Synthesis of α,β-Unsaturated Diazoketones through the Use of N , N ′-Ditosylhydrazine
Abstract
A scalable synthesis of α,β-unsaturated diazoketones has been developed through the reaction of 1-iodoenones with N, N ′-ditosylhydrazine. 1-Chloroenones, accessible from aldehydes via a Wittig-type homologation, undergo in situ halide exchange and diazo transfer in a one-pot sequence that minimizes purification and enhances efficiency. This strategy offers practical access to α,β-unsaturated diazoketones, which serve as versatile intermediates for synthesis and reaction discovery. In addition, selective formation of dihydropyridazinones through a 1,4-addition pathway is described.
Fields of Study & Subjects
Cyclopropane Reaction Mechanisms
Organic Chemistry Synthesis Methods
Synthesis of heterocyclic compounds
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Volume
- 91
- Issue
- 6
- Pages
- 2626–2631
- Publication date
- 30 January 2026
- Language
- EN