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Volumn 13, Issue 3, 2011, Pages 486-489

1,3-dipolar cycloaddition-decarboxylation reactions of an azomethine ylide with isatoic anhydrides: Formation of novel benzodiazepinones

Author keywords

[No Author keywords available]

Indexed keywords

AZO COMPOUND; AZOMETHINE; BENZODIAZEPINE DERIVATIVE; ISATOIC ANHYDRIDE; OXAZINE DERIVATIVE; THIOSEMICARBAZONE DERIVATIVE;

EID: 79851471840     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102824k     Document Type: Article
Times cited : (72)

References (53)
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    • Padwa, A., Pearson, W. H., Eds.; Wiley: New York, NY, Chapter 3
    • (c) Harwood, L. M.; Vickers, R. J. Chemistry of Heterocyclic Compounds; Padwa, A., Pearson, W. H., Eds.; Wiley: New York, NY, 2003; Vol. 59, Chapter 3, p 169.
    • (2003) Chemistry of Heterocyclic Compounds , vol.59 , pp. 169
    • Harwood, L.M.1    Vickers, R.J.2
  • 36
    • 79851477931 scopus 로고    scopus 로고
    • Crystallographic data CIF for the structure reported in this manuscript have been deposited with the Cambridge Crystallographic Data Centre CCDC and allocated the deposition number CCDC-796928 for compound 5a. A copy of the data can be obtained free of charge on application to the CCDC, 12 Union Road, Cambridge, CB2 IEZ, UK; fax: 44 01223 336 033; email: deposit@ccdc.cam.ac.uk
    • Crystallographic data (CIF) for the structure reported in this manuscript have been deposited with the Cambridge Crystallographic Data Centre (CCDC) and allocated the deposition number CCDC-796928 for compound 5a. A copy of the data can be obtained free of charge on application to the CCDC, 12 Union Road, Cambridge, CB2 IEZ, UK; fax: (44) 01223 336 033; email: deposit@ccdc.cam.ac.uk.
  • 41
    • 79851482021 scopus 로고    scopus 로고
    • This result is in contrast to cycloaddition reactions of azomethine ylide 2a with benzaldehydes which appear to be unaffected by substitution with electron-donating groups see ref 6d
    • This result is in contrast to cycloaddition reactions of azomethine ylide 2a with benzaldehydes which appear to be unaffected by substitution with electron-donating groups (see ref 6d).
  • 42
    • 79851490102 scopus 로고    scopus 로고
    • 2Ph, 3.53 s, 2H, N4′, 3.38 s, 3H, N1Me
    • 2Ph), 3.53 (s, 2H, N4′), 3.38 (s, 3H, N1Me).
  • 43
    • 79851473497 scopus 로고    scopus 로고
    • instability of intermediate 7 has so far prevented its purification
    • The instability of intermediate 7 has so far prevented its purification.
  • 47
    • 70249141289 scopus 로고    scopus 로고
    • A related ring-opening and decarboxylation of spiro-benzooxazine pyrrolidines has recently been reported
    • A related ring-opening and decarboxylation of spiro-(benzooxazine) pyrrolidines has recently been reported: Nicolaou, K. C.; Krasovskiy, A.; Majunder, U.; Trepanier, V. E.; Chen, D. Y.-K. J. Am. Chem. Soc. 2009, 131, 3690.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 3690
    • Nicolaou, K.C.1    Krasovskiy, A.2    Majunder, U.3    Trepanier, V.E.4    Chen, D.Y.-K.5
  • 48
    • 79851478336 scopus 로고    scopus 로고
    • Alternative mechanisms, involving electrocyclic extrusion of carbon dioxide from 7 or 8, have been considered; however, these mechanisms would require formation of high energy nonaromatic intermediates
    • Alternative mechanisms, involving electrocyclic extrusion of carbon dioxide from 7 or 8, have been considered; however, these mechanisms would require formation of high energy nonaromatic intermediates.
  • 53
    • 67449108408 scopus 로고    scopus 로고
    • Gribble, G. W., Joule, J. A., Eds.; Elsevier Science Ltd.: Oxford, OX5 1GB, U. K., Chapter 7
    • (d) Smith, J. A.; Ryan, J. H. Prog. Het. Chem.; Gribble, G. W., Joule, J. A., Eds.; Elsevier Science Ltd.: Oxford, OX5 1GB, U. K., 2009; Vol. 20, Chapter 7, p 432.
    • (2009) Prog. Het. Chem. , vol.20 , pp. 432
    • Smith, J.A.1    Ryan, J.H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.