Synthesis of 4-Keto Substituted 1-Alkyl-1,2,3-Triazoles from 5-Substituted 1-Phenyl-l,2,3-Triazole-4-Carbaldehydes

✍ Scribed by Gerrit L'Abbé; Gonda van Essche

• Publisher: Wiley (John Wiley & Sons)
• Year: 2010
• Weight: 118 KB
• Volume: 100
• Category: Article
• ISSN: 0037-9646
• DOI: 10.1002/bscb.19911000402

✦ Synopsis

Triazoles bearing the appropriate substituents at the 4-and 5-positions can rearran-An interesting application was found re-ge thermally via open-chain diazoirnine intermediates. cently in the transformation of l-phenyl-l,2,3-triazole-4-carbaldehyde into l-alkyl-l,2, 3-triazole-4-carbaldehydes through rearrangement of the corresponding imines (see Scheme, R5 = HI.' These findings prompted u s to extend this methodology to the synthesis of 4-ketotriazoles starting from 5-alkyl and 5-aryl substituted 1-phenyl-1 ,2,3-triazole-4-carbaldehydes.