Design of Pyrazolo-pyrrolo-pyrazines and Pyrazolo-pyrrolo-diazepines via AuCl3-Catalyzed and NaH-Supported Cyclization of N-Propargyl Pyrazoles

Basceken S., BALCI M.

JOURNAL OF ORGANIC CHEMISTRY, cilt.80, sa.8, ss.3806-3814, 2015 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 80 Sayı: 8
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1021/acs.joc.5b00034
  • Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.3806-3814
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

A concise synthetic methodology for new heterocyclic scaffolds, such as pyrazolo-pyrrolo-pyrazine and pyrazolo-pyrrolo-diazepine skeletons, was developed. The key features of this method include (i) synthesis of pyrrole-derived alpha,beta-alkynyl ketones, (ii) introduction of various substituents into the alkyne functionality by Sonogashira cross-coupling, (iii) synthesis of pyrazole units by the reaction of alpha,beta-alkynyl compounds with hydrazine monohydrate, (iv) gold-catalyzed cyclization of pyrazoles with alkyne units, and (v) cyclization with NaH. Furthermore, this methodology allows various substituents to be introduced into all positions of the target compounds.