메뉴 건너뛰기




Volumn 39, Issue 14, 2000, Pages 2488-2490

Versatile indole synthesis by a 5-endo-dig cyclization mediated by potassium or cesium bases

Author keywords

Cyclizations; Nitrogen heterocycles; Synthetic methods

Indexed keywords

CESIUM; INDOLE; POTASSIUM;

EID: 0034679471     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000717)39:14<2488::AID-ANIE2488>3.0.CO;2-E     Document Type: Article
Times cited : (236)

References (39)
  • 4
    • 0032486218 scopus 로고    scopus 로고
    • c) J. H. Teles, S. Brode, M. Chabanas, Angew. Chem. 1998, 110, 1475; Angew. Chem. Int. Ed. 1998, 37, 1415;
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1415
  • 7
    • 33947238138 scopus 로고    scopus 로고
    • M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trauthwein, Angew. Chem. 1998, 110, 3571; Angew. Chem. Int. Ed. 1998, 37, 3389;
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 3389
  • 9
    • 0030700582 scopus 로고    scopus 로고
    • b) see also M. Beller, M. Eichberger, H. Trauthwein, Angew. Chem. 1997, 109, 2306; Angew. Chem. Int. Ed. Engl. 1997, 36, 2225;
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2225
  • 13
    • 0033549728 scopus 로고    scopus 로고
    • b) B. Witulski, T. Stengel, Angew. Chem. 1999, 111, 2521; Angew. Chem. Int. Ed. 1999, 38, 2426;
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 2426
  • 21
  • 22
    • 0033577829 scopus 로고    scopus 로고
    • a) D. Tzalis, P. Knochel, Angew. Chem. 1999, 111, 1547; Angew. Chem. Int. Ed. 1999, 38, 1463;
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1463
  • 27
    • 0002103980 scopus 로고
    • The treatment of 1a with NaOEt in boiling ethanol does not lead to the corresponding indole 2a, showing that the use of NMP is essential for the direct cyclization of 1a to 2a; see also: T. Sakamoto, Y. Kondo, H. Yamanaka, Heterocycles 1986, 24, 31.
    • (1986) Heterocycles , vol.24 , pp. 31
    • Sakamoto, T.1    Kondo, Y.2    Yamanaka, H.3
  • 28
    • 84918129478 scopus 로고
    • KOtBu has exceptional basic properties: a) M. Schlosser, Pure Appl. Chem. 1988, 60, 1627; b) M. Schlosser, J. Hartmann, J. Am. Chem. Soc. 1976, 98, 4647; c) M. Schlosser, G. Rauchschwalbe, J. Am. Chem. Soc. 1978, 100, 3258.
    • (1988) Pure Appl. Chem. , vol.60 , pp. 1627
    • Schlosser, M.1
  • 29
    • 84918129478 scopus 로고
    • KOtBu has exceptional basic properties: a) M. Schlosser, Pure Appl. Chem. 1988, 60, 1627; b) M. Schlosser, J. Hartmann, J. Am. Chem. Soc. 1976, 98, 4647; c) M. Schlosser, G. Rauchschwalbe, J. Am. Chem. Soc. 1978, 100, 3258.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 4647
    • Schlosser, M.1    Hartmann, J.2
  • 30
    • 0000760349 scopus 로고
    • KOtBu has exceptional basic properties: a) M. Schlosser, Pure Appl. Chem. 1988, 60, 1627; b) M. Schlosser, J. Hartmann, J. Am. Chem. Soc. 1976, 98, 4647; c) M. Schlosser, G. Rauchschwalbe, J. Am. Chem. Soc. 1978, 100, 3258.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 3258
    • Schlosser, M.1    Rauchschwalbe, G.2
  • 31
    • 0343700297 scopus 로고    scopus 로고
    • Cesium tert-butoxide is conveniently prepared by the addition of tBuOH to cesium in toluene at 0 C (15 min)
    • Cesium tert-butoxide is conveniently prepared by the addition of tBuOH to cesium in toluene at 0 C (15 min).
  • 32
    • 0343700298 scopus 로고    scopus 로고
    • note
    • The suspension of KH in NMP may generate the soluble potassium enolate of N-methylpyrrolidinone. Reaction products derived from this enolate have been isolated in related cyclization reactions.
  • 35
    • 0001439643 scopus 로고    scopus 로고
    • c) A. F. Littke, G. C. Fu, Angew. Chem. 1999, 111, 2568; Angew. Chem. Int. Ed. 1999, 38, 2411.
    • (1999) Angew. Chem. , vol.111 , pp. 2568
    • Littke, A.F.1    Fu, G.C.2
  • 36
    • 0033549832 scopus 로고    scopus 로고
    • c) A. F. Littke, G. C. Fu, Angew. Chem. 1999, 111, 2568; Angew. Chem. Int. Ed. 1999, 38, 2411.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 2411
  • 39
    • 0343264684 scopus 로고    scopus 로고
    • A patent application with the BASF AG has been filed
    • A patent application with the BASF AG has been filed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.