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Volumn 49, Issue 5, 2008, Pages 835-839

Microwave assisted ring-opening of epoxides with N-biaryl sulfonamides in the synthesis of matrix metalloproteinase-9 inhibitors

Author keywords

Epoxide; Matrix metalloproteinase; Microwave; MMP; Ring opening; Sulfonamide

Indexed keywords

ALKANESULFONAMIDE DERIVATIVE; EPOXIDE; GELATINASE B; GELATINASE INHIBITOR; SULFONAMIDE; UNCLASSIFIED DRUG;

EID: 37649025655     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.184     Document Type: Article
Times cited : (13)

References (17)
  • 1
    • 0000496226 scopus 로고    scopus 로고
    • For representative examples, see:. Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds), Springer-Verlag, Berlin, Germany
    • For representative examples, see:. Jacobsen E.N., and Wu M.H. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis I-III Vol. 3 (1999), Springer-Verlag, Berlin, Germany 1306-1326
    • (1999) Comprehensive Asymmetric Catalysis I-III , vol.3 , pp. 1306-1326
    • Jacobsen, E.N.1    Wu, M.H.2
  • 7
    • 1842763607 scopus 로고    scopus 로고
    • An example on intramolecular cyclization using trifluoroacetic acid, see:
    • An example on intramolecular cyclization using trifluoroacetic acid, see:. Goujon J.-Y., Zammattio F., Chrětien J.M., and Beaudet I. Tetrahedron 60 (2004) 4037-4049
    • (2004) Tetrahedron , vol.60 , pp. 4037-4049
    • Goujon, J.-Y.1    Zammattio, F.2    Chrětien, J.M.3    Beaudet, I.4
  • 12
    • 37649002057 scopus 로고    scopus 로고
    • note
    • 6S: C, 56.98; H, 5.58; N, 3.69. Found: C, 56.88; H, 5.54; N, 3.61.
  • 13
    • 28244465504 scopus 로고    scopus 로고
    • 1H NMR analysis of the crude mixture. The ring opening of styrene oxide usually associates with the regioselectivity issue. Some examples see: and Refs. 3a and 5d
    • 1H NMR analysis of the crude mixture. The ring opening of styrene oxide usually associates with the regioselectivity issue. Some examples see:. Placzek A.T., Donelson J.L., Trivedi R., Gibbs R.A., and De S.K. Tetrahedron Lett. 46 (2005) 9029-9034 and Refs. 3a and 5d
    • (2005) Tetrahedron Lett. , vol.46 , pp. 9029-9034
    • Placzek, A.T.1    Donelson, J.L.2    Trivedi, R.3    Gibbs, R.A.4    De, S.K.5
  • 14
    • 37649006759 scopus 로고    scopus 로고
    • note
    • Under the same irradiation using DMF as the solvent, 55% isolated yield of 13 was obtained. Under a thermal condition (90 °C, 24 h) or a microwave condition (DMF, 120 °C, 40 min), low conversion (<15%) was observed. In addition, the microwave condition (DMSO, 180 °C, 90 min) was also able to promote the ring opening of 5f with N-(4-methylphenyl)methyl 2-propanesulfonamide 19 to afford rac-20 (60%){A figure is presented}.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.