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Volumn 74, Issue 17, 2009, Pages 6802-6811

Synthesis of 3-sulfenyl- and 3-selenylindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal alkynes, followed by n-Bu4NI-induced electrophilic cyclization

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYLS; CATALYZED COUPLING; CHEMICAL EQUATIONS; ELECTROPHILIC CYCLIZATION; TERMINAL ALKYNE; TWO-STEP PROCESS;

EID: 69549110385     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9014003     Document Type: Article
Times cited : (110)

References (92)
  • 8
    • 69549152911 scopus 로고    scopus 로고
    • PCT Int. Appl. WO 2008012511
    • Armer, R. E.; Wynne, G. M. PCT Int. Appl. WO 2008012511, 2008.
    • (2008)
    • Armer, R.E.1    Wynne, G.M.2
  • 25
    • 0027404530 scopus 로고
    • For early studies on electrophilic cyclization reaction, see (a)
    • For early studies on electrophilic cyclization reaction, see (a) Ren, X.-F.; Turos, E. Tetrahedron Lett. 1993, 34, 1575.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 1575
    • Ren, X.-F.1    Turos, E.2
  • 78
    • 0002769275 scopus 로고    scopus 로고
    • Diederich, F., Stang, P. J., Eds.; Wiley-VCH:Weinheim, Germany
    • (a) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH:Weinheim, Germany, 1998; pp 203.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions , pp. 203
    • Sonogashira, K.1
  • 80
    • 69549145128 scopus 로고    scopus 로고
    • note
    • The N,N-dialkyl-ortho-iodoanilines have been prepared by the dialkylation reaction. The detailed results are summarized in the Supporting Information.
  • 81
    • 69549142020 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of the reaction mixture indicated that no cyclized indole product was formed.
  • 85
    • 69549141201 scopus 로고    scopus 로고
    • note
    • About 15% of 1-benzyl-5-bromo-2-(4-methoxy-phenyl)indole was obtained alongside the desired cyclized product 5bg when this Sonogashira coupling was carried out under the reaction conditions described in Table 1.
  • 87
    • 69549132769 scopus 로고    scopus 로고
    • note
    • For an example of the preparation and characterization of a 3-iodoindolium triiodide species, see ref 19d.
  • 88
    • 69549144295 scopus 로고    scopus 로고
    • note
    • We have been able to observe MeBr and the analogous selenium intermediate in our synthesis of benzoselenophenes. See ref 23a.
  • 89
    • 0035898871 scopus 로고    scopus 로고
    • For a selected example of the synthesis and reactivity of an arylsulfenyl iodide, see
    • For a selected example of the synthesis and reactivity of an arylsulfenyl iodide, see Goto, K.; Yamamoto, G.; Tan, B.; Okazaki, R. Tetrahedron Lett. 2001, 42, 4875.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 4875
    • Goto, K.1    Yamamoto, G.2    Tan, B.3    Okazaki, R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.