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Volumn 9, Issue 22, 2011, Pages 7780-7790

A one-pot synthesis of 7-phenylindolo[3,2-a]carbazoles from indoles and β-nitrostyrenes, via an unprecedented reaction sequence

Author keywords

[No Author keywords available]

Indexed keywords

CONJUGATE ADDITION; GOOD YIELD; HETEROCYCLES; NITROSTYRENE; ONE-POT REACTION; ONE-POT SYNTHESIS; REACTION SEQUENCES; REGIO-SELECTIVE;

EID: 80054993985     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c1ob06108a     Document Type: Article
Times cited : (40)

References (34)
  • 22
    • 0027453793 scopus 로고
    • 3,3′-Trimer can be conveniently prepared by treatment of 1H-indole 9a with dilute aqueous HCl (See ref. 9c and 14)
    • J. Lehmann N. Jiang A. Behncke Arch. Pharm. 1993 326 813
    • (1993) Arch. Pharm. , vol.326 , pp. 813
    • Lehmann, J.1    Jiang, N.2    Behncke, A.3
  • 24
    • 0342830468 scopus 로고
    • 2O in the conjugated Friedel-Crafts reaction between 1H-indole 9a and nitrostyrene 8b. Reactions were carried out either at room temperature in various solvents or in refluxing dichloromethane and always failed to proceed
    • G. F. Smith Chem. Ind. (London) 1954 1451
    • (1954) Chem. Ind. (London) , vol.6 , pp. 1451
    • Smith, G.F.1
  • 28
    • 77649272768 scopus 로고    scopus 로고
    • 2O (at least two molar equivalents) is known to reduce nitroolefins into the corresponding oxime. In the commonly accepted mechanism, the first step involves a two-electron reduction of the nitro olefin into the nitroso olefin. When the reaction is performed in nucleophilic solvents such as alcohols and thiols, and in the presence of stoichiometric amount of the reducing agent, the highly reactive nitroso olefin intermediate could be trapped leading to the corresponding α-alkoxy (or thioalkoxy) oxime (See ref. 27). For a detailed description of the mechanism for the reduction of nitroolefin into oxime, see ref. 28
    • P. Li M. M. Majireck J. A. Witek S. M. Weinreb Tetrahedron Lett. 2010 51 2032
    • (2010) Tetrahedron Lett. , vol.51 , pp. 2032
    • Li, P.1    Majireck, M.M.2    Witek, J.A.3    Weinreb, S.M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.