Transformation of 2-methyl-1-phenylethynyl-1,2,3,4-tetrahydroisoquinoline by the action of activated alkynes
Transformations of 2-methyl-1-phenylethynyl-1,2,3,4-tetrahydroisoquinoline resulting from the action of activated alkynes in trifluoroethanol and hexafluoroisopropanol were studied. In reactions with dimethyl acetylenedicarboxylate, 6-phenylethynyl-substituted benzazocines were prepared, while methy...
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| Veröffentlicht in: | Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2018-05, Vol.54 (5), p.576-580 |
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| container_title | Chemistry of heterocyclic compounds (New York, N.Y. 1965) |
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| creator | Voskressensky, Leonid G. Samavati, Reza Titov, Alexander А. Alexandrova, Elena V. Chernikova, Natalia Yu Varlamov, Alexey V. |
| description | Transformations of 2-methyl-1-phenylethynyl-1,2,3,4-tetrahydroisoquinoline resulting from the action of activated alkynes in trifluoroethanol and hexafluoroisopropanol were studied. In reactions with dimethyl acetylenedicarboxylate, 6-phenylethynyl-substituted benzazocines were prepared, while methyl 4-benzyl-5-(2-ethenylphenyl)-1-methyl-1
H
-pyrrole-3-carboxylate and benzo[
d
][3]-azacyclodeca[4,6,7]triene with the allene fragment, respectively, were isolated in reactions with methyl propiolate and acetylacetylene in addition to the corresponding benzazocines. As a rule, in hexafluoroisopropanol, the yields of azocines are higher. In reaction with acetylacetylene in dichloromethane, 1-(2-acetylvinyl)-1-phenylethynyltetrahydroisoquinoline is formed in high yield. |
| doi_str_mv | 10.1007/s10593-018-2306-y |
| format | Article |
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H
-pyrrole-3-carboxylate and benzo[
d
][3]-azacyclodeca[4,6,7]triene with the allene fragment, respectively, were isolated in reactions with methyl propiolate and acetylacetylene in addition to the corresponding benzazocines. As a rule, in hexafluoroisopropanol, the yields of azocines are higher. In reaction with acetylacetylene in dichloromethane, 1-(2-acetylvinyl)-1-phenylethynyltetrahydroisoquinoline is formed in high yield.</description><identifier>ISSN: 0009-3122</identifier><identifier>EISSN: 1573-8353</identifier><identifier>DOI: 10.1007/s10593-018-2306-y</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Alkynes ; Allene ; Chemistry ; Chemistry and Materials Science ; Dichloromethane ; Organic Chemistry ; Pharmacy ; Pyridine ; Transformations</subject><ispartof>Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2018-05, Vol.54 (5), p.576-580</ispartof><rights>Springer Science+Business Media, LLC, part of Springer Nature 2018</rights><rights>COPYRIGHT 2018 Springer</rights><rights>Copyright Springer Science & Business Media 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c355t-1ad28b79ea6d2b70d3313cd969c83d47a7b12f3f9ec946c0a6a5ca200e95aa1c3</citedby><cites>FETCH-LOGICAL-c355t-1ad28b79ea6d2b70d3313cd969c83d47a7b12f3f9ec946c0a6a5ca200e95aa1c3</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/s10593-018-2306-y$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s10593-018-2306-y$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids></links><search><creatorcontrib>Voskressensky, Leonid G.</creatorcontrib><creatorcontrib>Samavati, Reza</creatorcontrib><creatorcontrib>Titov, Alexander А.</creatorcontrib><creatorcontrib>Alexandrova, Elena V.</creatorcontrib><creatorcontrib>Chernikova, Natalia Yu</creatorcontrib><creatorcontrib>Varlamov, Alexey V.</creatorcontrib><title>Transformation of 2-methyl-1-phenylethynyl-1,2,3,4-tetrahydroisoquinoline by the action of activated alkynes</title><title>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</title><addtitle>Chem Heterocycl Comp</addtitle><description>Transformations of 2-methyl-1-phenylethynyl-1,2,3,4-tetrahydroisoquinoline resulting from the action of activated alkynes in trifluoroethanol and hexafluoroisopropanol were studied. In reactions with dimethyl acetylenedicarboxylate, 6-phenylethynyl-substituted benzazocines were prepared, while methyl 4-benzyl-5-(2-ethenylphenyl)-1-methyl-1
H
-pyrrole-3-carboxylate and benzo[
d
][3]-azacyclodeca[4,6,7]triene with the allene fragment, respectively, were isolated in reactions with methyl propiolate and acetylacetylene in addition to the corresponding benzazocines. As a rule, in hexafluoroisopropanol, the yields of azocines are higher. In reaction with acetylacetylene in dichloromethane, 1-(2-acetylvinyl)-1-phenylethynyltetrahydroisoquinoline is formed in high yield.</description><subject>Alkynes</subject><subject>Allene</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Dichloromethane</subject><subject>Organic Chemistry</subject><subject>Pharmacy</subject><subject>Pyridine</subject><subject>Transformations</subject><issn>0009-3122</issn><issn>1573-8353</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp1kUFP3DAQhS1EJRboD-AWqdc1jO3Ejo8IFVoJiQucrVlnwgay9tYOlfLv6yitOFU-jN_ofeOxHmNXAq4FgLnJAhqrOIiWSwWazydsIxqjeKsadco2AGC5ElKesfOc34o0oq03bHxOGHIf0wGnIYYq9pXkB5r288gFP-4pzOOiwqK3cqu2NZ9oSrifuxSHHH99DCGOQ6BqN1fTnir0_wYtt984UVfh-D4HypfsS49jpq9_6wV7uf_-fPeDPz49_Ly7feReNc3EBXay3RlLqDu5M9ApJZTvrLa-VV1t0OyE7FVvydtae0CNjUcJQLZBFF5dsG_r3GMq-1Ge3Fv8SKE86SRoI6w1EorrenW94khuCH0s3_LldHQYfAzUD6V_29QatG7bBRAr4FPMOVHvjmk4YJqdALek4NYUXEnBLSm4uTByZXLxhldKn6v8H_oDGl-LeQ</recordid><startdate>20180501</startdate><enddate>20180501</enddate><creator>Voskressensky, Leonid G.</creator><creator>Samavati, Reza</creator><creator>Titov, Alexander А.</creator><creator>Alexandrova, Elena V.</creator><creator>Chernikova, Natalia Yu</creator><creator>Varlamov, Alexey V.</creator><general>Springer US</general><general>Springer</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20180501</creationdate><title>Transformation of 2-methyl-1-phenylethynyl-1,2,3,4-tetrahydroisoquinoline by the action of activated alkynes</title><author>Voskressensky, Leonid G. ; Samavati, Reza ; Titov, Alexander А. ; Alexandrova, Elena V. ; Chernikova, Natalia Yu ; Varlamov, Alexey V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c355t-1ad28b79ea6d2b70d3313cd969c83d47a7b12f3f9ec946c0a6a5ca200e95aa1c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alkynes</topic><topic>Allene</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Dichloromethane</topic><topic>Organic Chemistry</topic><topic>Pharmacy</topic><topic>Pyridine</topic><topic>Transformations</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Voskressensky, Leonid G.</creatorcontrib><creatorcontrib>Samavati, Reza</creatorcontrib><creatorcontrib>Titov, Alexander А.</creatorcontrib><creatorcontrib>Alexandrova, Elena V.</creatorcontrib><creatorcontrib>Chernikova, Natalia Yu</creatorcontrib><creatorcontrib>Varlamov, Alexey V.</creatorcontrib><collection>CrossRef</collection><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Voskressensky, Leonid G.</au><au>Samavati, Reza</au><au>Titov, Alexander А.</au><au>Alexandrova, Elena V.</au><au>Chernikova, Natalia Yu</au><au>Varlamov, Alexey V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Transformation of 2-methyl-1-phenylethynyl-1,2,3,4-tetrahydroisoquinoline by the action of activated alkynes</atitle><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle><stitle>Chem Heterocycl Comp</stitle><date>2018-05-01</date><risdate>2018</risdate><volume>54</volume><issue>5</issue><spage>576</spage><epage>580</epage><pages>576-580</pages><issn>0009-3122</issn><eissn>1573-8353</eissn><abstract>Transformations of 2-methyl-1-phenylethynyl-1,2,3,4-tetrahydroisoquinoline resulting from the action of activated alkynes in trifluoroethanol and hexafluoroisopropanol were studied. In reactions with dimethyl acetylenedicarboxylate, 6-phenylethynyl-substituted benzazocines were prepared, while methyl 4-benzyl-5-(2-ethenylphenyl)-1-methyl-1
H
-pyrrole-3-carboxylate and benzo[
d
][3]-azacyclodeca[4,6,7]triene with the allene fragment, respectively, were isolated in reactions with methyl propiolate and acetylacetylene in addition to the corresponding benzazocines. As a rule, in hexafluoroisopropanol, the yields of azocines are higher. In reaction with acetylacetylene in dichloromethane, 1-(2-acetylvinyl)-1-phenylethynyltetrahydroisoquinoline is formed in high yield.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s10593-018-2306-y</doi><tpages>5</tpages></addata></record> |
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| subjects | Alkynes Allene Chemistry Chemistry and Materials Science Dichloromethane Organic Chemistry Pharmacy Pyridine Transformations |
| title | Transformation of 2-methyl-1-phenylethynyl-1,2,3,4-tetrahydroisoquinoline by the action of activated alkynes |
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