Synthesis of pyrrolo-pyrrolo-pyrazines via the Pd/C-catalyzed cyclization of N-propargyl pyrrolinyl-pyrrole derivatives

Aslanoglu F., Basceken S., BALCI M.

TETRAHEDRON LETTERS, cilt.60, sa.5, ss.449-451, 2019 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 60 Sayı: 5
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1016/j.tetlet.2019.01.004
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.449-451
  • Anahtar Kelimeler: Pyrrole, Bipyrrole, Pyrazine, Dipyrrolopyrazine, Alkyne cyclization, DESIGN
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

A novel and efficient synthesis of N-substituted dipyrrolo[1,2-a:2',1'-c]pyrazine derivatives has been developed. The synthetic strategy relies on the synthesis of 4',5'-dihydro-1H,3'H-2,2'-bipyrrole, followed by the reaction with propargyl bromide. Various substituents were introduced to the alkyne functionality using the Sonogashira coupling reaction. Aromatization of the dihydropyrrole ring followed by an intramolecular cyclization reaction between the alkyne functionality and the pyrrole nitrogen atom was catalyzed by Pd/C at high temperature to furnish the desired dipyrrolo-pyrazine skeleton. (C) 2019 Elsevier Ltd. All rights reserved.