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Volumn 69, Issue 10, 2004, Pages 3550-3553

N-Acylazinium Salts: A New Source of Iminium Ions for Ugi-Type Processes

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS; WATER;

EID: 17744403755     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049823n     Document Type: Article
Times cited : (84)

References (36)
  • 10
    • 0003417469 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, Chapter 4
    • (a) Ugi, I.; Lohberger, S.; Karl, R. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 4.
    • (1991) Comprehensive Organic Synthesis , vol.2
    • Ugi, I.1    Lohberger, S.2    Karl, R.3
  • 14
    • 2442515033 scopus 로고
    • (a) Interaction of isocyanides with N-alkylquinolinium salts, takes place with moderate yields, see: Ugi, I.; Boettner, E. Ann. 1983, 670, 74.
    • (1983) Ann. , vol.670 , pp. 74
    • Ugi, I.1    Boettner, E.2
  • 20
    • 0038203081 scopus 로고    scopus 로고
    • (d) For a catalytic asymmetric Passerini-type reaction, see: Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2003, 125, 7825.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 7825
    • Denmark, S.E.1    Fan, Y.2
  • 21
    • 0033551720 scopus 로고    scopus 로고
    • Water efficiently acts as the acid component in Ugi reactions (see refs 4), although this may not be the only outcome for the imidoyl chloride intermediate. For interesting possibilities, see: Livinghouse, T. Tetrahedron 1999, 55, 9947.
    • (1999) Tetrahedron , vol.55 , pp. 9947
    • Livinghouse, T.1
  • 22
    • 2442493835 scopus 로고    scopus 로고
    • note
    • The α-cerboxamido(iso)quinoline motif is frequently found in biologically active compounds, with more than 6800 structures listed in Scifinder, mainly in drug patents.
  • 23
    • 2442479313 scopus 로고
    • 3-catalyzed Reissert reactions on pyridines developed by Popp afforded, in our system, a complex mixture, and modifications of this idea are under study. For relevant references, see: (a) Duarte, F. F.; Popp, F. D.; Holder, A. J. J. Heterocycl. Chem. 1993, 30, 893.
    • (1993) J. Heterocycl. Chem. , vol.30 , pp. 893
    • Duarte, F.F.1    Popp, F.D.2    Holder, A.J.3
  • 29
    • 2442467594 scopus 로고    scopus 로고
    • note
    • 3 catalysis, the corresponding cycloadduct 5a was isolated in 60% yield as a 2:1 mixture of epimers at the ester α-position. Good stereocontrol of the remaining stereogenic centers was observed (see, ref 3c). diagram presented


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.