Highly regioselective one-step synthesis of 1-benzyl-5-formyl-1,2,3-triazole-4-carboxylates

Erdemir G., Altundaş A.

Chemistry of Heterocyclic Compounds, cilt.59, sa.4-5, ss.267-276, 2023 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 59 Sayı: 4-5
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1007/s10593-023-03192-0
  • Dergi Adı: Chemistry of Heterocyclic Compounds
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Index Chemicus (IC), Current Chemical Reactions (CCR)
  • Sayfa Sayıları: ss.267-276
  • Anahtar Kelimeler: 1,2,3-triazole, aldehyde, reduction, regioselective, tri-tert-butoxyaluminum hydride
  • Gazi Üniversitesi Adresli: Evet

Özet

[Figure not available: see fulltext.] A novel methodology has been developed to afford 1,4,5-trisubstituted 1-benzyl-5-formyl-1,2,3-triazole-4-carboxylates in one step under mild conditions. This method includes the reduction of the ester functional group to an aldehyde using lithium tri-tert-butoxyaluminum hydride. Especially, this method offers a different perspective for fully substituted 1,2,3-triazoles with high regioselectivity and high yields. The structure of fully substituted triazoles was verified using FTIR, 1H, 13C NMR spectroscopy, HRMS, advanced NMR techniques (COSY, C-APT, HSQC, and HMBC), and X-ray crystallography.