title: A concise route to pyridines from hydrazides by metal carbene N-H insertion, 1,2,4-triazine formation, and Diels-Alder reaction.
abstract: A simple, new three-step sequence for the conversion of hydrazides into pyridines is reported in which the key steps are N-H insertion by a copper carbene intermediate derived from alpha-diazo-beta-ketoesters into the hydrazide, reaction with ammonium acetate to give 1,2,4-triazines, followed by Diels-Alder reaction with norbornadiene.
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK.
authors.forename: Baolu
authors.initials: B
authors.lastname: Shi
authors.forename: William
authors.initials: W
authors.lastname: Lewis
authors.forename: Ian B
authors.initials: IB
authors.lastname: Campbell
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Moody
mesh_terms: D002384:Catalysis; D003500:Cyclization; D006834:Hydrazines / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D014227:Triazines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006834:Hydrazines; D011725:Pyridines; D014227:Triazines; C030011:carbene; D008697:Methane