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DOI: 10.1055/s-0030-1258457
2-Azido-1,3-dimethylimidazolinium Salts: Efficient Diazo-Transfer Reagents for 1,3-Dicarbonyl Compounds
Publication History
Publication Date:
02 March 2011 (online)
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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
The prepared hydrochloride salt of 4 was very hygroscopic. The amount of HCl in the salt was estimated to be 2 by elemental analysis (see the experimental section).
14Initially, methanol was added as a co-solvent to dissolve sodium azide in the reaction mixture; however, its use did not increase the yields of diazotized compounds.
16Recently, we reported the preparation of ADMP (3b) and its diazo-transfer to primary amines as a communication (see ref. 11a).
18Impact sensitivity was determined to be >25 [Nm] by the German Federal Institute for Materials Research and Testing (BAM) procedure.
19Friction sensitivity was determined to be >360 [N] by the German Federal Institute for Materials Research and Testing (BAM) procedure.