A new improved method for the synthesis of 2,4-diarylpyrimidines starting from 2,2,2-trichloroethylideneacetophenones
An advantageous new approach to 2,4-diarylpyrimidines has been developed. 2,2,2-Trichloroethylideneacetophenones reacted with benzamidines leading to novel 2,6-diaryl-6-hydroxy-4-trichloromethyl-1,4,5,6-tetrahydropyrimidines in near quantitative yields. These compounds were efficiently dehydrated to...
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| Veröffentlicht in: | Tetrahedron letters 2013-09, Vol.54 (37), p.5115-5117 |
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| creator | Guirado, Antonio Alarcón, Enrique Vicente, Yesica Andreu, Raquel |
| description | An advantageous new approach to 2,4-diarylpyrimidines has been developed. 2,2,2-Trichloroethylideneacetophenones reacted with benzamidines leading to novel 2,6-diaryl-6-hydroxy-4-trichloromethyl-1,4,5,6-tetrahydropyrimidines in near quantitative yields. These compounds were efficiently dehydrated to obtain previously unknown 2,4-diaryl-6-trichloromethyl-1,6-dihydropyrimidines, which were able to undergo aromatisation via chloroform elimination to give 2,4-diarylpyrimidines in high yields. A main improvement of this procedure lies in circumventing the oxidative dehydrogenation of dihydropyrimidine intermediates. This preparative process has also been adapted to a one-pot protocol. |
| doi_str_mv | 10.1016/j.tetlet.2013.07.075 |
| format | Article |
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These compounds were efficiently dehydrated to obtain previously unknown 2,4-diaryl-6-trichloromethyl-1,6-dihydropyrimidines, which were able to undergo aromatisation via chloroform elimination to give 2,4-diarylpyrimidines in high yields. A main improvement of this procedure lies in circumventing the oxidative dehydrogenation of dihydropyrimidine intermediates. This preparative process has also been adapted to a one-pot protocol.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2013.07.075</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Benzamidines ; Chloral ; Chloroform ; Dehydration ; Dehydrogenation ; Pyrimidines ; Synthesis (chemistry) ; Tetrahedrons ; Trichloroethylideneacetophenones</subject><ispartof>Tetrahedron letters, 2013-09, Vol.54 (37), p.5115-5117</ispartof><rights>2013 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c339t-7e604b9d6274e3156109afd8bf83654a29904d870a2ecba52b5a650a2f6547113</citedby><cites>FETCH-LOGICAL-c339t-7e604b9d6274e3156109afd8bf83654a29904d870a2ecba52b5a650a2f6547113</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tetlet.2013.07.075$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids></links><search><creatorcontrib>Guirado, Antonio</creatorcontrib><creatorcontrib>Alarcón, Enrique</creatorcontrib><creatorcontrib>Vicente, Yesica</creatorcontrib><creatorcontrib>Andreu, Raquel</creatorcontrib><title>A new improved method for the synthesis of 2,4-diarylpyrimidines starting from 2,2,2-trichloroethylideneacetophenones</title><title>Tetrahedron letters</title><description>An advantageous new approach to 2,4-diarylpyrimidines has been developed. 2,2,2-Trichloroethylideneacetophenones reacted with benzamidines leading to novel 2,6-diaryl-6-hydroxy-4-trichloromethyl-1,4,5,6-tetrahydropyrimidines in near quantitative yields. These compounds were efficiently dehydrated to obtain previously unknown 2,4-diaryl-6-trichloromethyl-1,6-dihydropyrimidines, which were able to undergo aromatisation via chloroform elimination to give 2,4-diarylpyrimidines in high yields. A main improvement of this procedure lies in circumventing the oxidative dehydrogenation of dihydropyrimidine intermediates. This preparative process has also been adapted to a one-pot protocol.</description><subject>Benzamidines</subject><subject>Chloral</subject><subject>Chloroform</subject><subject>Dehydration</subject><subject>Dehydrogenation</subject><subject>Pyrimidines</subject><subject>Synthesis (chemistry)</subject><subject>Tetrahedrons</subject><subject>Trichloroethylideneacetophenones</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp9UE1LxDAQDaLguvoPPOTowdakSb8uwrL4BQte9BzSZGqztE1Nsiv992apZ2cGhmHee_AeQreUpJTQ4mGfBgg9hDQjlKWkjJOfoRWtSpawvKLnaEUIJwknrL5EV97vSayiIit02OARfrAZJmePoPEAobMat9bh0AH28xiXNx7bFmf3PNFGurmfZmcGo80IHvsgXTDjF26dHSImdhKcUV1vnY1qc280jCAVBDt1MNpIukYXrew93PztNfp8fvrYvia795e37WaXKMbqkJRQEN7UushKDozmBSW1bHXVtBUrci6zuiZcVyWRGahG5lmTyyKPVxu_JaVsje4W3eju-wA-iMF4BX0vR7AHL2jJeYwhq05QvkCVs947aMUUPUazghJxSlnsxZKyOKUsSBknj7THhQbRxtGAE14ZGBVo40AFoa35X-AX7XaJBQ</recordid><startdate>20130911</startdate><enddate>20130911</enddate><creator>Guirado, Antonio</creator><creator>Alarcón, Enrique</creator><creator>Vicente, Yesica</creator><creator>Andreu, Raquel</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20130911</creationdate><title>A new improved method for the synthesis of 2,4-diarylpyrimidines starting from 2,2,2-trichloroethylideneacetophenones</title><author>Guirado, Antonio ; Alarcón, Enrique ; Vicente, Yesica ; Andreu, Raquel</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c339t-7e604b9d6274e3156109afd8bf83654a29904d870a2ecba52b5a650a2f6547113</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Benzamidines</topic><topic>Chloral</topic><topic>Chloroform</topic><topic>Dehydration</topic><topic>Dehydrogenation</topic><topic>Pyrimidines</topic><topic>Synthesis (chemistry)</topic><topic>Tetrahedrons</topic><topic>Trichloroethylideneacetophenones</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Guirado, Antonio</creatorcontrib><creatorcontrib>Alarcón, Enrique</creatorcontrib><creatorcontrib>Vicente, Yesica</creatorcontrib><creatorcontrib>Andreu, Raquel</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Guirado, Antonio</au><au>Alarcón, Enrique</au><au>Vicente, Yesica</au><au>Andreu, Raquel</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A new improved method for the synthesis of 2,4-diarylpyrimidines starting from 2,2,2-trichloroethylideneacetophenones</atitle><jtitle>Tetrahedron letters</jtitle><date>2013-09-11</date><risdate>2013</risdate><volume>54</volume><issue>37</issue><spage>5115</spage><epage>5117</epage><pages>5115-5117</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>An advantageous new approach to 2,4-diarylpyrimidines has been developed. 2,2,2-Trichloroethylideneacetophenones reacted with benzamidines leading to novel 2,6-diaryl-6-hydroxy-4-trichloromethyl-1,4,5,6-tetrahydropyrimidines in near quantitative yields. These compounds were efficiently dehydrated to obtain previously unknown 2,4-diaryl-6-trichloromethyl-1,6-dihydropyrimidines, which were able to undergo aromatisation via chloroform elimination to give 2,4-diarylpyrimidines in high yields. A main improvement of this procedure lies in circumventing the oxidative dehydrogenation of dihydropyrimidine intermediates. This preparative process has also been adapted to a one-pot protocol.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2013.07.075</doi><tpages>3</tpages></addata></record> |
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| ispartof | Tetrahedron letters, 2013-09, Vol.54 (37), p.5115-5117 |
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| language | eng |
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| source | Elsevier ScienceDirect Journals Complete |
| subjects | Benzamidines Chloral Chloroform Dehydration Dehydrogenation Pyrimidines Synthesis (chemistry) Tetrahedrons Trichloroethylideneacetophenones |
| title | A new improved method for the synthesis of 2,4-diarylpyrimidines starting from 2,2,2-trichloroethylideneacetophenones |
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