"Metal-free" synthesis of 1, 2, 3-triazoles via tandem azidation, intramolecular [3+2]-cycloaddition and aromatization of ethyl acrylate derivatives. Issue 24 (13th June 2018)

• Record Type: Journal Article
• Authors: Kumar, B. Senthil; Gadakh, Sunita; Sudalai, Arumugam
• Is Part Of: Tetrahedron letters. Volume 59:Issue 24(2018)
• Page Start: 2365
• Page End: 2367
• Publication Date: 2018-06-13
• Subjects: Tandem azidation -- Intramolecular cycloaddition -- Regioselective -- Triazoles; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.05.020
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Single step, high yield synthesis of 1, 2, 3-triazoles. α, β-unsaturated esters have been used as substrates. Azide had been added across CC bond intramolecularly under cycloaddition mode. "Metal free" synthesis. High regio and distereoselectivity. Abstract: An efficient "one-pot" method for the synthesis of substituted 1, 2, 3-triazole derivatives in excellent yields as single regioisomer is reported. The key transformation involves an atom-efficient tandem azidation, intramolecular [3+2]-cycloaddition and aromatization of acrylate derivatives on treatment with NaN3 in DMF under mild conditions.