Synthesis of Isoquinolines and Heterocycle-Fused Pyridines via Three-Component Cascade Reaction of Aryl Ketones, Hydroxylamine, and Alkynes
An efficient one-pot synthesis of isoquinolines and heterocycle-fused pyridines by three-component reaction of aryl ketones, hydroxylamine, and alkynes is developed. The reaction involves condensation of aryl ketones and hydroxylamine, rhodium(III)-catalyzed C–H bond activation of the in situ genera...
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| Veröffentlicht in: | Journal of organic chemistry 2012-07, Vol.77 (13), p.5794-5800 |
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| container_end_page | 5800 |
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| container_issue | 13 |
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| container_title | Journal of organic chemistry |
| container_volume | 77 |
| creator | Zheng, Liyao Ju, Jia Bin, Yunhui Hua, Ruimao |
| description | An efficient one-pot synthesis of isoquinolines and heterocycle-fused pyridines by three-component reaction of aryl ketones, hydroxylamine, and alkynes is developed. The reaction involves condensation of aryl ketones and hydroxylamine, rhodium(III)-catalyzed C–H bond activation of the in situ generated aryl ketone oximes, and cyclization with internal alkynes. This protocol enables rapid assembly of multisubstituted isoquinolines as well as γ-carbolines, furo[2,3-c]pyridines, thieno[2,3-c]pyridines, and benzofuro[2,3-c]pyridines from readily available substrates. |
| doi_str_mv | 10.1021/jo3010414 |
| format | Article |
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The reaction involves condensation of aryl ketones and hydroxylamine, rhodium(III)-catalyzed C–H bond activation of the in situ generated aryl ketone oximes, and cyclization with internal alkynes. This protocol enables rapid assembly of multisubstituted isoquinolines as well as γ-carbolines, furo[2,3-c]pyridines, thieno[2,3-c]pyridines, and benzofuro[2,3-c]pyridines from readily available substrates.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo3010414</identifier><identifier>PMID: 22702218</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alkynes - chemistry ; Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic Compounds - chemical synthesis ; Heterocyclic Compounds - chemistry ; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Hydroxylamine - chemistry ; Isoquinolines - chemical synthesis ; Isoquinolines - chemistry ; Ketones - chemistry ; Molecular Structure ; Organic chemistry ; Preparations and properties ; Pyridines - chemical synthesis ; Pyridines - chemistry ; Stereoisomerism</subject><ispartof>Journal of organic chemistry, 2012-07, Vol.77 (13), p.5794-5800</ispartof><rights>Copyright © 2012 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a411t-ed291476655902dd73fbe88f24cc6fa5a2ca3dfc3c7e7b5d2e5c1fe9339fcad63</citedby><cites>FETCH-LOGICAL-a411t-ed291476655902dd73fbe88f24cc6fa5a2ca3dfc3c7e7b5d2e5c1fe9339fcad63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo3010414$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo3010414$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26132599$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22702218$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zheng, Liyao</creatorcontrib><creatorcontrib>Ju, Jia</creatorcontrib><creatorcontrib>Bin, Yunhui</creatorcontrib><creatorcontrib>Hua, Ruimao</creatorcontrib><title>Synthesis of Isoquinolines and Heterocycle-Fused Pyridines via Three-Component Cascade Reaction of Aryl Ketones, Hydroxylamine, and Alkynes</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>An efficient one-pot synthesis of isoquinolines and heterocycle-fused pyridines by three-component reaction of aryl ketones, hydroxylamine, and alkynes is developed. The reaction involves condensation of aryl ketones and hydroxylamine, rhodium(III)-catalyzed C–H bond activation of the in situ generated aryl ketone oximes, and cyclization with internal alkynes. This protocol enables rapid assembly of multisubstituted isoquinolines as well as γ-carbolines, furo[2,3-c]pyridines, thieno[2,3-c]pyridines, and benzofuro[2,3-c]pyridines from readily available substrates.</description><subject>Alkynes - chemistry</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic Compounds - chemical synthesis</subject><subject>Heterocyclic Compounds - chemistry</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Hydroxylamine - chemistry</subject><subject>Isoquinolines - chemical synthesis</subject><subject>Isoquinolines - chemistry</subject><subject>Ketones - chemistry</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Pyridines - chemical synthesis</subject><subject>Pyridines - chemistry</subject><subject>Stereoisomerism</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>eNptkM1uEzEURi0EoqGw4AWQN0ggdcA_45l4GUWUVFQCQVlHjn2tunjs4DuDmGfgpXHa0G64Gy--o3OvP0JecvaOM8Hf32TJOGt5-4gsuBKs6TRrH5MFY0I0UnTyhDxDvGF1lFJPyYkQfY34ckH-fJvTeA0YkGZPLzD_nELKMSRAapKjGxihZDvbCM35hODol7kEd5v_CoZeXReAZp2HfU6QRro2aI0D-hWMHUNOB-uqzJF-grESeEY3syv59xzNUCVnt0tW8cdcs-fkiTcR4cXxPSXfzz9crTfN5eePF-vVZWNazscGnNC87btOKc2Ec730O1guvWit7bxRRlgjnbfS9tDvlBOgLPegpdS-3tbJU_Lmzrsv9buA43YIaCFGkyBPuK2dtkxXv67o2zvUloxYwG_3JQymzBU6cHx7331lXx21024Ad0_-K7sCr4_AoaToi0k24APXcSmU1g-csVj9U0m1jf8s_AsCjJmx</recordid><startdate>20120706</startdate><enddate>20120706</enddate><creator>Zheng, Liyao</creator><creator>Ju, Jia</creator><creator>Bin, Yunhui</creator><creator>Hua, Ruimao</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>20120706</creationdate><title>Synthesis of Isoquinolines and Heterocycle-Fused Pyridines via Three-Component Cascade Reaction of Aryl Ketones, Hydroxylamine, and Alkynes</title><author>Zheng, Liyao ; Ju, Jia ; Bin, Yunhui ; Hua, Ruimao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a411t-ed291476655902dd73fbe88f24cc6fa5a2ca3dfc3c7e7b5d2e5c1fe9339fcad63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Alkynes - chemistry</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic Compounds - chemical synthesis</topic><topic>Heterocyclic Compounds - chemistry</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Hydroxylamine - chemistry</topic><topic>Isoquinolines - chemical synthesis</topic><topic>Isoquinolines - chemistry</topic><topic>Ketones - chemistry</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Pyridines - chemical synthesis</topic><topic>Pyridines - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zheng, Liyao</creatorcontrib><creatorcontrib>Ju, Jia</creatorcontrib><creatorcontrib>Bin, Yunhui</creatorcontrib><creatorcontrib>Hua, Ruimao</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>Zheng, Liyao</au><au>Ju, Jia</au><au>Bin, Yunhui</au><au>Hua, Ruimao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Isoquinolines and Heterocycle-Fused Pyridines via Three-Component Cascade Reaction of Aryl Ketones, Hydroxylamine, and Alkynes</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2012-07-06</date><risdate>2012</risdate><volume>77</volume><issue>13</issue><spage>5794</spage><epage>5800</epage><pages>5794-5800</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>An efficient one-pot synthesis of isoquinolines and heterocycle-fused pyridines by three-component reaction of aryl ketones, hydroxylamine, and alkynes is developed. The reaction involves condensation of aryl ketones and hydroxylamine, rhodium(III)-catalyzed C–H bond activation of the in situ generated aryl ketone oximes, and cyclization with internal alkynes. This protocol enables rapid assembly of multisubstituted isoquinolines as well as γ-carbolines, furo[2,3-c]pyridines, thieno[2,3-c]pyridines, and benzofuro[2,3-c]pyridines from readily available substrates.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>22702218</pmid><doi>10.1021/jo3010414</doi><tpages>7</tpages></addata></record> |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Alkynes - chemistry Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Hydroxylamine - chemistry Isoquinolines - chemical synthesis Isoquinolines - chemistry Ketones - chemistry Molecular Structure Organic chemistry Preparations and properties Pyridines - chemical synthesis Pyridines - chemistry Stereoisomerism |
| title | Synthesis of Isoquinolines and Heterocycle-Fused Pyridines via Three-Component Cascade Reaction of Aryl Ketones, Hydroxylamine, and Alkynes |
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