THE ROUTE OF ALKYLATION OF 5-SUBSTITUTED 1,3,4-THIADIAZOLINE-2-THIONES

Authors

  • Х. Полвонов Al-Khorezmi Urgench State University, Urgench 740000
  • K. Сабиpов Al-Khorezmi Urgench State University, Urgench 740000
  • Х. М. Шахидоятов Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic Uzbekistan, Tashkent 700170

Keywords:

allyl bromide, benzyl chloride, 5-substituted 1,3,4-thiadiazoline-2-thiones, phenoxy-2,3-epoxypropane, S- and N-alkylation, S→N thio-Claisen rearrangement

Abstract

The reaction of 5-anilino(toluidino-, morpholino)-1,3,4-thiadiazoline-2-thiones at 80°C with allyl bromide and benzyl chloride in alcohol, acetonitrile or DMF in the presence of KOH and also with phenoxymethyloxirane in alcohol in the absence of base gives the corresponding novel allyl-, benzyl-, and 2-hydroxy-3-phenoxypropyl products substituted at the exocyclic S atom. Alkylation of the indicated thiones with benzyl chloride at 150-153°C in DMF in the presence of KOH occurs similarly. Under these conditions, allyl bromide forms alkylation products at the endocyclic N(3) atom as a result of an S→N thio-Claisen rearrangement of the initially formed product which is allyl substituted at the exocyclic S atom.

How to Cite
Polvonov, Kh.; Sabirov, Q.; Shakhidoyatov, Kh. M. Chem. Heterocycl. Compd. 2003, 39, 228. [Khim. Geterotsikl. Soedin. 2003, 258.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1023776610073

Published

2003-02-25

Issue

Section

Original Papers