A concise route to pyridines from hydrazides by metal carbene N-H insertion, 1,2,4-triazine formation, and Diels-Alder reaction.
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.
Shi
Baolu
B
School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK.
Lewis
William
W
Campbell
Ian B
IB
Moody
Christopher J
CJ
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
D006834:Hydrazines; D011725:Pyridines; D014227:Triazines; C030011:carbene; D008697:Methane