2-Azido-1,3-dimethylimidazolinium
Salts: Efficient Diazo-Transfer Reagents for 1,3-Dicarbonyl Compounds

Mitsuru Kitamura; Norifumi Tashiro; Satoshi Miyagawa; Tatsuo Okauchi

doi:10.1055/s-0030-1258457

PAPER

2-Azido-1,3-dimethylimidazolinium Salts: Efficient Diazo-Transfer Reagents for 1,3-Dicarbonyl Compounds

Mitsuru Kitamura*, Norifumi Tashiro, Satoshi Miyagawa, Tatsuo Okauchi
Department of Applied Chemistry, Kyushu Institute of Technology, 1-1 Sensuicho, Tobata, Kitakyushu, 804-8550, Japan
Fax: +81(93)8843304; e-Mail: kita@che.kyutech.ac.jp;

Abstract

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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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References

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