Chemistry of Diazocarbonyl Compounds: XX. Chemoselective O-Alkylation of 3(2H)-Oxoisothiazole-1,1-dioxides

Autor: Lothar Hennig, Liudmila L. Rodina, Bärbel Schulze, Vs. V. Nikolaev, Valerij A. Nikolaev, Jochim Sieler
Rok vydání: 2004
Předmět:
Zdroj: Russian Journal of Organic Chemistry. 40:740-746
ISSN: 1070-4280
DOI: 10.1023/b:rujo.0000043724.25474.51
Popis: Catalytic decomposition of diazoacetylacetone, ethyl diazoacetate, and diethyl diazomalonate effected by dirhodium tetraacetate in the presence of 3(2H)-oxoisothiazole-1,1-dioxides resulted in O-alkylation of amide carbonyl of the heterocycle affording the corresponding enol ethers in preparative yield. The reaction occurred chemoselectively. The 1,3-dicarbonyl derivatives of 3-hydroxyisothiazole-1,1-dioxides obtained in contrast to analogous N-alkylated products are not enolized in solutions and in crystals.
Databáze: OpenAIRE