The Route of Alkylation of 5-Substituted 1,3,4-Thiadiazoline-2-thiones |
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Authors: | Kh Polvonov Q Sabirov Kh M Shakhidoyatov |
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Institution: | (1) Al-Khorezmi Urgench State University, Urgench, 740000, Uzbekistan;(2) Academy of Sciences of the Republic Uzbekistan, Institute of the Chemistry of Plant Substances, Tashkent, 700170 |
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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. |
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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" target="_blank">gif" alt="rarr" align="BASELINE" BORDER="0">N thio-Claisen rearrangement |
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