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Volumn 71, Issue 9, 2006, Pages 3494-3500

Coupling-isomerization - N,S-ketene acetal-addition sequences - A three-component approach to highly fluorescent pyrrolo[2,3-b]pyridines, [1,8]naphthyridines, and pyrido[2,3-b]azepines

Author keywords

[No Author keywords available]

Indexed keywords

ANNEALING; AROMATIZATION; COMPUTATIONAL METHODS; ELECTRONIC STRUCTURE; FLUORESCENCE; X RAY ANALYSIS;

EID: 33646244300     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0602726     Document Type: Article
Times cited : (58)

References (46)
  • 1
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    • Zhu, J., Bienaymé, H., Eds., Wiley-VCH: Weinheim, Germany
    • For a recent monography, see for example: Multicomponent Reactions; Zhu, J., Bienaymé, H., Eds., Wiley-VCH: Weinheim, Germany, 2005.
    • (2005) Multicomponent Reactions
  • 13
    • 0034678033 scopus 로고    scopus 로고
    • (e) Schreiber, S. L. Science 2000, 287, 1964-1969.
    • (2000) Science , vol.287 , pp. 1964-1969
    • Schreiber, S.L.1
  • 16
    • 0002769275 scopus 로고    scopus 로고
    • Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany
    • (b) Sonogashira, K. In Metal Catalyzed Cross-coupling Reactions, Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998, 203-229.
    • (1998) Metal Catalyzed Cross-coupling Reactions , pp. 203-229
    • Sonogashira, K.1
  • 30
    • 85012738894 scopus 로고
    • Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford
    • Boger, D. L.; Patel, M. In Progress in Heterocyclic Chemistry. Suschitzky, H., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1989, Vol. 1.
    • (1989) Progress in Heterocyclic Chemistry , vol.1
    • Boger, D.L.1    Patel, M.2
  • 42
    • 0000730888 scopus 로고
    • The N,S-ketene acetals were synthesized in a three-step sequence starting from the corresponding cyclic amides, according to: Yde, B.; Yousif, N. M.; Pedersen, U.; Thomsen, I.; Lawesson, S.-O. Tetrahedron 1984, 40, 2047-2052. By thionation with Lawesson's reagent, the amides were converted into the thiocarbonyl compounds in excellent yields (85-95%). After methylation with methyl iodide and recrystallisation from acetone, 5-alkylated iodide salts (75-90%) were treated with potassium tert-butoxide to furnish the N,S-ketene acetals in moderate overall yields (35-65%).
    • (1984) Tetrahedron , vol.40 , pp. 2047-2052
    • Yde, B.1    Yousif, N.M.2    Pedersen, U.3    Thomsen, I.4    Lawesson, S.-O.5
  • 43
    • 33646233643 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-297966 (4a), CCDC-297967 (4c), CCDC-297968 (4e), CCDC-297970 (4h), CCDC-297969 (4i). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 IEZ, U.K. (fax: + 44-1223/ 336-033; e-mail: deposit@ccdc.cam.ac.uk).
  • 44
    • 0004127279 scopus 로고    scopus 로고
    • Wavefunction, Inc.: Irvine, CA
    • As implemented in PC Spartan Pro, Wavefunction, Inc.: Irvine, CA, 2002.
    • (2002) PC Spartan Pro


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.