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

Cetinkaya Y., BALCI M.

TETRAHEDRON LETTERS, cilt.55, sa.49, ss.6698-6702, 2014 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 55 Sayı: 49
  • Basım Tarihi: 2014
  • Doi Numarası: 10.1016/j.tetlet.2014.10.044
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.6698-6702
  • Anahtar Kelimeler: Pyrrole, Pyrazine, Pyrazinone, Pyrrolopyrazinone, Alkyne cyclization, INHIBITORS, RUPRECHSTYRIL, DESIGN, ESTER, LEAD
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

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.