Synthesis of New 2-Vinylation Products of Indole via a Michael-Type Addition Reaction with Dimethyl Acetylenedicarboxylate and Their Diels−Alder Reactivity as Precursors of New Carbazoles
Reaction of 4,7-dihydroindole and dimethyl acetylenedicarboxylate provided a convenient route to functionalized 2-vinylindoles. Diels−Alder reactions of the 2-vinylindoles with naphthoquinone, p-benzoquinone, 1,2-dicyano-4,5-dichloroquinone, N-phenyltriazolinedione, and tetracyanoethylene were inves...
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| Veröffentlicht in: | Journal of organic chemistry 2006-09, Vol.71 (20), p.7793-7799 |
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| container_title | Journal of organic chemistry |
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| creator | CAVDAR, Hiiseyin SARACOGLU, Nurullah |
| description | Reaction of 4,7-dihydroindole and dimethyl acetylenedicarboxylate provided a convenient route to functionalized 2-vinylindoles. Diels−Alder reactions of the 2-vinylindoles with naphthoquinone, p-benzoquinone, 1,2-dicyano-4,5-dichloroquinone, N-phenyltriazolinedione, and tetracyanoethylene were investigated to give [c]annelated 1,2-dihydro, 1,2,3,4-tetrahydro, and fully aromatized carbazoles. The structure and formation mechanism of both 2-vinylindoles and their cycloadduct are discussed. |
| doi_str_mv | 10.1021/jo061336f |
| format | Article |
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Org. Chem</addtitle><description>Reaction of 4,7-dihydroindole and dimethyl acetylenedicarboxylate provided a convenient route to functionalized 2-vinylindoles. Diels−Alder reactions of the 2-vinylindoles with naphthoquinone, p-benzoquinone, 1,2-dicyano-4,5-dichloroquinone, N-phenyltriazolinedione, and tetracyanoethylene were investigated to give [c]annelated 1,2-dihydro, 1,2,3,4-tetrahydro, and fully aromatized carbazoles. The structure and formation mechanism of both 2-vinylindoles and their cycloadduct are discussed.</description><subject>Carbazoles - chemical synthesis</subject><subject>Carbazoles - chemistry</subject><subject>Carboxylic Acids - chemistry</subject><subject>Chemistry</subject><subject>Condensed benzenic and aromatic compounds</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Indoles - chemistry</subject><subject>Molecular Structure</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Vinyl Compounds - chemical synthesis</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc1u1DAURiMEokNhwQsgb6jEIuCfOHGWoyktHRWoaECITeSxrzUunmSwk7bhCbru-_AyPAnuTDSzwZtr6R4dffpukrwk-C3BlLy7anFOGMvNo2RCOMVpXuLscTLBmNKU0ZwdJM9CuMLxcc6fJgckL0ueCzFJ_lwOTbeEYANqDfoEN4im32wzONnZtkEXvtW96jbLs0a3DtC1lUiij1YtJbi0GtaAplrbDf4FpNp8bmy3RMd2Bd1ycGiqoBscNKCtkn7R3j7oAclGo2oJ1kcSXPh7dz91GvxoubbdgGSIEUD1PrR-l3AWHfJ3zBKeJ0-MdAFejPMw-Xryvpp9SM8_n57NpuepZIJ0KRSZJkoUmhsjtcoUzkTJOGQlLRcm9kMNJ0xqUzKKiSgkUCEW2kBRUFUyYIfJ0da79u2vHkJXr2xQ4JxsoO1DHasUBRFZBN9sQeXbEDyYeu3tSvqhJrh-uFW9u1VkX43SfrECvSfH40Tg9QjIoKQzXjbKhj0nCM8ywSOXbjkbOrjd7aX_WecFK3hdXVzW8-P5ybz6flr_2HulCjFP75vY3X8C_gPofLvx</recordid><startdate>20060929</startdate><enddate>20060929</enddate><creator>CAVDAR, Hiiseyin</creator><creator>SARACOGLU, Nurullah</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20060929</creationdate><title>Synthesis of New 2-Vinylation Products of Indole via a Michael-Type Addition Reaction with Dimethyl Acetylenedicarboxylate and Their Diels−Alder Reactivity as Precursors of New Carbazoles</title><author>CAVDAR, Hiiseyin ; SARACOGLU, Nurullah</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-e74d1c87d5ffadc4c048935e4929bf2632f513adf9320187ae288bdfe772c93e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Carbazoles - chemical synthesis</topic><topic>Carbazoles - chemistry</topic><topic>Carboxylic Acids - chemistry</topic><topic>Chemistry</topic><topic>Condensed benzenic and aromatic compounds</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Indoles - chemistry</topic><topic>Molecular Structure</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Vinyl Compounds - chemical synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>CAVDAR, Hiiseyin</creatorcontrib><creatorcontrib>SARACOGLU, Nurullah</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>CAVDAR, Hiiseyin</au><au>SARACOGLU, Nurullah</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of New 2-Vinylation Products of Indole via a Michael-Type Addition Reaction with Dimethyl Acetylenedicarboxylate and Their Diels−Alder Reactivity as Precursors of New Carbazoles</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2006-09-29</date><risdate>2006</risdate><volume>71</volume><issue>20</issue><spage>7793</spage><epage>7799</epage><pages>7793-7799</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Reaction of 4,7-dihydroindole and dimethyl acetylenedicarboxylate provided a convenient route to functionalized 2-vinylindoles. Diels−Alder reactions of the 2-vinylindoles with naphthoquinone, p-benzoquinone, 1,2-dicyano-4,5-dichloroquinone, N-phenyltriazolinedione, and tetracyanoethylene were investigated to give [c]annelated 1,2-dihydro, 1,2,3,4-tetrahydro, and fully aromatized carbazoles. The structure and formation mechanism of both 2-vinylindoles and their cycloadduct are discussed.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16995688</pmid><doi>10.1021/jo061336f</doi><tpages>7</tpages></addata></record> |
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| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2006-09, Vol.71 (20), p.7793-7799 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Carbazoles - chemical synthesis Carbazoles - chemistry Carboxylic Acids - chemistry Chemistry Condensed benzenic and aromatic compounds Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Indoles - chemistry Molecular Structure Noncondensed benzenic compounds Organic chemistry Preparations and properties Vinyl Compounds - chemical synthesis |
| title | Synthesis of New 2-Vinylation Products of Indole via a Michael-Type Addition Reaction with Dimethyl Acetylenedicarboxylate and Their Diels−Alder Reactivity as Precursors of New Carbazoles |
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