Atom-Economical Synthesis of N-Heterocycles via Cascade Inter-/Intramolecular C—N Bond-Forming Reactions Catalyzed by Ti Amides.
Direct and efficient catalytic reactions with excellent regioselectivity for the preparation of a series of substituted isoindoles, isoquinolines, and imidazoles are reported. Reaction of CH(2-CN)C≡C-R with an array of amines, catalyzed by 10 mol % of [ó:η:η-(OCH)(MeNCH)CBH]Ti(NMe) (1), gives a seri...
| Publicado en: | Journal of the American Chemical Society Vol. 132; no. 33; pp. 11473 - 11481 |
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| Autores principales: | , |
| Formato: | Artículo |
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American Chemical Society
8/25/2010
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| Acceso en línea: | Ver este registro en EBSCOhost |
| fields | @attributes: recordID: 1 pdfLink: plink: https://search.ebscohost.com/login.aspx?direct=true&db=hlh&AN=53380702&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 53380702 longDbName: Humanities International Complete uiTag: AN controlInfo: bkinfo: jinfo: jid: 00027863 ACS jtl: Journal of the American Chemical Society issn: 00027863 maglogo: N pubinfo: dt: 8/25/2010 vid: 132 iid: 33 pid: 997 pub: American Chemical Society artinfo: ui: 53380702 10.1021/ja101796k ppf: 11473 ppct: 8 formats: tig: atl: Atom-Economical Synthesis of N-Heterocycles via Cascade Inter-/Intramolecular C—N Bond-Forming Reactions Catalyzed by Ti Amides. aug: au: Hao Shen Zuowei Xie affil: Department of Chemistry and Center of Novel Functional Molecules, Chinese University of Hong Kong, Shatin, N. T., Hong Kong, China su: Amides Titanium Catalysis Chemical bonds Indole Isoquinoline Amines sug: subj: Amides Titanium Catalysis Chemical bonds Indole Isoquinoline Amines ab: Direct and efficient catalytic reactions with excellent regioselectivity for the preparation of a series of substituted isoindoles, isoquinolines, and imidazoles are reported. Reaction of CH(2-CN)C≡C-R with an array of amines, catalyzed by 10 mol % of [ó:η:η-(OCH)(MeNCH)CBH]Ti(NMe) (1), gives a series of substituted isoindoles in very high yields. In a similar manner, interaction of CH(2-CHCN)C≡C-Ph with various kinds of amines affords a wide range of substituted isoquinolines. On the other hand, treatment of propargylamines (R'C≡CCHNHR") with nitriles in the presence of 10 mol % of 1 produces a class of substituted imidazoles in high yields. A possible reaction mechanism is proposed, involving sequential inter- and intramolecular C-N bond formation via hydroamination/cyclization reaction of cyanoalkynes with amines or nitriles with propargylamines catalyzed by titanium amides. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2010 holdings: @attributes: islocal: N |
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