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Volumn 124, Issue 40, 2002, Pages 11940-11945

Synthesis of allyl cyanamides and N-cyanoindoles via the palladium-catalyzed three-component coupling reaction

Author keywords

[No Author keywords available]

Indexed keywords

COUPLING REACTION;

EID: 0037048708     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0272742     Document Type: Article
Times cited : (144)

References (84)
  • 1
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    • Hagemann H., Ed.; Georg Thieme Verlag, Stuttgart
    • (a) Lantzsch, R. In Methoden der Organischen Chemie (Houben-Weyl): Hagemann, H., Ed.; Georg Thieme Verlag: Stuttgart, 1983; Vol. E4, pp 974-999.
    • (1983) Methoden der Organischen Chemie (Houben-Weyl) , vol.E4 , pp. 974-999
    • Lantzsch, R.1
  • 17
    • 0032480983 scopus 로고    scopus 로고
    • Palladium-catalyzed synthesis of cyanamides, see: (a) Cerezo, S.; Cortés, J.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869-14884. (b) Cerezo, S.; Cortés, J.; López-Romero, J.-M.; Moreno-Mañas, M.; Parella, T.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14885-14904.
    • (1998) Tetrahedron , vol.54 , pp. 14869-14884
    • Cerezo, S.1    Cortés, J.2    Moreno-Mañas, M.3    Pleixats, R.4    Roglans, A.5
  • 53
    • 0000819379 scopus 로고    scopus 로고
    • Palladium-mediated cyclization from isocyanides(a) Onitsuka, K.; Segawa, M.; Takahashi, S. Organometallics 1998, 17, 4335-4337. (b) Onitsuka, K.; Yamamoto, M.; Suzuki, S.; Takahashi, S. Organometallics 2002, 21, 581-583. During the preparation of the manuscript, the palladium-catalyzed indole synthesis from some isocyanides was reported, see: (a) Suzuki, S.; Yamamoto, M.; Onitsuka, K.; Takahashi, S. Presented at the 81st Annual Meetings of the Chemical Society of Japan, Tokyo, March 2002, Abstract 3G6-28.
    • (1998) Organometallics , vol.17 , pp. 4335-4337
    • Onitsuka, K.1    Segawa, M.2    Takahashi, S.3
  • 54
    • 0000131370 scopus 로고    scopus 로고
    • Palladium-mediated cyclization from isocyanides(a) Onitsuka, K.; Segawa, M.; Takahashi, S. Organometallics 1998, 17, 4335-4337. (b) Onitsuka, K.; Yamamoto, M.; Suzuki, S.; Takahashi, S. Organometallics 2002, 21, 581-583. During the preparation of the manuscript, the palladium-catalyzed indole synthesis from some isocyanides was reported, see: (a) Suzuki, S.; Yamamoto, M.; Onitsuka, K.; Takahashi, S. Presented at the 81st Annual Meetings of the Chemical Society of Japan, Tokyo, March 2002, Abstract 3G6-28.
    • (2002) Organometallics , vol.21 , pp. 581-583
    • Onitsuka, K.1    Yamamoto, M.2    Suzuki, S.3    Takahashi, S.4
  • 55
    • 2142721983 scopus 로고    scopus 로고
    • Chemical Society of Japan, Tokyo, March, Abstract 3G6-28
    • During the preparation of the manuscript, the palladium-catalyzed indole synthesis from some isocyanides was reported, see: (a) Suzuki, S.; Yamamoto, M.; Onitsuka, K.; Takahashi, S. Presented at the 81st Annual Meetings of the Chemical Society of Japan, Tokyo, March 2002, Abstract 3G6-28.
    • (2002) 81st Annual Meetings
    • Suzuki, S.1    Yamamoto, M.2    Onitsuka, K.3    Takahashi, S.4
  • 56
    • 2142738531 scopus 로고    scopus 로고
    • note
    • 3.
  • 60
    • 2142727045 scopus 로고    scopus 로고
    • note
    • The reaction with 2 equiv of allyl methyl carbonate and 2 equiv of trimethylsilyl azide gave 4i only in 37% yield.
  • 61
    • 2142679088 scopus 로고    scopus 로고
    • note
    • These isocyanides were especially unstable in concentrated pure form. Thus, careful handling is needed. See Experimental Section.
  • 77
    • 2142848353 scopus 로고    scopus 로고
    • note
    • Two palladium atoms might participate in this step.
  • 79
    • 0037736344 scopus 로고    scopus 로고
    • Wiley, New York, Chapter 4
    • 2, etc.). However, to the best of our knowledge, there is no report for the oxidative addition of Pd(0) to allyl carbodiimide (Y: N=C=NR). See: Tsuji, J. Transition Metal Reagents and Catalysts; Wiley: New York, 2000; Chapter 4.
    • (2000) Transition Metal Reagents and Catalysts
    • Tsuji, T.1
  • 81
    • 0001242798 scopus 로고    scopus 로고
    • Palladium-catalyzed synthesis of 3-allylindoles, see: (a) Cacchi, S.; Fabrizi, G.; Pace, P. J. Org. Chem. 1998, 63, 1001-1011. (b) Iritani, K.; Matsubara, S.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1799-1802.
    • (1998) J. Org. Chem. , vol.63 , pp. 1001-1011
    • Cacchi, S.1    Fabrizi, G.2    Pace, P.3
  • 82
    • 0001628407 scopus 로고
    • Palladium-catalyzed synthesis of 3-allylindoles, see: (a) Cacchi, S.; Fabrizi, G.; Pace, P. J. Org. Chem. 1998, 63, 1001-1011. (b) Iritani, K.; Matsubara, S.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1799-1802.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 1799-1802
    • Iritani, K.1    Matsubara, S.2    Utimoto, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.