't