2012
DOI: 10.1155/2013/176213
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Synthesis of 2,3‐Dihydro‐6‐methyl‐2‐thiopyrimidin‐4(1H)‐one (6‐Methylthiouracil) Derivatives and Their Reactions

Abstract: 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 ac… Show more

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Cited by 5 publications
(6 citation statements)
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“…Reaction of thiouracil derivatives with halogenated compounds in basic medium to produce S-alkylated derivatives was reported [41] , [42] . On the basics of this previously reported reactions; thiouracil derivatives 3a-d were successfully alkylated with chloroacetic acid in the presence of sodium hydroxide to afford sulfanyl acetic acid derivatives 5a-d .…”
Section: Resultsmentioning
confidence: 99%
“…Reaction of thiouracil derivatives with halogenated compounds in basic medium to produce S-alkylated derivatives was reported [41] , [42] . On the basics of this previously reported reactions; thiouracil derivatives 3a-d were successfully alkylated with chloroacetic acid in the presence of sodium hydroxide to afford sulfanyl acetic acid derivatives 5a-d .…”
Section: Resultsmentioning
confidence: 99%
“…Synthesis of the starting 6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one 1 was carried out according to the known method (Barmaki et al 2013) by condensation of ethyl acetoacetate with thiourea in methanol. The next modification was carried out in several directions.…”
Section: Resultsmentioning
confidence: 99%
“…6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one(1) obtained by the method described in the literature (Barmaki et al 2013).…”
Section: Chemistrymentioning
confidence: 99%
“…This started with a typical cyclocondensation reaction of thiourea with esters 2a-c and malononitrile 2d using sodium ethoxide under refluxing conditions. [30][31][32][33] The reaction of thiourea with acetophenone derivatives 4a-d and molecular iodine resulted in the formation of 2-amino-thiazoles 5a-d, [34] which were then reacted with chloroacetyl chloride in the presence of triethylamine to produce 2-chloroacylaminothiazoles 6a-d. [35] Following the next step, S-alkylation of thiouracil\thiocytosine derivatives 3a-d with chloroacyl-aminothiazoles 6a-d using anhydrous K 2 CO 3 at 80°C yielded our desirable first set of 1,6-dihydropyrimidine derivatives 7a-l.…”
Section: Chemistrymentioning
confidence: 99%
“…( and analytical data of compounds 3a-d, [30][31][32][33] 5a-d, [34] and 6a-d [35] are given as reported.…”
Section: Structure-activity Relationship (Sar) Analysismentioning
confidence: 99%