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Volumn 9, Issue 17, 2007, Pages 3283-3286

Enantiopure 1,4-benzoxazines via 1,2-cyclic sulfamidates. Synthesis of levofloxacin

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; BENZOXAZINE DERIVATIVE; OFLOXACIN; SULFONAMIDE;

EID: 34548179023     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0712475     Document Type: Article
Times cited : (96)

References (32)
  • 1
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    • For a review on the synthesis and reactivity of cyclic sulfamidates, see: Meléndez, R. E.; Lubell, W. D. Tetrahedron 2003, 59, 2581-2616. Six-ring cyclic sulfamidates, where nitrogen is part of an aziridine ring system, undergo nucleophilic cleavage preferentially at the C-N bond to afford substituted seven-ring cyclic sulfamidates:
    • For a review on the synthesis and reactivity of cyclic sulfamidates, see: Meléndez, R. E.; Lubell, W. D. Tetrahedron 2003, 59, 2581-2616. Six-ring cyclic sulfamidates, where nitrogen is part of an aziridine ring system, undergo nucleophilic cleavage preferentially at the C-N bond to afford substituted seven-ring cyclic sulfamidates:
  • 10
    • 21744433017 scopus 로고    scopus 로고
    • For a recent review covering the synthesis and biological importance of 1,4-benzoxazines, see
    • For a recent review covering the synthesis and biological importance of 1,4-benzoxazines, see: Ilaš, J.; Anderluh, P. Š.; Dolenc, M. S.; Kikelj, D. Tetrahedron 2005, 61, 7325-7348.
    • (2005) Tetrahedron , vol.61 , pp. 7325-7348
    • Ilaš, J.1    Anderluh, P.S.2    Dolenc, M.S.3    Kikelj, D.4
  • 11
    • 33751218041 scopus 로고    scopus 로고
    • For recent approaches to 1,4-benzoxazines and related heterocyclic scaffolds, see: a
    • For recent approaches to 1,4-benzoxazines and related heterocyclic scaffolds, see: (a) Wolfer, J.; Bekele, T.; Abraham, C J.; Dogo-Isonagie, C.; Lectka, T. Angew. Chem., Int. Ed. 2006, 45, 7398-7400.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 7398-7400
    • Wolfer, J.1    Bekele, T.2    Abraham, C.J.3    Dogo-Isonagie, C.4    Lectka, T.5
  • 15
    • 0028356205 scopus 로고    scopus 로고
    • Openings of 1,2-cyclic sulfamidates with 2-methoxyphenolate have previously been reported in 47-82% isolated yield: Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586.
    • Openings of 1,2-cyclic sulfamidates with 2-methoxyphenolate have previously been reported in 47-82% isolated yield: Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586.
  • 16
    • 0008165462 scopus 로고    scopus 로고
    • For a review on Pd-catalyzed amination. see: (a) Yang, B. H.; Buchwald. S. L. J. Organomet. Chem. 1999, 576, 125-146. For a previous approach to benzoxazines using Ni(0)-mediated intramolecular amination of aryl chlorides, see:
    • For a review on Pd-catalyzed amination. see: (a) Yang, B. H.; Buchwald. S. L. J. Organomet. Chem. 1999, 576, 125-146. For a previous approach to benzoxazines using Ni(0)-mediated intramolecular amination of aryl chlorides, see:
  • 17
    • 0141853186 scopus 로고    scopus 로고
    • For an example using Pd(0)-mediated intramolecular amination of an aryl chloride, see
    • (b) Omar-Amrani, R.: Thomas, A.; Brenner, E.; Schneider, R.; Fort, Y. Org. Lett. 2003, 5, 2311-2314. For an example using Pd(0)-mediated intramolecular amination of an aryl chloride, see:
    • (2003) Org. Lett , vol.5 , pp. 2311-2314
    • Omar-Amrani, R.1    Thomas, A.2    Brenner, E.3    Schneider, R.4    Fort, Y.5
  • 19
    • 15744365005 scopus 로고    scopus 로고
    • For a previous synthesis of a quinoxalinone via intramolecular Pd-(0)-mediated amination of an aryl iodide, see: Kitagawa. O.; Takahashi,M.; Yoshikawa, M.; Taguchi. T. J. Am. Chem. Soc. 2005, 127, 3676-3677.
    • For a previous synthesis of a quinoxalinone via intramolecular Pd-(0)-mediated amination of an aryl iodide, see: Kitagawa. O.; Takahashi,M.; Yoshikawa, M.; Taguchi. T. J. Am. Chem. Soc. 2005, 127, 3676-3677.
  • 20
    • 0142227985 scopus 로고    scopus 로고
    • Other ligands screened included BINAP which gave 9a in 76% yield and Verkade's TTPU ligand (Urgaonkar, S.; Xu, J. H.; Verkade, J. G. J. Org. Chem. 2003, 68, 8416-8423) which gave 9a in 86% yield.
    • Other ligands screened included BINAP which gave 9a in 76% yield and Verkade's TTPU ligand (Urgaonkar, S.; Xu, J. H.; Verkade, J. G. J. Org. Chem. 2003, 68, 8416-8423) which gave 9a in 86% yield.
  • 21
    • 34548164316 scopus 로고    scopus 로고
    • An example of a successful Pd-catalyzed cyclization to form a related seven-ring system has been reported
    • An example of a successful Pd-catalyzed cyclization to form a related seven-ring system has been reported.
  • 22
    • 0042330510 scopus 로고    scopus 로고
    • For the preparation of 10d, see
    • For the preparation of 10d, see: Novak, Z.; Timar, G.; Kotschy, A. Tetrahedron 2003, 59, 7509-7513.
    • (2003) Tetrahedron , vol.59 , pp. 7509-7513
    • Novak, Z.1    Timar, G.2    Kotschy, A.3
  • 31
    • 0037178344 scopus 로고    scopus 로고
    • Tewson has previously reported the synthesis of cyclic sulfamidate 15 in 78% yield from 14: Posakony, J. J.; Grierson, J. R.; Tewson, T. J. J. Org. Chem. 2002, 67, 5164-5169.
    • Tewson has previously reported the synthesis of cyclic sulfamidate 15 in 78% yield from 14: Posakony, J. J.; Grierson, J. R.; Tewson, T. J. J. Org. Chem. 2002, 67, 5164-5169.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.