title: Rapid Access to 3-Aminoindazoles from Tertiary Amides.
abstract: A two-step synthesis of structurally diverse 3-aminoindazoles from readily available starting materials was developed. This sequence includes a one-pot synthesis of aminohydrazones through chemoselective Tf2O-mediated activation of tertiary amides and subsequent addition of nucleophilic hydrazides. These precursors then participate in an intramolecular ligand-free Pd-catalyzed C-H amination reaction. The azaheterocycles synthesized via this approach were further diversified through subsequent deprotection/functionalization reactions.
authors.affiliation: Centre in Green Chemistry and Catalysis, Department of Chemistry, Faculty of Arts and Science, Université de Montréal, Station Downtown, Québec H3C 3J7, Canada.
authors.forename: Patrick
authors.initials: P
authors.lastname: Cyr
authors.affiliation: Centre in Green Chemistry and Catalysis, Department of Chemistry, Faculty of Arts and Science, Université de Montréal, Station Downtown, Québec H3C 3J7, Canada.
authors.forename: Sophie
authors.initials: S
authors.lastname: Régnier
authors.affiliation: Centre in Green Chemistry and Catalysis, Department of Chemistry, Faculty of Arts and Science, Université de Montréal, Station Downtown, Québec H3C 3J7, Canada.
authors.forename: William S
authors.initials: WS
authors.lastname: Bechara
authors.affiliation: Centre in Green Chemistry and Catalysis, Department of Chemistry, Faculty of Arts and Science, Université de Montréal, Station Downtown, Québec H3C 3J7, Canada.
authors.forename: André B
authors.initials: AB
authors.lastname: Charette
mesh_terms: D000577:Amides / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006835:Hydrazones / Q000138:chemical synthesis* / Q000737:chemistry; D007191:Indazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry
chemical_list: D000577:Amides; D000588:Amines; D006835:Hydrazones; D007191:Indazoles; D010165:Palladium