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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, Email:

M. Kitamura, N. Tashiro, S. Miyagawa, T. Okauchi, Synthesis, 2011, 1037-1044.

DOI: 10.1055/s-0030-1258457

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2-Azido-1,3-dimethylimidazolinium chloride (ADMC) can be prepared by N-nitrosation of N-aminoguanidine or by the reaction of 2-chloro-1,3-dimethylimidazolinium chloride and sodium azide. The corresponding crystalline phosphate salt (ADMP) is 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.

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2-Azido-1,3-dimethylimidazolinium Chloride: An Efficient Diazo Transfer Reagent for 1,3-Dicarbonyl Compounds

M. Kitamura, N. Tashiro, T. Okauchi, Synlett, 2009, 2931-2934.

Key Words

azides, diazo compounds (esters, ketones), diazonium salts, diazo-transfer, heterocycles

ID: J66-Y2011-0870