Selective synthesis of N-substituted pyrrolo[1,2-a]pyrazin-1(2H)-one derivatives via alkyne cyclization

Cetinkaya Y., BALCI M.

TETRAHEDRON LETTERS, vol.55, no.49, pp.6698-6702, 2014 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 55 Issue: 49
  • Publication Date: 2014
  • Doi Number: 10.1016/j.tetlet.2014.10.044
  • Journal Name: TETRAHEDRON LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.6698-6702
  • Keywords: Pyrrole, Pyrazine, Pyrazinone, Pyrrolopyrazinone, Alkyne cyclization, INHIBITORS, RUPRECHSTYRIL, DESIGN, ESTER, LEAD
  • Middle East Technical University Affiliated: Yes

Abstract

A novel and efficient synthesis of N-substituted pyrrolo-pyrazinone derivatives has been developed. A trichloroacetyl group connected to the pyrrole ring was converted into the desired carboxamide derivatives. Promoted by NaH, the pyrrole carboxamide derivatives underwent a tandem reaction with propargyl bromide to afford pyrrolo-pyrazinones with high efficiency under very mild conditions. The mechanism for the formation of the products is discussed and supported by DFT calculations. (C) 2014 Elsevier Ltd. All rights reserved.