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.
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Alexander R. Pelley
Salman Bagherzadeh
Jianbin Lin
The Journal of Organic Chemistry
Memorial University of Newfoundland
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Pelley et al. (Fri,) studied this question.
www.synapsesocial.com/papers/6980feabc1c9540dea810efe — DOI: https://doi.org/10.1021/acs.joc.5c02682