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Practical Synthesis of α-Perfluoroalkyl Cyclic Imines and Amines
Abstract A convenient and simple approach for the preparation of α-CF 3 and α-C 2 F 5 substituted pyrrolines, tetrahydropyridines, tetrahydroazepine is described. Claisen condensation of N-protected cyclic amides with esters of perfluorocarboxylic acids followed by deprotection and decarboxylation i...
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| Published in: | Synthesis (Stuttgart) 2010-01, Vol.2010 (1), p.120-126 |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c277t-6e94275744758e2095b00f744abcaff43612cda7970a259dc27837f92b9fea0c3 |
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| container_end_page | 126 |
| container_issue | 1 |
| container_start_page | 120 |
| container_title | Synthesis (Stuttgart) |
| container_volume | 2010 |
| creator | Shevchenko, Nikolay E. Balenkova, Elisabeth S. Röschenthaler, Gerd-Volker Nenajdenko, Valentine G. |
| description | Abstract
A convenient and simple approach for the preparation of α-CF
3
and α-C
2
F
5
substituted
pyrrolines, tetrahydropyridines, tetrahydroazepine is described.
Claisen condensation of N-protected cyclic amides with esters of
perfluorocarboxylic acids followed by deprotection and decarboxylation
in acidic media leads to the desired products. Reduction of these
imines permits to obtain 5-, 6-, and 7-membered cyclic amines with α-CF
3
or α-C
2
F
5
group
in good to moderate overall yields. |
| doi_str_mv | 10.1055/s-0029-1217104 |
| format | article |
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A convenient and simple approach for the preparation of α-CF
3
and α-C
2
F
5
substituted
pyrrolines, tetrahydropyridines, tetrahydroazepine is described.
Claisen condensation of N-protected cyclic amides with esters of
perfluorocarboxylic acids followed by deprotection and decarboxylation
in acidic media leads to the desired products. Reduction of these
imines permits to obtain 5-, 6-, and 7-membered cyclic amines with α-CF
3
or α-C
2
F
5
group
in good to moderate overall yields.</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-0029-1217104</identifier><language>eng</language><ispartof>Synthesis (Stuttgart), 2010-01, Vol.2010 (1), p.120-126</ispartof><rights>Georg Thieme Verlag Stuttgart ˙ New York</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c277t-6e94275744758e2095b00f744abcaff43612cda7970a259dc27837f92b9fea0c3</citedby></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-0029-1217104.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0029-1217104$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,780,784,3017,3018,27924,27925,54559,54560</link.rule.ids></links><search><creatorcontrib>Shevchenko, Nikolay E.</creatorcontrib><creatorcontrib>Balenkova, Elisabeth S.</creatorcontrib><creatorcontrib>Röschenthaler, Gerd-Volker</creatorcontrib><creatorcontrib>Nenajdenko, Valentine G.</creatorcontrib><title>Practical Synthesis of α-Perfluoroalkyl Cyclic Imines and Amines</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract
A convenient and simple approach for the preparation of α-CF
3
and α-C
2
F
5
substituted
pyrrolines, tetrahydropyridines, tetrahydroazepine is described.
Claisen condensation of N-protected cyclic amides with esters of
perfluorocarboxylic acids followed by deprotection and decarboxylation
in acidic media leads to the desired products. Reduction of these
imines permits to obtain 5-, 6-, and 7-membered cyclic amines with α-CF
3
or α-C
2
F
5
group
in good to moderate overall yields.</description><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNp1kMtKxDAUhoMoOI5uXecFMp4k7aRZluJlYMABFdyFNE2YjGkrSWfRx_JFfCY7l62rcw6c7-fnQ-iewoJCnj8kAsAkoYwKCtkFmtGMC8IofF6iGQCXRBQFvUY3Ke0AQDAuZ6jcRG0Gb3TAb2M3bG3yCfcO__6QjY0u7PvY6_A1BlyNJniDV63vbMK6a3B5XG_RldMh2bvznKOPp8f36oWsX59XVbkmhgkxkKWVGRO5yDKRF5aBzGsAN526Ntq5jC8pM40WUoBmuWwmquDCSVZLZzUYPkeLU66JfUrROvUdfavjqCiogwCV1EGAOguYAHIChq23rVW7fh-7qeF__3-UeFwk</recordid><startdate>20100101</startdate><enddate>20100101</enddate><creator>Shevchenko, Nikolay E.</creator><creator>Balenkova, Elisabeth S.</creator><creator>Röschenthaler, Gerd-Volker</creator><creator>Nenajdenko, Valentine G.</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20100101</creationdate><title>Practical Synthesis of α-Perfluoroalkyl Cyclic Imines and Amines</title><author>Shevchenko, Nikolay E. ; Balenkova, Elisabeth S. ; Röschenthaler, Gerd-Volker ; Nenajdenko, Valentine G.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c277t-6e94275744758e2095b00f744abcaff43612cda7970a259dc27837f92b9fea0c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shevchenko, Nikolay E.</creatorcontrib><creatorcontrib>Balenkova, Elisabeth S.</creatorcontrib><creatorcontrib>Röschenthaler, Gerd-Volker</creatorcontrib><creatorcontrib>Nenajdenko, Valentine G.</creatorcontrib><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shevchenko, Nikolay E.</au><au>Balenkova, Elisabeth S.</au><au>Röschenthaler, Gerd-Volker</au><au>Nenajdenko, Valentine G.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Practical Synthesis of α-Perfluoroalkyl Cyclic Imines and Amines</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2010-01-01</date><risdate>2010</risdate><volume>2010</volume><issue>1</issue><spage>120</spage><epage>126</epage><pages>120-126</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract
A convenient and simple approach for the preparation of α-CF
3
and α-C
2
F
5
substituted
pyrrolines, tetrahydropyridines, tetrahydroazepine is described.
Claisen condensation of N-protected cyclic amides with esters of
perfluorocarboxylic acids followed by deprotection and decarboxylation
in acidic media leads to the desired products. Reduction of these
imines permits to obtain 5-, 6-, and 7-membered cyclic amines with α-CF
3
or α-C
2
F
5
group
in good to moderate overall yields.</abstract><doi>10.1055/s-0029-1217104</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0039-7881 |
| ispartof | Synthesis (Stuttgart), 2010-01, Vol.2010 (1), p.120-126 |
| issn | 0039-7881 1437-210X |
| language | eng |
| recordid | cdi_crossref_primary_10_1055_s_0029_1217104 |
| source | Thieme Connect Journals |
| title | Practical Synthesis of α-Perfluoroalkyl Cyclic Imines and Amines |
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