title: A step-economical route to fused 1,2,3-triazoles via an intramolecular 1,3-dipolar cycloaddition between a nitrile and an in situ generated aryldiazomethane.
abstract: An intramolecular 1,3-dipolar cycloaddition strategy for rapid entry into triazole-fused heterocyclic compounds without recourse to the traditional Cu(1)-catalyzed azide-alkyne cycloadditions is described. Central to the strategy is the in situ generation of substituted diazomethanes in a two-step sequence from the corresponding aldehydes, which then undergo smooth cycloaddition with a cyano group to generate the desired fused 1,2,3-triazoles in good overall yields. The entire sequence can be carried out in a one-pot operation.
authors.affiliation: Janssen Research & Development, LLC , 3210 Merryfield Row, San Diego, California 92121, United States.
authors.forename: Neelakandha S
authors.initials: NS
authors.lastname: Mani
authors.forename: Anne E
authors.initials: AE
authors.lastname: Fitzgerald
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D061565:Cycloaddition Reaction; D003978:Diazomethane / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000480:Alkynes; D006571:Heterocyclic Compounds; D009570:Nitriles; D014230:Triazoles; D003978:Diazomethane; D003300:Copper