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Volumn 61, Issue 26, 2005, Pages 6425-6437

A highly active catalyst for the reductive cyclization of ortho-nitrostyrenes under mild conditions

Author keywords

Nitrostyrene; Palladium; Reductive cyclization

Indexed keywords

3,4,7,8 TETRAMETHYL 1,10 PHENANTHROLINE; INDOLE DERIVATIVE; N,N DIMETHYLFORMAMIDE; PALLADIUM COMPLEX; STYRENE DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

EID: 20444452906     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.03.142     Document Type: Article
Times cited : (90)

References (68)
  • 3
    • 84943388739 scopus 로고
    • Pyrroles and Their Benzoderivatives: Synthesis and Applications
    • A.R. Katritzky C.W. Rees Pergamon Oxford
    • R.J. Sundberg A.R. Katritzky C.W. Rees Pyrroles and Their Benzoderivatives: Synthesis and Applications Comprehensive Heterocyclic Chemistry Vol. 4 1984 Pergamon Oxford 313 376
    • (1984) Comprehensive Heterocyclic Chemistry , vol.4 , pp. 313-376
    • Sundberg, R.J.1
  • 6
    • 0013614138 scopus 로고
    • W.J. Houlihan Wiley New York
    • R.K. Brown W.J. Houlihan Indoles 1972 Wiley New York
    • (1972) Indoles
    • Brown, R.K.1
  • 17
    • 20444502724 scopus 로고    scopus 로고
    • note
    • Ortho-nitrostyrene 3 was synthesized in five steps from readily available starting materials. See Ref. 6b for details.
  • 43
    • 1342332918 scopus 로고    scopus 로고
    • We recently reported the palladium-catalyzed cyclization of ortho-nitrobiphenyl substrates to afford carbazoles using palladium (II) acetate and 1,10-phenanthroline in DMF at 140°C and 70 psig CO: J.H. Smitrovich, and I.W. Davies Org. Lett. 6 2004 533 535
    • (2004) Org. Lett. , vol.6 , pp. 533-535
    • Smitrovich, J.H.1    Davies, I.W.2
  • 45
  • 51
    • 20444435285 scopus 로고    scopus 로고
    • note
    • Osborn et al. have proposed the formation of an analogous palladacycle as the first step in the catalytic cycle for the palladium-catalyzed reduction of nitroaromatics to isocyanates. See Refs. 15a and b.
  • 52
    • 0030700933 scopus 로고    scopus 로고
    • Nitrosoarene-metal complexes have been identified as intermediates in the ruthenium-catalyzed reductive deoxygenation of nitroarenes: S.J. Skoog, and W.L. Gladfelter J. Am. Chem. Soc. 119 1997 11049 11060
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 11049-11060
    • Skoog, S.J.1    Gladfelter, W.L.2
  • 53
    • 0004540113 scopus 로고    scopus 로고
    • ortho-Nitroarylethanes have also been shown to react under basic conditions to give N-hydroxyindoles at 20°C. The reaction was rationalized to proceed through an ortho-nitrosostyrene species that undergoes a 6π-electron 5-atom electrocyclic reaction: Z. Wróbel, and M. Mȩkosza Tetrahedron 53 1997 5501 5514
    • (1997) Tetrahedron , vol.53 , pp. 5501-5514
    • Wróbel, Z.1    Mȩkosza, M.2
  • 55
    • 20444473577 scopus 로고    scopus 로고
    • note
    • While palladium may be involved in the cyclization of 17, calculations reveal that the presence of palladium is not required: Ref. 27.
  • 57
    • 20444467861 scopus 로고    scopus 로고
    • note
    • Ragaini et al. reported reduced yields and conversions for the palladium-catalyzed formation of oxazines from electron rich nitroarenes and 2,3-dimethylbutadiene in the presence of CO: Ref. 17.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.