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Volumn 10, Issue 2, 2008, Pages 313-316

Synthesis of polysubstituted N-H pyrroles from vinyl azides and 1,3-dicarbonyl compounds

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EID: 38749150358     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702727j     Document Type: Article
Times cited : (181)

References (45)
  • 1
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    • Katritzky, A. R, Rees, C. W, Scriven, E. F. V, Eds, Elsevier: Oxford, UK
    • (a) Gribble, G. W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier: Oxford, UK, 1996; Vol. 2, p 207.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.2 , pp. 207
    • Gribble, G.W.1
  • 6
    • 34347271241 scopus 로고    scopus 로고
    • For recent reports on the synthesis of polysubstituted pyrroles, see: a
    • For recent reports on the synthesis of polysubstituted pyrroles, see: (a) Su, S.; Porco, J. A., Jr. J. Am. Chem. Soc. 2007, 129, 7744.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 7744
    • Su, S.1    Porco Jr., J.A.2
  • 30
    • 0000492656 scopus 로고    scopus 로고
    • Palacios, F.; Aparicio, D.; de los Santos, J. M.; Perez de Heredia, I.; Rubiales, G. Org. Prep. Proced. Int. 1995, 27, 171.
    • (c) Palacios, F.; Aparicio, D.; de los Santos, J. M.; Perez de Heredia, I.; Rubiales, G. Org. Prep. Proced. Int. 1995, 27, 171.
  • 31
    • 0008384277 scopus 로고
    • Trost, B. M, Fleming, I, Ley, S, Eds, Pergamon: Oxford
    • (a) Moody, C. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Ley, S., Eds.; Pergamon: Oxford, 1991; Vol. 7, p 21.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 21
    • Moody, C.J.1
  • 37
    • 34250851338 scopus 로고    scopus 로고
    • Recently, Rh(II)-catalyzed indole formation from azidocinnamates was reported, see: Stokes, B. J.; Dong, H.; Lesile, B. E.; Pumphrey, A. L.; Driver, T. G. J. Am. Chem. Soc. 2007, 129, 7500.
    • Recently, Rh(II)-catalyzed indole formation from azidocinnamates was reported, see: Stokes, B. J.; Dong, H.; Lesile, B. E.; Pumphrey, A. L.; Driver, T. G. J. Am. Chem. Soc. 2007, 129, 7500.
  • 38
    • 38749128643 scopus 로고    scopus 로고
    • We examined the following additives; AcOH, PPTS, TfOH, MgBr2, Mg(OTf)2, K2CO3, CuCO3, DABCO, H2O, and MS 4Å
    • 2O, and MS 4Å.
  • 39
    • 38749153136 scopus 로고    scopus 로고
    • The structure of 4a was secured by X-ray crystallographic analysis. CCDC-295066 contains the supplementary crystallographic data for compound 4a. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB21 EZ, UK; fax: (+44)1223-336-033; or e-mail deposit@cdc.cam.ac.uk). See Supporting Information.
    • The structure of 4a was secured by X-ray crystallographic analysis. CCDC-295066 contains the supplementary crystallographic data for compound 4a. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB21 EZ, UK; fax: (+44)1223-336-033; or e-mail deposit@cdc.cam.ac.uk). See Supporting Information.
  • 41
    • 38749106496 scopus 로고    scopus 로고
    • 3CN at 40-60°C.
    • 3CN at 40-60°C.
  • 42
    • 0031655465 scopus 로고    scopus 로고
    • For a report on the coordination of the internal nitrogen of an organic azide with a Cu(II) complex, see: Barz, M.; Herdweck, E.; Thiel, W. R. Angew. Chem., Int. Ed. 1998, 37, 2262.
    • (a) For a report on the coordination of the internal nitrogen of an organic azide with a Cu(II) complex, see: Barz, M.; Herdweck, E.; Thiel, W. R. Angew. Chem., Int. Ed. 1998, 37, 2262.
  • 44
    • 38749143594 scopus 로고    scopus 로고
    • For prior studies on the iminyl radical formation from vinyl azides, see: a
    • For prior studies on the iminyl radical formation from vinyl azides, see: (a) Montevecchi, P. C.; Navacchia, M. L.; Spagnolo, P. J. Org. Chem. 1997, 62, 5864.
    • (1997) J. Org. Chem , vol.62 , pp. 5864
    • Montevecchi, P.C.1    Navacchia, M.L.2    Spagnolo, P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.