Alcohol Mediated Synthesis of 4‑Oxo-2-aryl‑4H‑chromene-3-carboxylate Derivatives from 4‑Hydroxycoumarins
The unusual alcohol mediated formation of 4-oxo-2-aryl-4H-chromene-3-carboxylate (flavone-3-carboxylate) derivatives from 4-hydroxycoumarins and β-nitroalkenes in an alcoholic medium is described. The transformation occurs via the in situ formation of a Michael adduct, followed by the alkoxide ion m...
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| Veröffentlicht in: | Journal of organic chemistry 2012-08, Vol.77 (15), p.6495-6504 |
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| container_end_page | 6504 |
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| container_issue | 15 |
| container_start_page | 6495 |
| container_title | Journal of organic chemistry |
| container_volume | 77 |
| creator | Zanwar, Manoj R Raihan, Mustafa J Gawande, Sachin D Kavala, Veerababurao Janreddy, Donala Kuo, Chun-Wei Ambre, Ram Yao, Ching-Fa |
| description | The unusual alcohol mediated formation of 4-oxo-2-aryl-4H-chromene-3-carboxylate (flavone-3-carboxylate) derivatives from 4-hydroxycoumarins and β-nitroalkenes in an alcoholic medium is described. The transformation occurs via the in situ formation of a Michael adduct, followed by the alkoxide ion mediated rearrangement of the intermediate. The effect of the different alcohol and nonalcohol media on the reaction was investigated. |
| doi_str_mv | 10.1021/jo301044y |
| format | Article |
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The transformation occurs via the in situ formation of a Michael adduct, followed by the alkoxide ion mediated rearrangement of the intermediate. 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Org. Chem</addtitle><description>The unusual alcohol mediated formation of 4-oxo-2-aryl-4H-chromene-3-carboxylate (flavone-3-carboxylate) derivatives from 4-hydroxycoumarins and β-nitroalkenes in an alcoholic medium is described. The transformation occurs via the in situ formation of a Michael adduct, followed by the alkoxide ion mediated rearrangement of the intermediate. The effect of the different alcohol and nonalcohol media on the reaction was investigated.</description><subject>4-Hydroxycoumarins - chemistry</subject><subject>Alcohols - chemistry</subject><subject>Benzopyrans - chemical synthesis</subject><subject>Benzopyrans - chemistry</subject><subject>Chemistry</subject><subject>Crystallography, X-Ray</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkUtOxDAMhiMEguGx4AKoGyQ2Acdp03aJeA0SiAWwrtw01XTUaYakHdEdV-CKnIQAA3hhy9L3-8nYoYBTASjO5laCgDgeN9hEJAhc5RBvsgkAIpeo5A7b9X4OwZIk2WY7iBnkAGLCluettjPbRvemaqg3VfQ4dv3M-MZHto7ij7f3h1fLkZMb25DE0-D0zNmF6QyXXJMr7evYBml0aVyzor5ZGR_VgfhWT8fKBUDbYUGu6fw-26qp9eZgHffY8_XV08WU3z3c3F6c33GSMu15TrVOahRliRXVsgJNIIlKrUmIVJlc5TmVmKVxmRrIskyVNWmdmQqlSjCVe-zkp-7S2ZfB-L5YNF6btqXO2MEXAqQQSmCGAT1ao0O5MFWxdE2YdSx-rxSA4zVAXlNbO-p04_85hRgnoP450r6Y28F1YcPQqfj6UvH3JfkJsLOGPw</recordid><startdate>20120803</startdate><enddate>20120803</enddate><creator>Zanwar, Manoj R</creator><creator>Raihan, Mustafa J</creator><creator>Gawande, Sachin D</creator><creator>Kavala, Veerababurao</creator><creator>Janreddy, Donala</creator><creator>Kuo, Chun-Wei</creator><creator>Ambre, Ram</creator><creator>Yao, Ching-Fa</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20120803</creationdate><title>Alcohol Mediated Synthesis of 4‑Oxo-2-aryl‑4H‑chromene-3-carboxylate Derivatives from 4‑Hydroxycoumarins</title><author>Zanwar, Manoj R ; Raihan, Mustafa J ; Gawande, Sachin D ; Kavala, Veerababurao ; Janreddy, Donala ; Kuo, Chun-Wei ; Ambre, Ram ; Yao, Ching-Fa</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a337t-9afc5f21bb2daf3d0ca03aabcca1176e9699ab2874b7e08886bfacc8ed2365273</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>4-Hydroxycoumarins - chemistry</topic><topic>Alcohols - chemistry</topic><topic>Benzopyrans - chemical synthesis</topic><topic>Benzopyrans - chemistry</topic><topic>Chemistry</topic><topic>Crystallography, X-Ray</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zanwar, Manoj R</creatorcontrib><creatorcontrib>Raihan, Mustafa J</creatorcontrib><creatorcontrib>Gawande, Sachin D</creatorcontrib><creatorcontrib>Kavala, Veerababurao</creatorcontrib><creatorcontrib>Janreddy, Donala</creatorcontrib><creatorcontrib>Kuo, Chun-Wei</creatorcontrib><creatorcontrib>Ambre, Ram</creatorcontrib><creatorcontrib>Yao, Ching-Fa</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zanwar, Manoj R</au><au>Raihan, Mustafa J</au><au>Gawande, Sachin D</au><au>Kavala, Veerababurao</au><au>Janreddy, Donala</au><au>Kuo, Chun-Wei</au><au>Ambre, Ram</au><au>Yao, Ching-Fa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Alcohol Mediated Synthesis of 4‑Oxo-2-aryl‑4H‑chromene-3-carboxylate Derivatives from 4‑Hydroxycoumarins</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2012-08-03</date><risdate>2012</risdate><volume>77</volume><issue>15</issue><spage>6495</spage><epage>6504</epage><pages>6495-6504</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The unusual alcohol mediated formation of 4-oxo-2-aryl-4H-chromene-3-carboxylate (flavone-3-carboxylate) derivatives from 4-hydroxycoumarins and β-nitroalkenes in an alcoholic medium is described. The transformation occurs via the in situ formation of a Michael adduct, followed by the alkoxide ion mediated rearrangement of the intermediate. The effect of the different alcohol and nonalcohol media on the reaction was investigated.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>22809001</pmid><doi>10.1021/jo301044y</doi><tpages>10</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2012-08, Vol.77 (15), p.6495-6504 |
| issn | 0022-3263 1520-6904 |
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| source | MEDLINE; ACS Publications |
| subjects | 4-Hydroxycoumarins - chemistry Alcohols - chemistry Benzopyrans - chemical synthesis Benzopyrans - chemistry Chemistry Crystallography, X-Ray Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Models, Molecular Molecular Structure Organic chemistry Preparations and properties |
| title | Alcohol Mediated Synthesis of 4‑Oxo-2-aryl‑4H‑chromene-3-carboxylate Derivatives from 4‑Hydroxycoumarins |
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