☆ 4.5 Article

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

SYNTHESIS-STUTTGART (2011)

Journal

SYNTHESIS-STUTTGART

Volume -, Issue 7, Pages 1037-1044

Publisher

GEORG THIEME VERLAG KG

DOI: 10.1055/s-0030-1258457

Keywords

azides; diazo compounds; diazonium salts; diazo-transfer; heterocycles

Categories

Chemistry, Organic

Funding

Ministry of Education, Culture, Sports, Science, and Technology of Japan [21750105]
Mitsubishi Tanabe Pharma
Grants-in-Aid for Scientific Research [21750105] Funding Source: KAKEN

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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.

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