The homologous tert-amino effect: a route to fused 2-benzazepine derivatives
2-Cyano- and 2-carbethoxy-3-[2-(pyrrolidin-1-ylmethyl)phenyl]acrylonitriles were prepared through either amination of appropriate 3-[2-(bromomethyl)phenyl]acrylonitriles with pyrrolidine or condensation of 2-(pyrrolidin-1-ylmethyl)benzaldehyde with malononitrile and ethyl cyanoacetate. These acrylon...
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| Veröffentlicht in: | Tetrahedron 2011-02, Vol.67 (5), p.1030-1035 |
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| creator | Gorulya, Alexander P. Tverdokhlebov, Anton V. Tolmachev, Andrey A. Shishkin, Oleg V. Shishkina, Svetlana V. |
| description | 2-Cyano- and 2-carbethoxy-3-[2-(pyrrolidin-1-ylmethyl)phenyl]acrylonitriles were prepared through either amination of appropriate 3-[2-(bromomethyl)phenyl]acrylonitriles with pyrrolidine or condensation of 2-(pyrrolidin-1-ylmethyl)benzaldehyde with malononitrile and ethyl cyanoacetate. These acrylonitrile derivatives were shown to undergo easy mutual interconversion with 1-(pyrrolidin-1-yl)indane-2-carbonitriles driven by solvent polarity. Upon heating at 140–150 °C both acrylonitrile and indane derivatives were found to give 2,3,5,10,11,11
a-hexahydro-1
H-pyrrolo[1,2-
b][2]benzazepine-11-carbonitriles. All transformations observed were rationalized in the terms of reactions related to the
tert-amino effect. Furthermore, the corresponding piperidin-1-yl and azepan-1-yl analogs of the above acrylonitriles and indanes were obtained similarly. By analogy their heating afforded 1,2,3,4,6,11,12,12
a-octahydropyrido[1,2-
b][2]benzazepine-12-carbonitriles and 7,8,9,10,11,11
a, 12,13-octahydro-5
H-azepino[1,2-
b][2]benzazepine-12-carbonitriles.
[Display omitted] |
| doi_str_mv | 10.1016/j.tet.2010.11.101 |
| format | Article |
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a-hexahydro-1
H-pyrrolo[1,2-
b][2]benzazepine-11-carbonitriles. All transformations observed were rationalized in the terms of reactions related to the
tert-amino effect. Furthermore, the corresponding piperidin-1-yl and azepan-1-yl analogs of the above acrylonitriles and indanes were obtained similarly. By analogy their heating afforded 1,2,3,4,6,11,12,12
a-octahydropyrido[1,2-
b][2]benzazepine-12-carbonitriles and 7,8,9,10,11,11
a, 12,13-octahydro-5
H-azepino[1,2-
b][2]benzazepine-12-carbonitriles.
[Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2010.11.101</identifier><identifier>CODEN: TETRAB</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>Acrylonitriles ; Alicyclic compounds ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Analogies ; Benzazepine ; Chemistry ; Derivatives ; Exact sciences and technology ; Heating ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Indane ; Organic chemistry ; Polarity ; Preparations and properties ; Rearrangement ; Sigmatropic reaction ; Solvent effect ; Solvents ; Tetrahedrons ; Transformations</subject><ispartof>Tetrahedron, 2011-02, Vol.67 (5), p.1030-1035</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c426t-1553146c4a93436affa75132376eeb1c33c24a52f836699f9dc1b156802dfe613</citedby><cites>FETCH-LOGICAL-c426t-1553146c4a93436affa75132376eeb1c33c24a52f836699f9dc1b156802dfe613</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tet.2010.11.101$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23750793$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Gorulya, Alexander P.</creatorcontrib><creatorcontrib>Tverdokhlebov, Anton V.</creatorcontrib><creatorcontrib>Tolmachev, Andrey A.</creatorcontrib><creatorcontrib>Shishkin, Oleg V.</creatorcontrib><creatorcontrib>Shishkina, Svetlana V.</creatorcontrib><title>The homologous tert-amino effect: a route to fused 2-benzazepine derivatives</title><title>Tetrahedron</title><description>2-Cyano- and 2-carbethoxy-3-[2-(pyrrolidin-1-ylmethyl)phenyl]acrylonitriles were prepared through either amination of appropriate 3-[2-(bromomethyl)phenyl]acrylonitriles with pyrrolidine or condensation of 2-(pyrrolidin-1-ylmethyl)benzaldehyde with malononitrile and ethyl cyanoacetate. These acrylonitrile derivatives were shown to undergo easy mutual interconversion with 1-(pyrrolidin-1-yl)indane-2-carbonitriles driven by solvent polarity. Upon heating at 140–150 °C both acrylonitrile and indane derivatives were found to give 2,3,5,10,11,11
a-hexahydro-1
H-pyrrolo[1,2-
b][2]benzazepine-11-carbonitriles. All transformations observed were rationalized in the terms of reactions related to the
tert-amino effect. Furthermore, the corresponding piperidin-1-yl and azepan-1-yl analogs of the above acrylonitriles and indanes were obtained similarly. By analogy their heating afforded 1,2,3,4,6,11,12,12
a-octahydropyrido[1,2-
b][2]benzazepine-12-carbonitriles and 7,8,9,10,11,11
a, 12,13-octahydro-5
H-azepino[1,2-
b][2]benzazepine-12-carbonitriles.
[Display omitted]</description><subject>Acrylonitriles</subject><subject>Alicyclic compounds</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Analogies</subject><subject>Benzazepine</subject><subject>Chemistry</subject><subject>Derivatives</subject><subject>Exact sciences and technology</subject><subject>Heating</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Indane</subject><subject>Organic chemistry</subject><subject>Polarity</subject><subject>Preparations and properties</subject><subject>Rearrangement</subject><subject>Sigmatropic reaction</subject><subject>Solvent effect</subject><subject>Solvents</subject><subject>Tetrahedrons</subject><subject>Transformations</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNp9UE1LAzEUDKJg_fgB3nIRvGzNS7LZrp5E_IKCFz2HNPtiU7abmqQF_fVmqXj09HiPmXkzQ8gFsCkwUNeracY85WzcYTwdkAlIJatagjokE8YkqyTj7JicpLRijAFwMSHztyXSZViHPnyEbaIZY67M2g-BonNo8w01NIZtRpoDdduEHeXVAodv840bPyDtMPqdyX6H6YwcOdMnPP-dp-T98eHt_rmavz693N_NKyu5yhXUtSjerDStkEIZ50xTg-CiUYgLsEJYLk3N3Uwo1bau7SwsoFYzxjuHCsQpudrrbmL43GLKeu2Txb43A5YQGhopVaNY0xQo7KE2hpQiOr2Jfm3ilwamx-b0Spfm9NicBhhPhXP5K2-SNb2LZrA-_RGLz5o1rSi42z0OS9adx6iT9ThY7Hwszeku-H--_ADuzoIo</recordid><startdate>20110204</startdate><enddate>20110204</enddate><creator>Gorulya, Alexander P.</creator><creator>Tverdokhlebov, Anton V.</creator><creator>Tolmachev, Andrey A.</creator><creator>Shishkin, Oleg V.</creator><creator>Shishkina, Svetlana V.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><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>20110204</creationdate><title>The homologous tert-amino effect: a route to fused 2-benzazepine derivatives</title><author>Gorulya, Alexander P. ; Tverdokhlebov, Anton V. ; Tolmachev, Andrey A. ; Shishkin, Oleg V. ; Shishkina, Svetlana V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c426t-1553146c4a93436affa75132376eeb1c33c24a52f836699f9dc1b156802dfe613</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Acrylonitriles</topic><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Analogies</topic><topic>Benzazepine</topic><topic>Chemistry</topic><topic>Derivatives</topic><topic>Exact sciences and technology</topic><topic>Heating</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Indane</topic><topic>Organic chemistry</topic><topic>Polarity</topic><topic>Preparations and properties</topic><topic>Rearrangement</topic><topic>Sigmatropic reaction</topic><topic>Solvent effect</topic><topic>Solvents</topic><topic>Tetrahedrons</topic><topic>Transformations</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gorulya, Alexander P.</creatorcontrib><creatorcontrib>Tverdokhlebov, Anton V.</creatorcontrib><creatorcontrib>Tolmachev, Andrey A.</creatorcontrib><creatorcontrib>Shishkin, Oleg V.</creatorcontrib><creatorcontrib>Shishkina, Svetlana V.</creatorcontrib><collection>Pascal-Francis</collection><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</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gorulya, Alexander P.</au><au>Tverdokhlebov, Anton V.</au><au>Tolmachev, Andrey A.</au><au>Shishkin, Oleg V.</au><au>Shishkina, Svetlana V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The homologous tert-amino effect: a route to fused 2-benzazepine derivatives</atitle><jtitle>Tetrahedron</jtitle><date>2011-02-04</date><risdate>2011</risdate><volume>67</volume><issue>5</issue><spage>1030</spage><epage>1035</epage><pages>1030-1035</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><coden>TETRAB</coden><abstract>2-Cyano- and 2-carbethoxy-3-[2-(pyrrolidin-1-ylmethyl)phenyl]acrylonitriles were prepared through either amination of appropriate 3-[2-(bromomethyl)phenyl]acrylonitriles with pyrrolidine or condensation of 2-(pyrrolidin-1-ylmethyl)benzaldehyde with malononitrile and ethyl cyanoacetate. These acrylonitrile derivatives were shown to undergo easy mutual interconversion with 1-(pyrrolidin-1-yl)indane-2-carbonitriles driven by solvent polarity. Upon heating at 140–150 °C both acrylonitrile and indane derivatives were found to give 2,3,5,10,11,11
a-hexahydro-1
H-pyrrolo[1,2-
b][2]benzazepine-11-carbonitriles. All transformations observed were rationalized in the terms of reactions related to the
tert-amino effect. Furthermore, the corresponding piperidin-1-yl and azepan-1-yl analogs of the above acrylonitriles and indanes were obtained similarly. By analogy their heating afforded 1,2,3,4,6,11,12,12
a-octahydropyrido[1,2-
b][2]benzazepine-12-carbonitriles and 7,8,9,10,11,11
a, 12,13-octahydro-5
H-azepino[1,2-
b][2]benzazepine-12-carbonitriles.
[Display omitted]</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.tet.2010.11.101</doi><tpages>6</tpages></addata></record> |
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| subjects | Acrylonitriles Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Analogies Benzazepine Chemistry Derivatives Exact sciences and technology Heating Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Indane Organic chemistry Polarity Preparations and properties Rearrangement Sigmatropic reaction Solvent effect Solvents Tetrahedrons Transformations |
| title | The homologous tert-amino effect: a route to fused 2-benzazepine derivatives |
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