Regioselective De Novo Synthesis of Cyanohydroxypyridines with a Concerted Cycloaddition Mechanism
An efficient cycloaddition reaction of 1-alkoxy-1-azadienes with α,α-dicyanoalkenes is described, which gives facile access to highly substituted 3-hydroxypyridines in very good yields and with complete regiocontrol and chemoselectivity. The reaction path was investigated in detail by quantum mechan...
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| Veröffentlicht in: | Journal of the American Chemical Society 2008-10, Vol.130 (40), p.13219-13221 |
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| container_end_page | 13221 |
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| container_issue | 40 |
| container_start_page | 13219 |
| container_title | Journal of the American Chemical Society |
| container_volume | 130 |
| creator | Lu, Jin-Yong Keith, John A Shen, Wei-Zheng Schürmann, Markus Preut, Hans Jacob, Timo Arndt, Hans-Dieter |
| description | An efficient cycloaddition reaction of 1-alkoxy-1-azadienes with α,α-dicyanoalkenes is described, which gives facile access to highly substituted 3-hydroxypyridines in very good yields and with complete regiocontrol and chemoselectivity. The reaction path was investigated in detail by quantum mechanics calculations, reporting that a concerted cycloaddition mechanism and thermodynamic control synergistically contribute to the observed selectivity. |
| doi_str_mv | 10.1021/ja804078v |
| format | Article |
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The reaction path was investigated in detail by quantum mechanics calculations, reporting that a concerted cycloaddition mechanism and thermodynamic control synergistically contribute to the observed selectivity.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja804078v</identifier><identifier>PMID: 18783223</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkenes - chemistry ; Aza Compounds - chemistry ; Cyanides - chemistry ; Cyclization ; Models, Molecular ; Molecular Structure ; Pyridines - chemical synthesis ; Pyridines - chemistry</subject><ispartof>Journal of the American Chemical Society, 2008-10, Vol.130 (40), p.13219-13221</ispartof><rights>Copyright © 2008 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a351t-4548a8b6d690b2448a9c6b7cc5391703a1e191b562097d6f606eff3400d2cc4e3</citedby><cites>FETCH-LOGICAL-a351t-4548a8b6d690b2448a9c6b7cc5391703a1e191b562097d6f606eff3400d2cc4e3</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/ja804078v$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja804078v$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18783223$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lu, Jin-Yong</creatorcontrib><creatorcontrib>Keith, John A</creatorcontrib><creatorcontrib>Shen, Wei-Zheng</creatorcontrib><creatorcontrib>Schürmann, Markus</creatorcontrib><creatorcontrib>Preut, Hans</creatorcontrib><creatorcontrib>Jacob, Timo</creatorcontrib><creatorcontrib>Arndt, Hans-Dieter</creatorcontrib><title>Regioselective De Novo Synthesis of Cyanohydroxypyridines with a Concerted Cycloaddition Mechanism</title><title>Journal of the American Chemical Society</title><addtitle>J. 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| ispartof | Journal of the American Chemical Society, 2008-10, Vol.130 (40), p.13219-13221 |
| issn | 0002-7863 1520-5126 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Alkenes - chemistry Aza Compounds - chemistry Cyanides - chemistry Cyclization Models, Molecular Molecular Structure Pyridines - chemical synthesis Pyridines - chemistry |
| title | Regioselective De Novo Synthesis of Cyanohydroxypyridines with a Concerted Cycloaddition Mechanism |
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