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

2009/07/29 by Baolu Shi, William Lewis, Ian B. Campbell +1 · 1 citation
Chemistry · #Catalytic C–H Functionalization Methods #Cyclopropane Reaction Mechanisms #Synthesis and Catalytic Reactions

paper · doi:10.1021/ol901502u

openalex publication_date 2009/07/29 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/24

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.

Cited by

• Triazine [wikipedia]