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Volumn 64, Issue 14, 1999, Pages 5132-5138

Reactions of benzocyclic β-keto esters with sulfonyl azides. 2. Further insight into the influence of azide structure and solvent on the reaction course

Author keywords

[No Author keywords available]

Indexed keywords

2 ETHYOXYCARBONYL 1 BENZOSUBERONE; 4 METHOXYBENZENESULFONYL AZIDE; AZIDE; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033039790     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9901541     Document Type: Article
Times cited : (39)

References (26)
  • 3
    • 0000709206 scopus 로고
    • Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley-Interscience: New York, 1998, Chapter 1. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. Regitz, M.; Maas, G. Diazo Compounds: Properties and Synthesis; Academic Press: New York, 1986; Chapter 13.
    • (1994) Chem. Rev. , vol.94 , pp. 1091
    • Ye, T.1    McKervey, M.A.2
  • 4
    • 0004069877 scopus 로고
    • Academic Press: New York, Chapter 13
    • Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley-Interscience: New York, 1998, Chapter 1. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. Regitz, M.; Maas, G. Diazo Compounds: Properties and Synthesis; Academic Press: New York, 1986; Chapter 13.
    • (1986) Diazo Compounds: Properties and Synthesis
    • Regitz, M.1    Maas, G.2
  • 5
    • 84988095462 scopus 로고
    • Lombardo, L.; Mander, L. N. Synthesis 1980, 368. Coates, R. M.; Kang, H.-Y J. Org. Chem. 1987, 52, 2065. Uyehara, T.; Takehara, N.; Ueno, M.; Sato, T. Bull. Chem. Soc. Jpn. 1995, 68, 2687.
    • (1980) Synthesis , pp. 368
    • Lombardo, L.1    Mander, L.N.2
  • 6
    • 0000843905 scopus 로고
    • Lombardo, L.; Mander, L. N. Synthesis 1980, 368. Coates, R. M.; Kang, H.-Y J. Org. Chem. 1987, 52, 2065. Uyehara, T.; Takehara, N.; Ueno, M.; Sato, T. Bull. Chem. Soc. Jpn. 1995, 68, 2687.
    • (1987) J. Org. Chem. , vol.52 , pp. 2065
    • Coates, R.M.1    Kang, H.-Y.2
  • 17
    • 85069282342 scopus 로고    scopus 로고
    • note
    • It is noteworthy that acyclic β-keto esters, contrary to our cyclic counterparts, normally undergo deacylating diazo transfer in preference to azidation and/or Favorskii-type rearrangement, irrespective of the aromatic or aliphatic ketone moiety and the sulfonyl azide reagent. This fact probably arises from comparatively easier production of monocyclic triazolines as well as from higher propensity of such monocyclic intermediates to suffer ring-cleavage fragmentations to diazo compounds.
  • 25
    • 0008079016 scopus 로고
    • Azide 21a had been previously reported, but no spectral data were available: Forster, M. O.; Müller, R. J. Chem. Soc. 1910, 97, 126.
    • (1910) J. Chem. Soc. , vol.97 , pp. 126
    • Forster, M.O.1    Müller, R.2
  • 26
    • 85069277503 scopus 로고    scopus 로고
    • Commercially available (Lancaster)
    • Commercially available (Lancaster).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.