A Method for the Synthesis of Substituted Quinolines via Electrophilic Cyclization of 1-Azido-2-(2-propynyl)benzene
A new and efficient strategy for the synthesis of substituted quinolines via electrophilic cyclization is developed. The intramolecular cyclization of 1-azido-2-(2-propynyl)benzene 1 proceeds smoothly in the presence of electrophilic reagents (I2, Br2, ICl, NBS, NIS, and HNTf2) in CH3NO2 at room tem...
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| Veröffentlicht in: | Journal of organic chemistry 2010-02, Vol.75 (4), p.1266-1270 |
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| container_end_page | 1270 |
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| container_issue | 4 |
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| container_title | Journal of organic chemistry |
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| creator | Huo, Zhibao Gridnev, Ilya D Yamamoto, Yoshinori |
| description | A new and efficient strategy for the synthesis of substituted quinolines via electrophilic cyclization is developed. The intramolecular cyclization of 1-azido-2-(2-propynyl)benzene 1 proceeds smoothly in the presence of electrophilic reagents (I2, Br2, ICl, NBS, NIS, and HNTf2) in CH3NO2 at room temperature or in the presence of catalytic amounts of AuCl3/AgNTf2 in THF at 100 °C to afford the corresponding quinolines 2 in good to high yields. In the case of the electrophilic reagents, E of 2 is either I, Br, or H, depending on the reagent type, while E of 2 is H in the case of the electrophilic catalyst. |
| doi_str_mv | 10.1021/jo902603v |
| format | Article |
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The intramolecular cyclization of 1-azido-2-(2-propynyl)benzene 1 proceeds smoothly in the presence of electrophilic reagents (I2, Br2, ICl, NBS, NIS, and HNTf2) in CH3NO2 at room temperature or in the presence of catalytic amounts of AuCl3/AgNTf2 in THF at 100 °C to afford the corresponding quinolines 2 in good to high yields. In the case of the electrophilic reagents, E of 2 is either I, Br, or H, depending on the reagent type, while E of 2 is H in the case of the electrophilic catalyst.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo902603v</identifier><identifier>PMID: 20099928</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Azides - chemistry ; Benzene Derivatives - chemistry ; Catalysis ; Catalysts: preparations and properties ; Chemistry ; Cyclization ; Electrons ; Exact sciences and technology ; General and physical chemistry ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Indicators and Reagents - chemistry ; Molecular Structure ; Noncondensed benzenic compounds ; Organic chemistry ; Preparations and properties ; Quinolines - chemical synthesis ; Quinolines - chemistry ; Solvents - chemistry ; Stereoisomerism ; Theory of reactions, general kinetics. 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Org. Chem</addtitle><description>A new and efficient strategy for the synthesis of substituted quinolines via electrophilic cyclization is developed. The intramolecular cyclization of 1-azido-2-(2-propynyl)benzene 1 proceeds smoothly in the presence of electrophilic reagents (I2, Br2, ICl, NBS, NIS, and HNTf2) in CH3NO2 at room temperature or in the presence of catalytic amounts of AuCl3/AgNTf2 in THF at 100 °C to afford the corresponding quinolines 2 in good to high yields. In the case of the electrophilic reagents, E of 2 is either I, Br, or H, depending on the reagent type, while E of 2 is H in the case of the electrophilic catalyst.</description><subject>Azides - chemistry</subject><subject>Benzene Derivatives - chemistry</subject><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemistry</subject><subject>Cyclization</subject><subject>Electrons</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Indicators and Reagents - chemistry</subject><subject>Molecular Structure</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Quinolines - chemical synthesis</subject><subject>Quinolines - chemistry</subject><subject>Solvents - chemistry</subject><subject>Stereoisomerism</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E1v1DAQBmALgehSOPAHkC-o9GAYj5NsclytyodUhFDhHDnOWOvKay-xUyn763HVpb1gH8aWHs9YL2NvJXyUgPLTbewAG1B3z9hK1gii6aB6zlYAiEJho87Yq5Ruoay6rl-yMwToug7bFUsb_p3yLo7cxonnHfGbJZSSXOLR8pt5SNnlOdPIf84uRO8CJX7nNL_yZPIUDzvnneHbxXh31NnFcP9Ois3RjVGg-IDiUNQSFn85UDhSoNfshdU-0ZtTPWe_P1_92n4V1z--fNturoWuJGSh63awFrsGWol2GOWaEAdosCVpyg1VYxvCCmRlba3KoR5bY8a2aq0lkOqcXTz0LR_4M1PK_d4lQ97rQHFO_VqpWq3LLvLyQZoppjSR7Q-T2-tp6SX09xH3jxEX--7UdR72ND7Kf5kW8P4EdDLa20kH49KTw6qgbv3ktEml_zyFEsZ_Bv4FzsqPgQ</recordid><startdate>20100219</startdate><enddate>20100219</enddate><creator>Huo, Zhibao</creator><creator>Gridnev, Ilya D</creator><creator>Yamamoto, Yoshinori</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>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20100219</creationdate><title>A Method for the Synthesis of Substituted Quinolines via Electrophilic Cyclization of 1-Azido-2-(2-propynyl)benzene</title><author>Huo, Zhibao ; Gridnev, Ilya D ; Yamamoto, Yoshinori</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a410t-a58bff2960812fbd17e22b0628e1cd17236f6e24014ff532405d8ccd848ffe013</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Azides - chemistry</topic><topic>Benzene Derivatives - chemistry</topic><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Chemistry</topic><topic>Cyclization</topic><topic>Electrons</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Indicators and Reagents - chemistry</topic><topic>Molecular Structure</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Quinolines - chemical synthesis</topic><topic>Quinolines - chemistry</topic><topic>Solvents - chemistry</topic><topic>Stereoisomerism</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huo, Zhibao</creatorcontrib><creatorcontrib>Gridnev, Ilya D</creatorcontrib><creatorcontrib>Yamamoto, Yoshinori</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>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>Huo, Zhibao</au><au>Gridnev, Ilya D</au><au>Yamamoto, Yoshinori</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Method for the Synthesis of Substituted Quinolines via Electrophilic Cyclization of 1-Azido-2-(2-propynyl)benzene</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2010-02-19</date><risdate>2010</risdate><volume>75</volume><issue>4</issue><spage>1266</spage><epage>1270</epage><pages>1266-1270</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A new and efficient strategy for the synthesis of substituted quinolines via electrophilic cyclization is developed. The intramolecular cyclization of 1-azido-2-(2-propynyl)benzene 1 proceeds smoothly in the presence of electrophilic reagents (I2, Br2, ICl, NBS, NIS, and HNTf2) in CH3NO2 at room temperature or in the presence of catalytic amounts of AuCl3/AgNTf2 in THF at 100 °C to afford the corresponding quinolines 2 in good to high yields. In the case of the electrophilic reagents, E of 2 is either I, Br, or H, depending on the reagent type, while E of 2 is H in the case of the electrophilic catalyst.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>20099928</pmid><doi>10.1021/jo902603v</doi><tpages>5</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2010-02, Vol.75 (4), p.1266-1270 |
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| subjects | Azides - chemistry Benzene Derivatives - chemistry Catalysis Catalysts: preparations and properties Chemistry Cyclization Electrons Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Indicators and Reagents - chemistry Molecular Structure Noncondensed benzenic compounds Organic chemistry Preparations and properties Quinolines - chemical synthesis Quinolines - chemistry Solvents - chemistry Stereoisomerism Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | A Method for the Synthesis of Substituted Quinolines via Electrophilic Cyclization of 1-Azido-2-(2-propynyl)benzene |
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