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Volumn 47, Issue 14, 1982, Pages 2765-2768

Oxidative N-Dearylation of 2-Azetidinones. p-Anisidine as a Source of Azetidinone Nitrogen

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE;

EID: 0019932198     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00135a016     Document Type: Article
Times cited : (303)

References (31)
  • 4
    • 85022240750 scopus 로고
    • Preliminary accounts of this work have been published. See:, Belgian Patent 887-428
    • Preliminary accounts of this work have been published. See: Sykes, R. B., et al. Belgian Patent 887-428, 1980.
    • (1980)
    • Sykes, R.B.1
  • 5
    • 0009268666 scopus 로고
    • The persulfate-mediated demethylation of amides is well-known. See
    • The persulfate-mediated demethylation of amides is well-known. See: Needles, H. L.; Whitfield, R. E. J. Org. Chem. 1964, 29, 3632.
    • (1964) J. Org. Chem. , vol.29 , pp. 3632
    • Needles, H.L.1    Whitfield, R.E.2
  • 7
    • 85022291020 scopus 로고
    • Chem. Abstr. 1979, 92, 654.
    • (1979) Chem. Abstr. , vol.92 , pp. 654
  • 10
    • 84918663482 scopus 로고
    • Bose has reported the debenzylation of N-(3,4-dimethoxybenzyl)-azetidinones with persulfate in low yields (21–35%). See ref 7 and: (a)
    • Bose has reported the debenzylation of N-(3,4-dimethoxybenzyl)-azetidinones with persulfate in low yields (21–35%). See ref 7 and: (a) Bose, A. K., et al. Tetrahedron Lett. 1979, 2271.
    • (1979) Tetrahedron Lett. , pp. 2271
    • Bose, A.K.1
  • 12
    • 0019468666 scopus 로고
    • For a recent review see
    • For a recent review see: Bose, A. K., et al. Tetrahedron 1981, 37, 2321.
    • (1981) Tetrahedron , vol.37 , pp. 2321
    • Bose, A.K.1
  • 14
    • 0012022093 scopus 로고
    • Although 6 is not drawn as an intermediate by the authors in ref 8, the conditions employed in step 1 of eq 2 are standard for deprotecting phenolic methoxymethyl ethers. Cf.:, In particular, note ref 4 of this paper
    • Although 6 is not drawn as an intermediate by the authors in ref 8, the conditions employed in step 1 of eq 2 are standard for deprotecting phenolic methoxymethyl ethers. Cf.: Yardely, J. P.; Fletcher, H., III. Synthesis 1976, 244. In particular, note ref 4 of this paper.
    • (1976) Synthesis , pp. 244
    • Yardely, J.P.1    Fletcher, H.2
  • 17
    • 0009580956 scopus 로고
    • For a discussion of the factors controlling the stereochemistry of azetidinones produced in the reaction of imines with acid chlorides/anhydrides see
    • For a discussion of the factors controlling the stereochemistry of azetidinones produced in the reaction of imines with acid chlorides/anhydrides see: (a) Moore, H. W.; Hernandez, L., Jr.; Chambers, R. J. Am. Chem. Soc. 1978, 100, 2245.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 2245
    • Moore, H.W.1    Hernandez, L.2    Chambers, R.3
  • 25
    • 85022264991 scopus 로고
    • When applied to compound 16 this protocol was vastly inferior to the one delineated in this paper
    • Chem. Abstr., 1971, 74, 12982. When applied to compound 16 this protocol was vastly inferior to the one delineated in this paper.
    • (1971) Chem. Abstr. , vol.74 , pp. 12982
  • 26
    • 0016720754 scopus 로고
    • For other methods of preparing N-unsubstituted azetidinones see, inter alia the following. (a) The review by:, and references therein
    • For other methods of preparing N-unsubstituted azetidinones see, inter alia the following. (a) The review by: Mukerjee, A. K.; Singh, A. K. Synthesis 1975, 547 and references therein,
    • (1975) Synthesis , pp. 547
    • Mukerjee, A.K.1    Singh, A.K.2


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