4.8 Article

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

Journal

ORGANIC LETTERS
Volume 11, Issue 16, Pages 3686-3688

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol901502u

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Funding

  1. EPSRC and Glaxo-SmithKline
  2. EPSRC [EP/E018750/1] Funding Source: UKRI
  3. Engineering and Physical Sciences Research Council [EP/E018750/1] Funding Source: researchfish

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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 norbornadlene.

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