3-Diazopropene alkylates 3-cyanocoumarin, giving 4-allyl-3-cyanocoumarin. The pyrazole formed by isomerisation of 3-diazopropene slowly adds to 4-allyl-3-cyanocoumarin, giving 3-cyano-4-[2-methyl-2-(pyrazol-1-yl)-ethyl]coumarin (III), this addition being catalysed by 3-diazopropene acting as a nitrogen base.
R. Clinging and F. M. Dean, J. Chem. Soc. C, 1971, 3668 DOI: 10.1039/J39710003668
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