4,5-DIALKYL-SUBSTITUTED 3-OXO-(2H)-ISOTHIAZOLE 1,1-DIOXIDES IN REACTIONS WITH DIAZOMETHANE

Authors

  • Л. Л. Родина Saint Petersburg State University, Saint Petersburg 198504
  • Д. Б. Гидон Saint Petersburg State University, Saint Petersburg 198504
  • Вс. В. Николаев Saint Petersburg State University, Saint Petersburg 198504
  • Б. Шульце Institute of Organic Chemistry, Leipzig University, Leipzig 04103

DOI:

https://doi.org/10.1007/7027

Keywords:

diazomethane, 4, 5-dialkyl-3-oxo-(2H)-isothiazole 1, 1-dioxides, isothiazolopyrazolines, methylation, 1, 3-cycloaddition

Abstract

It has been established that the interaction of  diazomethane with 4,5-dialkyl-substituted 3-oxo-(2H)-isothiazole 1,1-dioxides proceeds in two stages. Initially alkylation of the sulfonimide nitrogen atom and the carbonyl group oxygen atom occurs (in a ratio of ~ 3:2), then there is a regioselective cycloaddition of diazomethane at the C=C double bond with the formation of the corresponding N-methyloxoisothiazolopyrazolines and 3-methoxyisothiazolopyrazolines.

How to Cite
Rodina, L. L.; Gidon, D. B.; Nikolaev, Vs. V.; Shulze, B.  Chem. Heterocycl. Compd. 2008, 44, 466. [Khim. Geterotsikl. Soedin. 2008, 595.]

For this article in the English edition see DOI 10.1007/s10593-008-0065-x

 


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Published

2022-09-01

Issue

No. 4 (2008)

Section

Original Papers