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Volumn , Issue 14, 2005, Pages 2426-2432

Synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones by thermally induced cyclization of N-(2-benzyloxycarbonyl)phenyl ketenimines; oxygen-to-carbon migration of a benzyl group

Author keywords

Azides; Benzoxazinones; Cyclizations; Ketenimines; Rearrangements

Indexed keywords

CHEMICAL BONDS; ESTERS; FUNCTIONS;

EID: 24944532580     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-870015     Document Type: Article
Times cited : (18)

References (69)
  • 15
    • 0032778402 scopus 로고    scopus 로고
    • (a) For a review on the synthesis and reactivity of 4H-3,1-benzoxazin-4- ones bearing a carbon substituent at the 2 position see: Coppola, G. M. J. Heterocycl. Chem. 1999, 36, 563.
    • (1999) J. Heterocycl. Chem. , vol.36 , pp. 563
    • Coppola, G.M.1
  • 16
    • 0034491821 scopus 로고    scopus 로고
    • (b) For a review on the synthesis and reactivity of 4H-3,1-benzoxazin-4- ones bearing oxy, mercapto or amino functionalities at the 2-position see: Coppola, G. M. J. Heterocycl. Chem. 2000, 37, 1369.
    • (2000) J. Heterocycl. Chem. , vol.37 , pp. 1369
    • Coppola, G.M.1
  • 17
    • 37049124033 scopus 로고
    • For examples of preparations of 2-substituted 4H-3,1-benzoxazin-4-ones from anthranilic acids, see: (a) Bain, D. I.; Smalley, R. K. J. Chem. Soc. C 1968, 1593.
    • (1968) J. Chem. Soc. C , pp. 1593
    • Bain, D.I.1    Smalley, R.K.2
  • 23
    • 0000090606 scopus 로고
    • For examples of preparations of 2-substituted 4H-3,1-benzoxazin-4-ones from N-acylanthranilic acids see: (a) Zentmyer, D. T.; Wagner, E. C. J. Org. Chem. 1948, 13, 967.
    • (1948) J. Org. Chem. , vol.13 , pp. 967
    • Zentmyer, D.T.1    Wagner, E.C.2
  • 55
    • 24944531594 scopus 로고    scopus 로고
    • note
    • Ketenimines 5 and 7 remained unaltered when heated in boiling toluene or boiling ortho-xylene.
  • 56
    • 24944562232 scopus 로고    scopus 로고
    • note
    • 3], respectively.
  • 57
    • 24944561372 scopus 로고    scopus 로고
    • CCDC 264507 contains the supplementary crystallographic data for 6g. The data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; email:deposit@ccdc. cam.ac.uk).
  • 67
    • 0030837671 scopus 로고    scopus 로고
    • 2-Azidobenzoyl chloride (1a) and 2-azido-5-chlorobenzoyl chloride (1b) were both prepared following the experimental procedure described for 1a: Porter, T. C.; Smalley, R. K.; Teguiche, M.; Purwono, B. Synthesis 1997, 773.
    • (1997) Synthesis , pp. 773
    • Porter, T.C.1    Smalley, R.K.2    Teguiche, M.3    Purwono, B.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.