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Volumn 37, Issue 5, 1996, Pages 683-686

Conformationally constrained serotonin analogues: Stereoselective synthesis of trans -3-(2-aminocycloalkyl)indoles by aziridine ring opening

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE;

EID: 0030052741     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02242-2     Document Type: Article
Times cited : (19)

References (27)
  • 1
    • 77950120565 scopus 로고
    • Weissberger, A.; Taylor, E. C., Eds. John Wiley & Sons (III), Chapter VIII
    • Spande, T. F. in The Chemistry of Heterocyclic Compounds. Weissberger, A.; Taylor, E. C., Eds. John Wiley & Sons. 1979, Vol. 25 (III), Chapter VIII.
    • (1979) The Chemistry of Heterocyclic Compounds , vol.2 , pp. 5
    • Spande, T.F.1
  • 5
    • 0029116299 scopus 로고
    • and references cited therein
    • Macor, J. E. Tetrahedron lett. 1995, 36, 7019-7022 and references cited therein.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 7019-7022
    • Macor, J.E.1
  • 11
    • 84867007251 scopus 로고
    • and references cited therein
    • (a) Lygo, B. Synlett 1993, 764-766 and references cited therein.
    • (1993) Synlett , pp. 764-766
    • Lygo, B.1
  • 15
    • 0000315403 scopus 로고
    • The use of SmI2 has shown to be quite effective in these deprotection reactions. Vedejs, E.; Lin, S. J. Org. Chem. 1994, 59, 1602-1603.
    • (1994) J. Org. Chem. , vol.59 , pp. 1602-1603
    • Vedejs, E.1    Lin, S.2
  • 16
    • 0001565241 scopus 로고
    • Urethane activation of aziridines and reaction with indole under Lewis acid catalyst, has been described for the synthesis of different tryptophanes and other derivatives: (a) Sato, K.; Kozikowski A. P. Tetrahedron Lett. 1989, 30, 4073-4076.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 4073-4076
    • Sato, K.1    Kozikowski, A.P.2
  • 24
    • 0343168326 scopus 로고
    • Trost, B. M.; Fleming, I.; Eds. Pergamon, Oxford Chapter 1.4
    • Lipshutz, B. H. in "Comprehensive Organic Synthesis", Trost, B. M.; Fleming, I.; Eds. Pergamon, Oxford 1991; Vol. 1, Chapter 1.4.
    • (1991) Comprehensive Organic Synthesis , vol.1
    • Lipshutz, B.H.1
  • 26
    • 85029987290 scopus 로고    scopus 로고
    • note
    • This compound was prepared by reductive animation as described in ref. 5a
  • 27
    • 85029992786 scopus 로고    scopus 로고
    • note
    • 13C NMR, IR and HRMS) have been obtained for all compounds reported in this communication.


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