Cu(I)-catalyzed alkyne-azide "click' cycloaddition (CuAAC): a clean, efficient, and mild synthesis of new 1,4-disubstituted 1H-1,2,3-triazole-linked 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile-crystal structure

Aghbash K. O., Pesyan N. N., ŞAHİN E.

RESEARCH ON CHEMICAL INTERMEDIATES, cilt.45, sa.4, ss.2079-2094, 2019 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 45 Sayı: 4
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1007/s11164-018-03723-x
  • Dergi Adı: RESEARCH ON CHEMICAL INTERMEDIATES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2079-2094
  • Anahtar Kelimeler: 4H-pyrans, 2-Amino-6-(azidomethyl)-4, 8-dihydropyrano[3, 2-b]pyran-3-carbonitrile, Azide-alkyne 1, 3-dipolar cycloaddition, Click reaction, Copper catalysis, 1,2,3-Triazoles, Dimeric form, Co-crystal, THROUGHPUT SCREENING ASSAY, ONE-POT SYNTHESIS, APOPTOSIS INDUCERS, ANTIBACTERIAL ACTIVITY, 1,2,3-TRIAZOLE DERIVATIVES, GREEN SYNTHESIS, DISCOVERY, SERIES, 4-ARYL-4H-CHROMENES, CHEMISTRY
  • Atatürk Üniversitesi Adresli: Evet

Özet

Cu(I)-catalyzed alkyne-azide click' cycloaddition (CuAAC) is an important click chemistry'' reaction that is widely known in materials science, chemical biology, and pharmaceutical chemistry. The CuAAC reaction of terminal alkynes affords an efficient and mild production of triazolic 1,4-disubstituted compounds. In this work, a green and valuable method was introduced for the synthesis of the category of different new 1,4-disubstituted 1,2,3-triazole swapped with a 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-cyano moiety. These triazolic derivatives were produced by treatment of various 2-amino-6-(azidomethyl)-4,8-dihydropyrano[3,2-b]pyran-3-carbonitriles with phenylacetylene in the presence of CuI as a catalyst with excellent yields (because CuAAC is selective to 1,4-disubstituted triazole derivatives) in a green solvent (ethanol/water). All structures were evaluated by C-13, H-1 NMR, and FT-IR spectroscopy and a compound was analyzed by crystallography (X-ray) technique.