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Synthesis of 2,3-dihydro-6-methyl-2-thiopyrimidin-4(1 H)-one (6-methylthiouracil) derivatives and their reactions
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نویسنده
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barmaki m. ,valiyeva g. ,maharramovm a.a. ,allaverdiyev m.m.
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منبع
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journal of chemistry - 2013 - دوره : 2013 - شماره : 0
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چکیده
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The synthesis and characterization of 2,3-dihydro-6-methyl-2- thioxopyrimidin-(1h)-one (i) and some of its derivatives has been performed in our lab. ring-closing cyclization,as a result of the condensation of ethyl-3-oxobutanoate with thiourea in koh in an ethanol medium produced 2,3-dihydro-6-methy -2-thioxopyrimidin-(1h)-one (i). the reaction of compound (i) with 2- chloroacetic acid in an alkaline koh solution produced the carboxylate derivative,2-(2,6-dihydro-4-methyl-6-oxopyrimidin-2-yl-thio) ethanoic acid (ii). the reaction of the resulted derivative of carboxylate (ii) with the salt of copper sulphate,produced a new copper salt (iii). a substitution reaction between synthesized compound (i) and 2-chloroethanol in an aqueous solution of koh,created 2-(2-hydroxyethylthio)-6-methylpyrimidin-4(3h) -one (iv). the reaction of compound (i) with 2-(chloromethyl)oxirane in the presence of an aqueous solution of koh,resulted yielded 2-(3-chloro-2-hydroxy- propylthio)-6-methylpyrimidin-4(3h)-one (v). sodium mercaptide compound (vi),was produced by the reaction of (i) with naoh and then the sodium salt of 2,3-dihydro-6-methyl-2-thioxopyrimidin-(1h)-one (vi) was reacted with 2-(chloromethyl)oxirane to result in 2-((oxiran-2-yl) methyl-thio)-6-methyl- pyrimidin-4(3h)-one (vii). different acylation reagents (acetyl chloride,benzoyl chloride) were reacted with compound (i),in dimethylformamide,acylation happens on sulfur and furnished s-acylified derivatives of (viii-ix). all the synthesized and obtained products were confirmed by ir,1h,and 13c nmr and elemental analysis. © 2013 mohammad barmaki et al.
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آدرس
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faculty of chemistry,north tehran branch,islamic azad university, ایران, department of chemistry,baku state university, Azerbaijan, department of chemistry,baku state university, Azerbaijan, department of chemistry,baku state university, Azerbaijan
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Authors
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