A concise route to pyridines from hydrazides by metal carbene N-H insertion, 1,2,4-triazine formation, and Diels-Alder reaction

Baolu Shi; William Lewis; Ian B Campbell; Christopher J Moody

doi:10.1021/ol901502u

A concise route to pyridines from hydrazides by metal carbene N-H insertion, 1,2,4-triazine formation, and Diels-Alder reaction

Org Lett. 2009 Aug 20;11(16):3686-8. doi: 10.1021/ol901502u.

Authors

Baolu Shi¹, William Lewis, Ian B Campbell, Christopher J Moody

Affiliation

¹ School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK.

PMID: 19719202
DOI: 10.1021/ol901502u

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Cyclization
Hydrazines / chemistry*
Methane / analogs & derivatives
Methane / chemistry
Molecular Structure
Pyridines / chemical synthesis*
Pyridines / chemistry
Triazines / chemical synthesis*
Triazines / chemistry

Substances

Hydrazines
Pyridines
Triazines
carbene
Methane