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Syntheses of C12,N13 Heterocyclic Bridged Fused Indenopyrrolocarbazoles
Tandem alkylation/cyclization of indenopyrrolocarbazole 4a, a C12 carbon analogue of indolocarbazole K252c, was carried out by general solid-phase and solution-phase methods. Alkylation of fused pyrroloindenylcarbazole 4a derivatives with appropriate monoacetals of diketones afforded the correspondi...
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Published in: | Journal of organic chemistry 2002-05, Vol.67 (10), p.3235-3241 |
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container_title | Journal of organic chemistry |
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creator | Underiner, Ted L Mallamo, John P Singh, Jasbir |
description | Tandem alkylation/cyclization of indenopyrrolocarbazole 4a, a C12 carbon analogue of indolocarbazole K252c, was carried out by general solid-phase and solution-phase methods. Alkylation of fused pyrroloindenylcarbazole 4a derivatives with appropriate monoacetals of diketones afforded the corresponding C12-substituted acetal alcohols. Acid-catalyzed cyclization of these adducts yielded C12,N13-bridged tetrahydrofuran, pyran, and dioxane compounds 10 − 13. |
doi_str_mv | 10.1021/jo0108360 |
format | article |
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Alkylation of fused pyrroloindenylcarbazole 4a derivatives with appropriate monoacetals of diketones afforded the corresponding C12-substituted acetal alcohols. Acid-catalyzed cyclization of these adducts yielded C12,N13-bridged tetrahydrofuran, pyran, and dioxane compounds 10 − 13.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo0108360</identifier><identifier>PMID: 12003530</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2002-05, Vol.67 (10), p.3235-3241</ispartof><rights>Copyright © 2002 American Chemical Society</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-ab0c41e1bf8c81bc6d03687a5c8181f4d8440719839709304dedd1c9710709cb3</citedby><cites>FETCH-LOGICAL-a379t-ab0c41e1bf8c81bc6d03687a5c8181f4d8440719839709304dedd1c9710709cb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=13665616$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12003530$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Underiner, Ted L</creatorcontrib><creatorcontrib>Mallamo, John P</creatorcontrib><creatorcontrib>Singh, Jasbir</creatorcontrib><title>Syntheses of C12,N13 Heterocyclic Bridged Fused Indenopyrrolocarbazoles</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Tandem alkylation/cyclization of indenopyrrolocarbazole 4a, a C12 carbon analogue of indolocarbazole K252c, was carried out by general solid-phase and solution-phase methods. Alkylation of fused pyrroloindenylcarbazole 4a derivatives with appropriate monoacetals of diketones afforded the corresponding C12-substituted acetal alcohols. Acid-catalyzed cyclization of these adducts yielded C12,N13-bridged tetrahydrofuran, pyran, and dioxane compounds 10 − 13.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</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>2002</creationdate><recordtype>article</recordtype><recordid>eNptkNFP2zAQxi00BKXbw_4BlJdNQiLsLo7t5HErUCo6mFQQe7Mc22FhadzZiUT56zFqRV92D3c63U-fvvsI-YxwhpDhtycHCAXlsEdGyDJIeQn5BzICyLKUZpwekqMQniAWY-yAHGIGQBmFEZku1l3_xwYbElcnE8xOb5AmV7a33um1bhud_PCNebQmuRxC7LPO2M6t1t671mnlK_XiWhs-kv1atcF-2s4xub-8uJtcpfPb6WzyfZ4qKso-VRXoHC1WdaELrDQ3QHkhFItbgXVuijwHgWVBSwElhdxYY1CXAiHuuqJj8nWju_Lu32BDL5dN0LZtVWfdEKRALlj8LIInG1B7F4K3tVz5Zqn8WiLIt9Tke2qRPd6KDtXSmh25jSkCX7aAClq1tVedbsKOo5wzjjxy6YZrQm-f3-_K_5VcUMHk3a-F_Fle_36Yzs_lYqerdIh-Bt_F7P5j8BVLrI0h</recordid><startdate>20020517</startdate><enddate>20020517</enddate><creator>Underiner, Ted L</creator><creator>Mallamo, John P</creator><creator>Singh, Jasbir</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20020517</creationdate><title>Syntheses of C12,N13 Heterocyclic Bridged Fused Indenopyrrolocarbazoles</title><author>Underiner, Ted L ; Mallamo, John P ; Singh, Jasbir</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-ab0c41e1bf8c81bc6d03687a5c8181f4d8440719839709304dedd1c9710709cb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Underiner, Ted L</creatorcontrib><creatorcontrib>Mallamo, John P</creatorcontrib><creatorcontrib>Singh, Jasbir</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</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>Underiner, Ted L</au><au>Mallamo, John P</au><au>Singh, Jasbir</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Syntheses of C12,N13 Heterocyclic Bridged Fused Indenopyrrolocarbazoles</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2002-05-17</date><risdate>2002</risdate><volume>67</volume><issue>10</issue><spage>3235</spage><epage>3241</epage><pages>3235-3241</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Tandem alkylation/cyclization of indenopyrrolocarbazole 4a, a C12 carbon analogue of indolocarbazole K252c, was carried out by general solid-phase and solution-phase methods. Alkylation of fused pyrroloindenylcarbazole 4a derivatives with appropriate monoacetals of diketones afforded the corresponding C12-substituted acetal alcohols. Acid-catalyzed cyclization of these adducts yielded C12,N13-bridged tetrahydrofuran, pyran, and dioxane compounds 10 − 13.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12003530</pmid><doi>10.1021/jo0108360</doi><tpages>7</tpages></addata></record> |
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subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Organic chemistry Preparations and properties |
title | Syntheses of C12,N13 Heterocyclic Bridged Fused Indenopyrrolocarbazoles |
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