American Chemical Society
ol901502u_si_001.pdf (1.27 MB)

A Concise Route to Pyridines from Hydrazides by Metal Carbene N−H Insertion, 1,2,4-Triazine Formation, and Diels−Alder Reaction

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journal contribution
posted on 2009-08-20, 00:00 authored by Baolu Shi, William Lewis, Ian B. Campbell, Christopher J. Moody
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 α-diazo-β-ketoesters into the hydrazide, reaction with ammonium acetate to give 1,2,4-triazines, followed by Diels−Alder reaction with norbornadiene.