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Tandem regio- and stereospecific cyclization of ethyl isonicotinate with cyanoacetylenic alcohols to provide novel polycondensed heterocyclic systems
Ethyl isonicotinate reacts with tertiary cyanoacetylenic alcohols under exceptionally mild conditions (room temperature, without catalyst or solvent) to afford novel polycondensed heterocyclic systems, 4,15-dioxa-7,12-diazapentacyclo[9.5.2.0 2,10.0 3,7.0 12,16]octadeca-8,17-dienes, in 30–68% yields....
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| Published in: | Tetrahedron letters 2012-02, Vol.53 (8), p.927-930 |
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| Main Authors: | , , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c339t-cca24d0e2356a73d643a45f5a26d43253b914247ce03e05a53d82dd9ca4e4e2e3 |
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| cites | cdi_FETCH-LOGICAL-c339t-cca24d0e2356a73d643a45f5a26d43253b914247ce03e05a53d82dd9ca4e4e2e3 |
| container_end_page | 930 |
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| container_start_page | 927 |
| container_title | Tetrahedron letters |
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| creator | Trofimov, Boris A. Mal’kina, Anastasiya G. Nosyreva, Valentina V. Shemyakina, Olesya A. Albanov, Alexander I. Afonin, Andrei V. Kazheva, Olga N. Alexandrov, Grigorii G. Dyachenko, Oleg A. |
| description | Ethyl isonicotinate reacts with tertiary cyanoacetylenic alcohols under exceptionally mild conditions (room temperature, without catalyst or solvent) to afford novel polycondensed heterocyclic systems, 4,15-dioxa-7,12-diazapentacyclo[9.5.2.0
2,10.0
3,7.0
12,16]octadeca-8,17-dienes, in 30–68% yields. This tandem cyclization is regio- and stereospecific. Despite several asymmetric carbons (up to six) being present in the molecules, only one diastereomer is formed and both cyanomethylidene fragments possess exclusively
Z-configuration. The tandem sequence includes the formation of 1,3-oxazolidino-1,2-dihydropyridines which undergo Diels–Alder cyclodimerization to give the final products. |
| doi_str_mv | 10.1016/j.tetlet.2011.12.035 |
| format | article |
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2,10.0
3,7.0
12,16]octadeca-8,17-dienes, in 30–68% yields. This tandem cyclization is regio- and stereospecific. Despite several asymmetric carbons (up to six) being present in the molecules, only one diastereomer is formed and both cyanomethylidene fragments possess exclusively
Z-configuration. The tandem sequence includes the formation of 1,3-oxazolidino-1,2-dihydropyridines which undergo Diels–Alder cyclodimerization to give the final products.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2011.12.035</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>1,2-Dihydropyridines ; 4,15-Dioxa-7,12-diazapentacyclo[9.5.2.0 2,10.0 3,7.0 12,16]octadeca-8,17-dienes ; Alcohols ; Asymmetry ; Carbon ; Catalysts ; Diels–Alder cyclodimerization ; Ethyl isonicotinate ; Formations ; Fragments ; Solvents ; Tandem reaction ; Tertiary cyanoacetylenic alcohols ; Tetrahedrons</subject><ispartof>Tetrahedron letters, 2012-02, Vol.53 (8), p.927-930</ispartof><rights>2011 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c339t-cca24d0e2356a73d643a45f5a26d43253b914247ce03e05a53d82dd9ca4e4e2e3</citedby><cites>FETCH-LOGICAL-c339t-cca24d0e2356a73d643a45f5a26d43253b914247ce03e05a53d82dd9ca4e4e2e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Trofimov, Boris A.</creatorcontrib><creatorcontrib>Mal’kina, Anastasiya G.</creatorcontrib><creatorcontrib>Nosyreva, Valentina V.</creatorcontrib><creatorcontrib>Shemyakina, Olesya A.</creatorcontrib><creatorcontrib>Albanov, Alexander I.</creatorcontrib><creatorcontrib>Afonin, Andrei V.</creatorcontrib><creatorcontrib>Kazheva, Olga N.</creatorcontrib><creatorcontrib>Alexandrov, Grigorii G.</creatorcontrib><creatorcontrib>Dyachenko, Oleg A.</creatorcontrib><title>Tandem regio- and stereospecific cyclization of ethyl isonicotinate with cyanoacetylenic alcohols to provide novel polycondensed heterocyclic systems</title><title>Tetrahedron letters</title><description>Ethyl isonicotinate reacts with tertiary cyanoacetylenic alcohols under exceptionally mild conditions (room temperature, without catalyst or solvent) to afford novel polycondensed heterocyclic systems, 4,15-dioxa-7,12-diazapentacyclo[9.5.2.0
2,10.0
3,7.0
12,16]octadeca-8,17-dienes, in 30–68% yields. This tandem cyclization is regio- and stereospecific. Despite several asymmetric carbons (up to six) being present in the molecules, only one diastereomer is formed and both cyanomethylidene fragments possess exclusively
Z-configuration. The tandem sequence includes the formation of 1,3-oxazolidino-1,2-dihydropyridines which undergo Diels–Alder cyclodimerization to give the final products.</description><subject>1,2-Dihydropyridines</subject><subject>4,15-Dioxa-7,12-diazapentacyclo[9.5.2.0 2,10.0 3,7.0 12,16]octadeca-8,17-dienes</subject><subject>Alcohols</subject><subject>Asymmetry</subject><subject>Carbon</subject><subject>Catalysts</subject><subject>Diels–Alder cyclodimerization</subject><subject>Ethyl isonicotinate</subject><subject>Formations</subject><subject>Fragments</subject><subject>Solvents</subject><subject>Tandem reaction</subject><subject>Tertiary cyanoacetylenic alcohols</subject><subject>Tetrahedrons</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNp9Uc1uFDEMjhCVWErfgEOOXGbI38zsXJBQBQWpUi_lHKWOp5tVNl6SdNHwHrwvKcu5vliWvx9bH2PvpeilkOPHfV-xRqy9ElL2UvVCD6_YRm4n3elhK1-zjRBGdEbo-Q17W8petBq3YsP-3Lvk8cAzPgbqeBt4qZiRyhEhLAE4rBDDb1cDJU4Lx7pbIw-FUgCqIbmK_Feou4ZziRxgXSO2HXcRaEex8Er8mOkUPPJEJ4z8SHEFarapoOc7bH70zwV4WZv7obxjF4uLBa_-90v24-uX--tv3e3dzffrz7cdaD3XDsAp4wUqPYxu0n402plhGZwavdFq0A-zNMpMgEKjGNyg_VZ5P4MzaFChvmQfzrrtwJ9PWKo9hAIYo0tIT8XKyZhxGsWsG9ScoZCplIyLPeZwcHm1UtjnFOzenlOwzylYqWxLodE-nWnY3jgFzLZAwAToQ0ao1lN4WeAvnb2XpA</recordid><startdate>20120222</startdate><enddate>20120222</enddate><creator>Trofimov, Boris A.</creator><creator>Mal’kina, Anastasiya G.</creator><creator>Nosyreva, Valentina V.</creator><creator>Shemyakina, Olesya A.</creator><creator>Albanov, Alexander I.</creator><creator>Afonin, Andrei V.</creator><creator>Kazheva, Olga N.</creator><creator>Alexandrov, Grigorii G.</creator><creator>Dyachenko, Oleg A.</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>20120222</creationdate><title>Tandem regio- and stereospecific cyclization of ethyl isonicotinate with cyanoacetylenic alcohols to provide novel polycondensed heterocyclic systems</title><author>Trofimov, Boris A. ; Mal’kina, Anastasiya G. ; Nosyreva, Valentina V. ; Shemyakina, Olesya A. ; Albanov, Alexander I. ; Afonin, Andrei V. ; Kazheva, Olga N. ; Alexandrov, Grigorii G. ; Dyachenko, Oleg A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c339t-cca24d0e2356a73d643a45f5a26d43253b914247ce03e05a53d82dd9ca4e4e2e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>1,2-Dihydropyridines</topic><topic>4,15-Dioxa-7,12-diazapentacyclo[9.5.2.0 2,10.0 3,7.0 12,16]octadeca-8,17-dienes</topic><topic>Alcohols</topic><topic>Asymmetry</topic><topic>Carbon</topic><topic>Catalysts</topic><topic>Diels–Alder cyclodimerization</topic><topic>Ethyl isonicotinate</topic><topic>Formations</topic><topic>Fragments</topic><topic>Solvents</topic><topic>Tandem reaction</topic><topic>Tertiary cyanoacetylenic alcohols</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Trofimov, Boris A.</creatorcontrib><creatorcontrib>Mal’kina, Anastasiya G.</creatorcontrib><creatorcontrib>Nosyreva, Valentina V.</creatorcontrib><creatorcontrib>Shemyakina, Olesya A.</creatorcontrib><creatorcontrib>Albanov, Alexander I.</creatorcontrib><creatorcontrib>Afonin, Andrei V.</creatorcontrib><creatorcontrib>Kazheva, Olga N.</creatorcontrib><creatorcontrib>Alexandrov, Grigorii G.</creatorcontrib><creatorcontrib>Dyachenko, Oleg A.</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>Trofimov, Boris A.</au><au>Mal’kina, Anastasiya G.</au><au>Nosyreva, Valentina V.</au><au>Shemyakina, Olesya A.</au><au>Albanov, Alexander I.</au><au>Afonin, Andrei V.</au><au>Kazheva, Olga N.</au><au>Alexandrov, Grigorii G.</au><au>Dyachenko, Oleg A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Tandem regio- and stereospecific cyclization of ethyl isonicotinate with cyanoacetylenic alcohols to provide novel polycondensed heterocyclic systems</atitle><jtitle>Tetrahedron letters</jtitle><date>2012-02-22</date><risdate>2012</risdate><volume>53</volume><issue>8</issue><spage>927</spage><epage>930</epage><pages>927-930</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>Ethyl isonicotinate reacts with tertiary cyanoacetylenic alcohols under exceptionally mild conditions (room temperature, without catalyst or solvent) to afford novel polycondensed heterocyclic systems, 4,15-dioxa-7,12-diazapentacyclo[9.5.2.0
2,10.0
3,7.0
12,16]octadeca-8,17-dienes, in 30–68% yields. This tandem cyclization is regio- and stereospecific. Despite several asymmetric carbons (up to six) being present in the molecules, only one diastereomer is formed and both cyanomethylidene fragments possess exclusively
Z-configuration. The tandem sequence includes the formation of 1,3-oxazolidino-1,2-dihydropyridines which undergo Diels–Alder cyclodimerization to give the final products.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2011.12.035</doi><tpages>4</tpages></addata></record> |
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| ispartof | Tetrahedron letters, 2012-02, Vol.53 (8), p.927-930 |
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| language | eng |
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| source | Elsevier |
| subjects | 1,2-Dihydropyridines 4,15-Dioxa-7,12-diazapentacyclo[9.5.2.0 2,10.0 3,7.0 12,16]octadeca-8,17-dienes Alcohols Asymmetry Carbon Catalysts Diels–Alder cyclodimerization Ethyl isonicotinate Formations Fragments Solvents Tandem reaction Tertiary cyanoacetylenic alcohols Tetrahedrons |
| title | Tandem regio- and stereospecific cyclization of ethyl isonicotinate with cyanoacetylenic alcohols to provide novel polycondensed heterocyclic systems |
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