CYANOACETYLENE AND ITS DERIVATIVES. 29. NEW DATA ON SYNTHESIS AND PROPERTIES OF SUBSTITUTED 1,3-OXATHIOLAN-2-ONES

Authors

  • И. А. Дорофеев Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk 664033
  • А. Г. Малькина Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk 664033
  • Б. А. Трофимов Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk 664033

Keywords:

4-alkyl-4-hydroxy-2-alkynonitriles, 5,5-dialkyl-4-cyanomethylene-1,3-oxathiolan-2-ones, 2 cyanomethyl-4-cyanomethylene-2-[(1-methoxycarbonyloxyethyl-1-methyl)]-5,5-dimethyl-1,3-dithiolane, intramolecular cyclization, hydrolysis, hydrothiocyanation, thiolysis

Abstract

We have determined the conditions for carrying out the reaction of 4-alkyl-4-hydroxy-2-alkynonitriles containing bulky or spirocyclic substituents with the KSCN–KHSO4 system, leading to 5,5-dialkyl-4-cyanomethylene-1,3-oxathiolan-2-ones in quantitative yield (for this, we had to increase the reaction time and use a 10-fold excess of the hydrothiocyanating system compared with the known conditions). 5,5-Dimethyl-4-cyanomethyl-1,3-oxathiolan-2-one reacts with methanol in the presence of triethylamine (20±2°C), forming 2-cyanomethyl-4-cyanomethylene-2-[(1-methoxycarbonyloxyethyl-1-methyl)]-5,5-dimethyl-1,3-dithiolane (yield 90%).

How to Cite
Dorofeev, I. A.; Mal'kina, A. G.; Trofimov, B. A. Chem. Heterocycl. Compd. 2001, 37, 903. [Khim. Geterotsikl. Soedin. 2001, 980.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1012416028013

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Published

2001-07-25

Issue

No. 7 (2001)

Section

Original Papers