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Three-Component Synthesis of 7-Hydroxy-7-polyfluoroalkylhexahydroimidazo[1,2-a]pyridin-5(1H)-ones
A new straightforward three‐component approach to 7‐hydroxy‐7‐(polyfluoroalkyl)hexahydroimidazo[1,2‐a]pyridin‐5(1H)‐ones with high diastereoselectivity and regiospecificity was developed starting from commercially available 3‐oxo esters, methyl ketones, and 1,2‐ethanediamines. The scope of this cycl...
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| Published in: | European journal of organic chemistry 2015-10, Vol.2015 (28), p.6306-6314 |
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| Main Authors: | , , , , , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c4252-5c4ceb6448c9b0768e48eae554c3c787a00316053ffbb5d6da26a12c8c6268053 |
| container_end_page | 6314 |
| container_issue | 28 |
| container_start_page | 6306 |
| container_title | European journal of organic chemistry |
| container_volume | 2015 |
| creator | Goryaeva, Marina V. Burgart, Yanina V. Kudyakova, Yulia S. Ezhikova, Marina A. Kodess, Mikhail I. Slepukhin, Pavel A. Saloutin, Victor I. |
| description | A new straightforward three‐component approach to 7‐hydroxy‐7‐(polyfluoroalkyl)hexahydroimidazo[1,2‐a]pyridin‐5(1H)‐ones with high diastereoselectivity and regiospecificity was developed starting from commercially available 3‐oxo esters, methyl ketones, and 1,2‐ethanediamines. The scope of this cyclization and its plausible mechanism are reported.
The construction of polyfluoroalkylated hexahydroimidazo[1,2‐a]pyridin‐5(1H)‐ones was carried out in a one‐pot reaction starting from methyl ketones, 1,2‐ethanediamines, and fluorinated 3‐oxo esters. |
| doi_str_mv | 10.1002/ejoc.201500822 |
| format | article |
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The construction of polyfluoroalkylated hexahydroimidazo[1,2‐a]pyridin‐5(1H)‐ones was carried out in a one‐pot reaction starting from methyl ketones, 1,2‐ethanediamines, and fluorinated 3‐oxo esters.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201500822</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Amines ; Cyclization ; Fluorine ; Ketones ; Multicomponent reactions ; Nitrogen heterocycles</subject><ispartof>European journal of organic chemistry, 2015-10, Vol.2015 (28), p.6306-6314</ispartof><rights>Copyright © 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4252-5c4ceb6448c9b0768e48eae554c3c787a00316053ffbb5d6da26a12c8c6268053</citedby><cites>FETCH-LOGICAL-c4252-5c4ceb6448c9b0768e48eae554c3c787a00316053ffbb5d6da26a12c8c6268053</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Goryaeva, Marina V.</creatorcontrib><creatorcontrib>Burgart, Yanina V.</creatorcontrib><creatorcontrib>Kudyakova, Yulia S.</creatorcontrib><creatorcontrib>Ezhikova, Marina A.</creatorcontrib><creatorcontrib>Kodess, Mikhail I.</creatorcontrib><creatorcontrib>Slepukhin, Pavel A.</creatorcontrib><creatorcontrib>Saloutin, Victor I.</creatorcontrib><title>Three-Component Synthesis of 7-Hydroxy-7-polyfluoroalkylhexahydroimidazo[1,2-a]pyridin-5(1H)-ones</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>A new straightforward three‐component approach to 7‐hydroxy‐7‐(polyfluoroalkyl)hexahydroimidazo[1,2‐a]pyridin‐5(1H)‐ones with high diastereoselectivity and regiospecificity was developed starting from commercially available 3‐oxo esters, methyl ketones, and 1,2‐ethanediamines. The scope of this cyclization and its plausible mechanism are reported.
The construction of polyfluoroalkylated hexahydroimidazo[1,2‐a]pyridin‐5(1H)‐ones was carried out in a one‐pot reaction starting from methyl ketones, 1,2‐ethanediamines, and fluorinated 3‐oxo esters.</description><subject>Amines</subject><subject>Cyclization</subject><subject>Fluorine</subject><subject>Ketones</subject><subject>Multicomponent reactions</subject><subject>Nitrogen heterocycles</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkE1Lw0AQhoMoWD-ungteFNw6-5nkKKW2arUHIwoiy3azoWnTbNxtsfE_-Sf8ZaZUijdPM8w8zwy8QXCCoYMByKWZWt0hgDlARMhO0MIQxwhEDLtNzyhDOKYv-8GB91MAiIXArUAnE2cM6tp5ZUtTLtqPdbmYGJ_7ts3aIRrUqbOrGoWoskWdFUvrrCpmdTExKzVZL_N5nqpP-4ovCFJv319V7fI0LxE_w4Nz1Bz1R8Fepgpvjn_rYfB03Uu6AzQc9W-6V0OkGeEEcc20GQvGIh2PIRSRYZFRhnOmqQ6jUAFQLIDTLBuPeSpSRYTCREdaEBE188PgdHO3cvZ9afxCTu3Slc1LiUPcQJRT1lCdDaWd9d6ZTFYunytXSwxyHaRcBym3QTZCvBE-8sLU_9Cydzvq_nXRxs39wqy2rnIzKUIacvn80JfPd-w-SYZ38oX-AEAQh3U</recordid><startdate>201510</startdate><enddate>201510</enddate><creator>Goryaeva, Marina V.</creator><creator>Burgart, Yanina V.</creator><creator>Kudyakova, Yulia S.</creator><creator>Ezhikova, Marina A.</creator><creator>Kodess, Mikhail I.</creator><creator>Slepukhin, Pavel A.</creator><creator>Saloutin, Victor I.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201510</creationdate><title>Three-Component Synthesis of 7-Hydroxy-7-polyfluoroalkylhexahydroimidazo[1,2-a]pyridin-5(1H)-ones</title><author>Goryaeva, Marina V. ; Burgart, Yanina V. ; Kudyakova, Yulia S. ; Ezhikova, Marina A. ; Kodess, Mikhail I. ; Slepukhin, Pavel A. ; Saloutin, Victor I.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4252-5c4ceb6448c9b0768e48eae554c3c787a00316053ffbb5d6da26a12c8c6268053</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Amines</topic><topic>Cyclization</topic><topic>Fluorine</topic><topic>Ketones</topic><topic>Multicomponent reactions</topic><topic>Nitrogen heterocycles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Goryaeva, Marina V.</creatorcontrib><creatorcontrib>Burgart, Yanina V.</creatorcontrib><creatorcontrib>Kudyakova, Yulia S.</creatorcontrib><creatorcontrib>Ezhikova, Marina A.</creatorcontrib><creatorcontrib>Kodess, Mikhail I.</creatorcontrib><creatorcontrib>Slepukhin, Pavel A.</creatorcontrib><creatorcontrib>Saloutin, Victor I.</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Goryaeva, Marina V.</au><au>Burgart, Yanina V.</au><au>Kudyakova, Yulia S.</au><au>Ezhikova, Marina A.</au><au>Kodess, Mikhail I.</au><au>Slepukhin, Pavel A.</au><au>Saloutin, Victor I.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Three-Component Synthesis of 7-Hydroxy-7-polyfluoroalkylhexahydroimidazo[1,2-a]pyridin-5(1H)-ones</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2015-10</date><risdate>2015</risdate><volume>2015</volume><issue>28</issue><spage>6306</spage><epage>6314</epage><pages>6306-6314</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A new straightforward three‐component approach to 7‐hydroxy‐7‐(polyfluoroalkyl)hexahydroimidazo[1,2‐a]pyridin‐5(1H)‐ones with high diastereoselectivity and regiospecificity was developed starting from commercially available 3‐oxo esters, methyl ketones, and 1,2‐ethanediamines. The scope of this cyclization and its plausible mechanism are reported.
The construction of polyfluoroalkylated hexahydroimidazo[1,2‐a]pyridin‐5(1H)‐ones was carried out in a one‐pot reaction starting from methyl ketones, 1,2‐ethanediamines, and fluorinated 3‐oxo esters.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201500822</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1434-193X |
| ispartof | European journal of organic chemistry, 2015-10, Vol.2015 (28), p.6306-6314 |
| issn | 1434-193X 1099-0690 |
| language | eng |
| recordid | cdi_proquest_journals_1716263534 |
| source | Wiley-Blackwell Read & Publish Collection |
| subjects | Amines Cyclization Fluorine Ketones Multicomponent reactions Nitrogen heterocycles |
| title | Three-Component Synthesis of 7-Hydroxy-7-polyfluoroalkylhexahydroimidazo[1,2-a]pyridin-5(1H)-ones |
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