Synthesis of Benz-Fused Azoles via C‑Heteroatom Coupling Reactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands

• Published in: ACS combinatorial science Vol. 21; no. 5; pp. 389 - 399
• Main Authors: Mishra, Nidhi, Singh, Anoop S, Agrahari, Anand K, Singh, Sumit K, Singh, Mala, Tiwari, Vinod K
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 13.05.2019; Amer Chemical Soc
• Subjects: Azides - chemistry; Azoles - chemical synthesis; Catalysis; Chemistry; Chemistry, Applied; Chemistry, Medicinal; Chemistry, Multidisciplinary; Copper - chemistry; Glycosylation; Life Sciences & Biomedicine; Ligands; Molecular Structure; Pharmacology & Pharmacy; Physical Sciences; Quinazolinones - chemistry; Science & Technology; Triazoles - chemistry; cross-coupling; glycosyl triazole; catalysis; click chemistry; benzazole; ligand; ESTER; O-ARYLATION; DOMINO SYNTHESIS; EFFICIENT METHOD; FACILE SYNTHESIS; ARYL HALIDES; BENZOXAZOLES; INHIBITORS; BENZOTHIAZOLES; CYCLIZATION
• ISSN: 2156-8952; 2156-8944; 2156-8944
• DOI: 10.1021/acscombsci.9b00004

Glycosyl triazoles are conveniently accessible and contain multiple metal-binding units that may assist in metal-mediated catalysis. Azide derivatives of d-glucose have been converted to their respective aryltriazoles and screened as ligands for the synthesis of 2-substituted benz-fused azoles and benzimidazoquinazolinones by Cu-catalyzed intramolecular Ullmann type C-heteroatom coupling. Good to excellent yields for a variety of benz-fused heterocyles were obtained for this readily accessible catalytic system.