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Volumn , Issue 2, 1998, Pages 105-114

Nitrogen heterocycles from furans: The Aza-Achmatowicz reaction

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EID: 0001381255     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1584     Document Type: Article
Times cited : (145)

References (98)
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    • Trost, B. M.; Hutchinson, C. R., Eds.; Pergamon Press: Oxford, U.K.
    • (a) Achmatowicz, O., in: Organic Synthesis Today and Tomorrow; Trost, B. M.; Hutchinson, C. R., Eds.; Pergamon Press: Oxford, U.K., 1981, p. 307;
    • (1981) Organic Synthesis Today and Tomorrow , pp. 307
    • Achmatowicz, O.1
  • 11
    • 0029988590 scopus 로고    scopus 로고
    • It now appears that oxidation of 6 to 7 may be effected if the furylamine is blocked as a sulfonamide: cf. Xu, Y. M.; Zhou, W. S. Tetrahedron Lett. 1996, 37, 1461, and references cited therein.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 1461
    • Xu, Y.M.1    Zhou, W.S.2
  • 13
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    • note
    • The structure of 14a was ascertained by X-ray crystallography. We are grateful to our colleague, Prof. K. H. Whitmire, for his invaluable assistance with all diffractometric investigations described in this Account.
  • 28
    • 26844575962 scopus 로고    scopus 로고
    • note
    • This reagent was developed by Prof. T. Fukuyama, formerly of this Department. We thank Prof. Fukuyama for sharing with us details of the preparation and use of QCS.
  • 38
    • 26844572619 scopus 로고
    • Dissertation, Rice University
    • Results described in this Section, and for which no literature references are provided, constitute unpublished observations from these laboratories. A preliminary account of several of these observations may be found in: Hermann, C. Y. W. Dissertation, Rice University, 1990.
    • (1990)
    • Hermann, C.Y.W.1
  • 49
    • 26844474697 scopus 로고    scopus 로고
    • note
    • A benzyl carbamate also relieved these difficulties, but it resulted in severe broadening of the NMR spectra of the products (slowly interconverting rotamers).
  • 55
    • 85012099807 scopus 로고
    • An improved procedure for the preparation of the previously known compound 81 is offered in: Xi, N.; Ciufolini, M. A. Tetrahedron Lett. 1995, 36, 6595.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 6595
    • Xi, N.1    Ciufolini, M.A.2
  • 56
    • 26844581322 scopus 로고    scopus 로고
    • note
    • 3, which induced baseline resolution of the methoxy resonances in the spectrum of (±)-14a. Integration of the shifted spectrum of scalemic materials indicated an enantiomer ratio of no less than 96:4, corresponding to at least 92% ee.
  • 75
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    • Harvard University Press: Cambridge, MA
    • (b) Nichols, E. K. Mobilizing Against AIDS; Harvard University Press: Cambridge, MA, 1989.
    • (1989) Mobilizing Against AIDS
    • Nichols, E.K.1
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    • 26844577675 scopus 로고    scopus 로고
    • note
    • The ratio of olefin to enamide thus produced depends on the polarity of the solvent used. This ratio increased from 1:1 in plain THF to 2:1 in 2:1 toluene/THF.
  • 85
    • 0001541420 scopus 로고
    • These eliminations tend to occur away from heteroatoms: Rueger, H.; Benn, M.H. Can. J. Chem. 1982, 60, 2918.
    • (1982) Can. J. Chem. , vol.60 , pp. 2918
    • Rueger, H.1    Benn, M.H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.