Abstract
We have developed the diazo-transfer of 2-azido-1,3-dimethylimidazolinium
salts to 1,3-dicarbonyl compounds. 2-Azido-1,3-dimethylimidazolinium
chloride (ADMC) was prepared by N-nitrosation
of N-aminoguanidine or by the reaction
of 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and sodium
azide. The corresponding phosphate, ADMP, was isolated as a crystal,
and was found to be a stable and safe reagent. Both ADMC and ADMP
reacted with 1,3-dicarbonyl compounds under mild conditions to give 2-diazo-1,3-dicarbonyl
compounds in high yields, which are easily isolated because the
by-products are highly soluble in water.
Key words
azides - diazo compounds - diazonium salts - diazo-transfer - heterocycles
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