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Volumn 74, Issue 4, 2009, Pages 1673-1678

Palladium-catalyzed annulation of haloanilines and halobenzamides using norbornadiene as an acetylene synthon: A route to functionalized indolines, isoquinolinones, and indoles

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONALIZED; HALOANILINES; ISOQUINOLINONES; NORBORNADIENE; SUBSTITUTED INDOLES; SYNTHON;

EID: 64349087700     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802604g     Document Type: Article
Times cited : (78)

References (43)
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    • For syntheses of indoles in which the substituents on the benzenoid ring are easily varied, see: a
    • For syntheses of indoles in which the substituents on the benzenoid ring are easily varied, see: (a) Dunetz, J. R.; Danheiser, R. L. J. Am. Chem. Soc. 2005, 127, 5776.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 5776
    • Dunetz, J.R.1    Danheiser, R.L.2
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    • Electron-rich, bulky phosphanes promote aromatic animations: (a) Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413.
    • Electron-rich, bulky phosphanes promote aromatic animations: (a) Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413.
  • 27
    • 0033529898 scopus 로고    scopus 로고
    • For the use of the DavePhos ligand in aminations, see
    • For the use of the DavePhos ligand in aminations, see: Harris, M. C.; Geis, O.; Buchwald, S. L. J. Org. Chem. 1999, 64, 6019.
    • (1999) J. Org. Chem , vol.64 , pp. 6019
    • Harris, M.C.1    Geis, O.2    Buchwald, S.L.3
  • 28
    • 64349100299 scopus 로고    scopus 로고
    • For X-ray crystal data, see the Supporting Information
    • For X-ray crystal data, see the Supporting Information.
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    • This would create a novel two-step approach to indole synthesis. A related method is the Larock indole synthesis, whereby indoles can be produced in one step from o-haloanilines and acetylenes. Larock, R. C, Yum, E. K, Refvik, M. D. J. Org. Chem. 1998, 63, 7652
    • This would create a novel two-step approach to indole synthesis. A related method is the Larock indole synthesis, whereby indoles can be produced in one step from o-haloanilines and acetylenes. Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652.
  • 30
    • 23644461386 scopus 로고    scopus 로고
    • [4 + 2] cycloadditions between indole and cyclopentadiene have been reported: (a) Davies, H. M. L.; Dai, X. J. Org. Chem. 2005, 70, 6680.
    • [4 + 2] cycloadditions between indole and cyclopentadiene have been reported: (a) Davies, H. M. L.; Dai, X. J. Org. Chem. 2005, 70, 6680.
  • 33
    • 64349112651 scopus 로고    scopus 로고
    • For examples of retro-Diels-Alder reactions used to obtain heterocyclic compounds, see: (a) Burgess, K. L, Lajkiewicz, N. J, Sanyal, A, Yan, W, Snyder, J. K. Org. Lett. 2005, 7, 3795
    • For examples of retro-Diels-Alder reactions used to obtain heterocyclic compounds, see: (a) Burgess, K. L.; Lajkiewicz, N. J.; Sanyal, A.; Yan, W.; Snyder, J. K. Org. Lett. 2005, 7, 3795.
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    • International Patent PCT/US2003/012691, 2003
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.