Tandem [4+1+1] Annulation Approach to 4-Acyl-3,4-dihydropyrrolo[1,2- a]pyrazines: Diastereoselective Construction of Dihydropyrazine Units from Pyrroles

Anuradha Dagar, Gi Hun Bae, Jeong Hwa Lee, Ikyon Kim

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Efficient construction of new chemical space by way of strategic use of tandem reactions is highly important in drug discovery. Described herein is an atom-economical [4+1+1] annulation approach to 3-(hetero)aryl-4-acyl-3,4-dihydropyrrolo[1,2-a]pyrazines, a new chemical space, via a one-pot three-component reaction under mild reaction conditions. Formation of multiple bonds (one C-C and two C-N) was achieved by a cascade reaction sequence consisting of generation of a Schiff base, a diastereoselective Mannich reaction, and intramolecular imine formation. This modular and environment-friendly process allowed rapid access to a wide range of 4-acylated 3,4-dihydropyrrolo[1,2-a]pyrazines and their analogues, opening opportunity to explore biological activity associated with this scaffold.

Original languageEnglish
Pages (from-to)6916-6927
Number of pages12
JournalJournal of Organic Chemistry
Volume84
Issue number11
DOIs
Publication statusPublished - 2019 Jun 7

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Tandem [4+1+1] Annulation Approach to 4-Acyl-3,4-dihydropyrrolo[1,2- a]pyrazines: Diastereoselective Construction of Dihydropyrazine Units from Pyrroles'. Together they form a unique fingerprint.

  • Cite this