Transition-Metal-Free Synthesis of 4-Alkynylquinazolines

UÇAR S., DAŞTAN A.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, cilt.2022, sa.13, 2022 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 2022 Sayı: 13
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1002/ejoc.202200131
  • Dergi Adı: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Applied Science & Technology Source, CAB Abstracts, Chimica
  • Anahtar Kelimeler: Alkynylation, Aromatic substitution, C-C coupling, Ring opening, Synthetic methods, QUINAZOLINE, SERIES, CONSTRUCTION, CYCLIZATION, CONVENIENT
  • Atatürk Üniversitesi Adresli: Evet

Özet

Protocols have been developed that allow easy access to 4-alkynylquinazolines under transition-metal-free conditions. The ring opening reaction of 4-(benzofuran-2-yl)quinazolines obtained from the arylation of quinazolines with benzofuran is the first way to achieve 4-alkynylquinazolines. Direct alkynylation of quinazolines with terminal alkynes in the presence of n-BuLi and iodine or with alkynyl Grignard reagents is another strategy. Desilylation of 4-((trimethylsilyl)ethynyl)quinazolines obtained by direct alkynation is the third approach to give 4-alkynylquinazolines. It has also been shown that the protocols are applicable for scale-up synthesis.