2-(3,4-Dihydro-4-oxo-2-quinazolinyl)acetonitriles in the Synthesis of New Condensed Pyrimidines
Abstract The reaction of the title compounds with 5-chloro-2-(methylsulfonyl/methylthio)pyrimidine-4-carbonyl chlorides afforded a series of new nitriles (6, 7). In the reaction of 6 with aliphatic amines the replacement of the methylsulfonyl group took place to give products 8. Compounds 6 cyclized...
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| Veröffentlicht in: | Synthesis (Stuttgart) 2004-11, Vol.2004 (16), p.2659-2664 |
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| container_title | Synthesis (Stuttgart) |
| container_volume | 2004 |
| creator | Volovenko, Yulian M. Blyumin, Evgeniy V. Volovnenko, Tatiana A. Shokol, Tatiana V. Shishkin, Oleg V. |
| description | Abstract
The reaction of the title compounds with 5-chloro-2-(methylsulfonyl/methylthio)pyrimidine-4-carbonyl chlorides afforded a series of new nitriles (6, 7). In the reaction of 6 with aliphatic amines the replacement of the methylsulfonyl group took place to give products 8. Compounds 6 cyclized into 3-(methylsulfonyl)-5,12-dioxo-7,12-dihydro-5H-pyrimido[4′,5′:5,6]pyrido[2,1-B]quinazoline-6-carbonitriles in the presence of Et
3
N. An X-ray crystallographic study was carried out to confirm the structure of the new compounds unambiguously. The influence of basicity and steric factors on the course of this cyclization was discussed. |
| doi_str_mv | 10.1055/s-2004-834860 |
| format | Article |
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The reaction of the title compounds with 5-chloro-2-(methylsulfonyl/methylthio)pyrimidine-4-carbonyl chlorides afforded a series of new nitriles (6, 7). In the reaction of 6 with aliphatic amines the replacement of the methylsulfonyl group took place to give products 8. Compounds 6 cyclized into 3-(methylsulfonyl)-5,12-dioxo-7,12-dihydro-5H-pyrimido[4′,5′:5,6]pyrido[2,1-B]quinazoline-6-carbonitriles in the presence of Et
3
N. An X-ray crystallographic study was carried out to confirm the structure of the new compounds unambiguously. The influence of basicity and steric factors on the course of this cyclization was discussed.</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-2004-834860</identifier><language>eng</language><ispartof>Synthesis (Stuttgart), 2004-11, Vol.2004 (16), p.2659-2664</ispartof><rights>Georg Thieme Verlag Stuttgart · New York</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2004-834860.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-2004-834860$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,776,780,3005,27901,27902,54534,54535</link.rule.ids></links><search><creatorcontrib>Volovenko, Yulian M.</creatorcontrib><creatorcontrib>Blyumin, Evgeniy V.</creatorcontrib><creatorcontrib>Volovnenko, Tatiana A.</creatorcontrib><creatorcontrib>Shokol, Tatiana V.</creatorcontrib><creatorcontrib>Shishkin, Oleg V.</creatorcontrib><title>2-(3,4-Dihydro-4-oxo-2-quinazolinyl)acetonitriles in the Synthesis of New Condensed Pyrimidines</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract
The reaction of the title compounds with 5-chloro-2-(methylsulfonyl/methylthio)pyrimidine-4-carbonyl chlorides afforded a series of new nitriles (6, 7). In the reaction of 6 with aliphatic amines the replacement of the methylsulfonyl group took place to give products 8. Compounds 6 cyclized into 3-(methylsulfonyl)-5,12-dioxo-7,12-dihydro-5H-pyrimido[4′,5′:5,6]pyrido[2,1-B]quinazoline-6-carbonitriles in the presence of Et
3
N. An X-ray crystallographic study was carried out to confirm the structure of the new compounds unambiguously. The influence of basicity and steric factors on the course of this cyclization was discussed.</description><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNotkM1LwzAchoMoOKdH7zkqLPrLV5seZX7CUEEFbyFtEprRJdh0aP3r7Zin5_a-Dw9C5xSuKEh5nQkDEERxoQo4QDMqeEkYhc9DNAPgFSmVosfoJOc1AJSMVzOkGbngC0FuQzvaPhFB0k8ijHxtQzS_qQtx7C5N44YUw9CHzmUcIh5ah9_GOCGHjJPHz-4bL1O0LmZn8evYh02wIbp8io686bI7--ccfdzfvS8fyerl4Wl5syJ5UgdijFWTrmdNXRuhqBLGV2CKRkolWV3bwgvFyqYpwNaWOlZKXzHpRMN8IWnN52ix3x3a4DZOr9O2j9OhpqB3cXTWuzh6H4f_Acz1V2w</recordid><startdate>20041103</startdate><enddate>20041103</enddate><creator>Volovenko, Yulian M.</creator><creator>Blyumin, Evgeniy V.</creator><creator>Volovnenko, Tatiana A.</creator><creator>Shokol, Tatiana V.</creator><creator>Shishkin, Oleg V.</creator><scope/></search><sort><creationdate>20041103</creationdate><title>2-(3,4-Dihydro-4-oxo-2-quinazolinyl)acetonitriles in the Synthesis of New Condensed Pyrimidines</title><author>Volovenko, Yulian M. ; Blyumin, Evgeniy V. ; Volovnenko, Tatiana A. ; Shokol, Tatiana V. ; Shishkin, Oleg V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-s1050-aad8143f2cbba48184af90a6c55852bbd6f4827cc60dbd1e275f925e4c2f651b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Volovenko, Yulian M.</creatorcontrib><creatorcontrib>Blyumin, Evgeniy V.</creatorcontrib><creatorcontrib>Volovnenko, Tatiana A.</creatorcontrib><creatorcontrib>Shokol, Tatiana V.</creatorcontrib><creatorcontrib>Shishkin, Oleg V.</creatorcontrib><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Volovenko, Yulian M.</au><au>Blyumin, Evgeniy V.</au><au>Volovnenko, Tatiana A.</au><au>Shokol, Tatiana V.</au><au>Shishkin, Oleg V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>2-(3,4-Dihydro-4-oxo-2-quinazolinyl)acetonitriles in the Synthesis of New Condensed Pyrimidines</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2004-11-03</date><risdate>2004</risdate><volume>2004</volume><issue>16</issue><spage>2659</spage><epage>2664</epage><pages>2659-2664</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract
The reaction of the title compounds with 5-chloro-2-(methylsulfonyl/methylthio)pyrimidine-4-carbonyl chlorides afforded a series of new nitriles (6, 7). In the reaction of 6 with aliphatic amines the replacement of the methylsulfonyl group took place to give products 8. Compounds 6 cyclized into 3-(methylsulfonyl)-5,12-dioxo-7,12-dihydro-5H-pyrimido[4′,5′:5,6]pyrido[2,1-B]quinazoline-6-carbonitriles in the presence of Et
3
N. An X-ray crystallographic study was carried out to confirm the structure of the new compounds unambiguously. The influence of basicity and steric factors on the course of this cyclization was discussed.</abstract><doi>10.1055/s-2004-834860</doi><tpages>6</tpages></addata></record> |
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| title | 2-(3,4-Dihydro-4-oxo-2-quinazolinyl)acetonitriles in the Synthesis of New Condensed Pyrimidines |
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