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: kitache.kyutech.ac.jp
M. Kitamura, N. Tashiro, S. Miyagawa, T. Okauchi, Synthesis, 2011, 1037-1044.
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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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M. Kitamura, N. Tashiro, T. Okauchi, Synlett, 2009, 2931-2934.