specific character of the reaction of derivatives of 2-thioxo-2,3-dihydropyrimidin-4(1H)-one with iodomethane and alkyl chloromethyl sulfides
The alkylation of 5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones with MeI, AllSCH₂Cl, and MeSCH₂Cl in the K₂CO₃-DMF, NaOMe-MeOH, and KOH-EtOH systems was investigated. A hypothetical mechanism for the reaction is examined, and an explanation is proposed for the composition of...
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| Veröffentlicht in: | Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2010-06, Vol.46 (2), p.200-205 |
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| container_title | Chemistry of heterocyclic compounds (New York, N.Y. 1965) |
| container_volume | 46 |
| creator | Novakov, I. A Orlinson, B. S Nawrozkij, M. B Mai, A Artico, M Rotili, D Eremiychuk, A. S Gordeeva, E. A Brunilina, L. L Este, J. A |
| description | The alkylation of 5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones with MeI, AllSCH₂Cl, and MeSCH₂Cl in the K₂CO₃-DMF, NaOMe-MeOH, and KOH-EtOH systems was investigated. A hypothetical mechanism for the reaction is examined, and an explanation is proposed for the composition of the reaction products. The presence of high anti-HIV-1 activity was established in the obtained derivatives of 2-{[(allylsulfanyl)methyl]sulfanyl}pyrimidin-4(3H)-one. |
| doi_str_mv | 10.1007/s10593-010-0492-3 |
| format | Article |
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A ; Orlinson, B. S ; Nawrozkij, M. B ; Mai, A ; Artico, M ; Rotili, D ; Eremiychuk, A. S ; Gordeeva, E. A ; Brunilina, L. L ; Este, J. A</creator><creatorcontrib>Novakov, I. A ; Orlinson, B. S ; Nawrozkij, M. B ; Mai, A ; Artico, M ; Rotili, D ; Eremiychuk, A. S ; Gordeeva, E. A ; Brunilina, L. L ; Este, J. A</creatorcontrib><description>The alkylation of 5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones with MeI, AllSCH₂Cl, and MeSCH₂Cl in the K₂CO₃-DMF, NaOMe-MeOH, and KOH-EtOH systems was investigated. A hypothetical mechanism for the reaction is examined, and an explanation is proposed for the composition of the reaction products. The presence of high anti-HIV-1 activity was established in the obtained derivatives of 2-{[(allylsulfanyl)methyl]sulfanyl}pyrimidin-4(3H)-one.</description><identifier>ISSN: 0009-3122</identifier><identifier>EISSN: 1573-8353</identifier><identifier>DOI: 10.1007/s10593-010-0492-3</identifier><language>eng</language><publisher>Boston: Boston : Springer US</publisher><subject>5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones ; allyl chloro-methyl sulfide ; anti-HIV-1 agents ; Chemistry ; Chemistry and Materials Science ; Dimethylformamide ; methyl chloromethyl sulfide ; methyl iodide ; Organic Chemistry ; Pharmacy ; SN1- and SN2-substitution ; Sulfides</subject><ispartof>Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2010-06, Vol.46 (2), p.200-205</ispartof><rights>Springer Science+Business Media, Inc. 2010</rights><rights>COPYRIGHT 2010 Springer</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c351t-7a7e74eabea184474ba04e20d8fe7fdd7cb85e163e6dc7874fa8d5f4f858b2923</citedby><cites>FETCH-LOGICAL-c351t-7a7e74eabea184474ba04e20d8fe7fdd7cb85e163e6dc7874fa8d5f4f858b2923</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s10593-010-0492-3$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s10593-010-0492-3$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27903,27904,41467,42536,51297</link.rule.ids></links><search><creatorcontrib>Novakov, I. A</creatorcontrib><creatorcontrib>Orlinson, B. S</creatorcontrib><creatorcontrib>Nawrozkij, M. B</creatorcontrib><creatorcontrib>Mai, A</creatorcontrib><creatorcontrib>Artico, M</creatorcontrib><creatorcontrib>Rotili, D</creatorcontrib><creatorcontrib>Eremiychuk, A. S</creatorcontrib><creatorcontrib>Gordeeva, E. A</creatorcontrib><creatorcontrib>Brunilina, L. L</creatorcontrib><creatorcontrib>Este, J. A</creatorcontrib><title>specific character of the reaction of derivatives of 2-thioxo-2,3-dihydropyrimidin-4(1H)-one with iodomethane and alkyl chloromethyl sulfides</title><title>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</title><addtitle>Chem Heterocycl Comp</addtitle><description>The alkylation of 5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones with MeI, AllSCH₂Cl, and MeSCH₂Cl in the K₂CO₃-DMF, NaOMe-MeOH, and KOH-EtOH systems was investigated. A hypothetical mechanism for the reaction is examined, and an explanation is proposed for the composition of the reaction products. The presence of high anti-HIV-1 activity was established in the obtained derivatives of 2-{[(allylsulfanyl)methyl]sulfanyl}pyrimidin-4(3H)-one.</description><subject>5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones</subject><subject>allyl chloro-methyl sulfide</subject><subject>anti-HIV-1 agents</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Dimethylformamide</subject><subject>methyl chloromethyl sulfide</subject><subject>methyl iodide</subject><subject>Organic Chemistry</subject><subject>Pharmacy</subject><subject>SN1- and SN2-substitution</subject><subject>Sulfides</subject><issn>0009-3122</issn><issn>1573-8353</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNp9kc1uEzEUhS1EJULKA7BiliDh1r-xZ1lVQCtVYgFdW459nbllMo7saUseou-Mw7BGXljfkY-vjw8h7zm74IyZy8qZ7iVlnFGmekHlK7Li2khqpZavyYox1lPJhXhD3tb60NBwq1bkpR4gYMLQhcEXH2YoXU7dPEBXoCHm6cQRCj75GZ-gnlDQecD8O1PxWdKIwzGWfDgW3GPEiaqP_OYTzRN0zzgPHeaY9zAPvgl-ip0ffx3HNm7M5a_eoD6OCSPUc3KW_Fjh3b99Te6_fvl5fUPvvn-7vb66o0FqPlPjDRgFfgu-hVBGbT1TIFi0CUyK0YSt1cA3EjYxGGtU8jbqpJLVdit6IdfkYrl350dwOKU8t-xtRdhjaC9P2PQrqQ2TSrdvXBO-GELJtRZI7tDS-nJ0nLlTAW4pwLUC3KkAJ5tHLJ7azk47KO4hP5ap5fqv6cNiSj47vytY3f0Pwbhk3G6EUL38A6CjlEQ</recordid><startdate>20100601</startdate><enddate>20100601</enddate><creator>Novakov, I. A</creator><creator>Orlinson, B. S</creator><creator>Nawrozkij, M. B</creator><creator>Mai, A</creator><creator>Artico, M</creator><creator>Rotili, D</creator><creator>Eremiychuk, A. S</creator><creator>Gordeeva, E. A</creator><creator>Brunilina, L. L</creator><creator>Este, J. A</creator><general>Boston : Springer US</general><general>Springer US</general><general>Springer</general><scope>FBQ</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20100601</creationdate><title>specific character of the reaction of derivatives of 2-thioxo-2,3-dihydropyrimidin-4(1H)-one with iodomethane and alkyl chloromethyl sulfides</title><author>Novakov, I. A ; Orlinson, B. S ; Nawrozkij, M. B ; Mai, A ; Artico, M ; Rotili, D ; Eremiychuk, A. S ; Gordeeva, E. A ; Brunilina, L. L ; Este, J. 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A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>specific character of the reaction of derivatives of 2-thioxo-2,3-dihydropyrimidin-4(1H)-one with iodomethane and alkyl chloromethyl sulfides</atitle><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle><stitle>Chem Heterocycl Comp</stitle><date>2010-06-01</date><risdate>2010</risdate><volume>46</volume><issue>2</issue><spage>200</spage><epage>205</epage><pages>200-205</pages><issn>0009-3122</issn><eissn>1573-8353</eissn><abstract>The alkylation of 5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones with MeI, AllSCH₂Cl, and MeSCH₂Cl in the K₂CO₃-DMF, NaOMe-MeOH, and KOH-EtOH systems was investigated. A hypothetical mechanism for the reaction is examined, and an explanation is proposed for the composition of the reaction products. The presence of high anti-HIV-1 activity was established in the obtained derivatives of 2-{[(allylsulfanyl)methyl]sulfanyl}pyrimidin-4(3H)-one.</abstract><cop>Boston</cop><pub>Boston : Springer US</pub><doi>10.1007/s10593-010-0492-3</doi><tpages>6</tpages></addata></record> |
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| identifier | ISSN: 0009-3122 |
| ispartof | Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2010-06, Vol.46 (2), p.200-205 |
| issn | 0009-3122 1573-8353 |
| language | eng |
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| subjects | 5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones allyl chloro-methyl sulfide anti-HIV-1 agents Chemistry Chemistry and Materials Science Dimethylformamide methyl chloromethyl sulfide methyl iodide Organic Chemistry Pharmacy SN1- and SN2-substitution Sulfides |
| title | specific character of the reaction of derivatives of 2-thioxo-2,3-dihydropyrimidin-4(1H)-one with iodomethane and alkyl chloromethyl sulfides |
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