Abstract
2-Azido-1,3-dimethylimidazolinium chloride (ADMC) and its corresponding hexafluorophosphate (ADMP) were found to be safe and efficient diazo-transfer reagents to various organic compounds. ADMC was prepared by the reaction of 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and sodium azide. ADMP was isolated as a crystal having thermal stability and low explosibility. ADMC and ADMP reacted with 1,3-dicarbonyl compounds under mild basic 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. Naphthols also reacted with ADMC to give corresponding diazonaphthoquinones in good to high yields. Furthermore, ADMP shows efficient diazo-transfer ability to primary amines even without the aid of a metal salt such as Cu(II). Using this diazotization approach, various alkyl/aryl azides were obtained directly from corresponding primary amines in high yields. In addition, ADMC/ADMP could be used as azide-transfer and amidation reagents.
