Facile Entry into Triazole Fused Heterocycles via Sulfamidate Derived Azido-alkynes

• Published in: Journal of organic chemistry 2009-10, Vol.74 (19), p.7588-7591
• Main Authors: Sai Sudhir, V, Phani Kumar, N. Y, Nasir Baig, R. B, Chandrasekaran, Srinivasan
• Format: Article
• Language: English
• Subjects: Alkynes - chemistry; Azides - chemistry; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Cyclization; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Molecular Conformation; Organic chemistry; Preparations and properties; Stereoisomerism; Sulfonic Acids - chemistry; Triazoles - chemical synthesis; Triazoles - chemistry
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo9016748

Direct synthesis of condensed triazoles from diverse sulfamidates by ring opening of sulfamidates with sodium azide followed by one-pot propargylation and cycloaddition furnished title compounds. The methodology in general has been demonstrated on diverse sulfamidates derived from amino acids, amino acid derivatives, and carbohydrates to obtain diverse triazole fused scaffolds. In one example, a condensed triazole containing amino acid has been synthesized by ring opening of a sulfamidate derivative with propargyl amine.