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Volumn 72, Issue 13, 2007, Pages 4832-4836

Easy access to new heterocyclic systems: 1,4-Oxazine and substituted 1,4-oxazines

Author keywords

[No Author keywords available]

Indexed keywords

CROSS-COUPLING REACTIONS; HETEROCYCLIC DERIVATIVES; OXAZINE;

EID: 34250821664     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070528n     Document Type: Article
Times cited : (50)

References (48)
  • 1
    • 33644839988 scopus 로고    scopus 로고
    • For diversity-oriented synthesis, see
    • (a) For diversity-oriented synthesis, see: Tan, D. S. Nat. Chem. Biol. 2005, 1, 74.
    • (2005) Nat. Chem. Biol , vol.1 , pp. 74
    • Tan, D.S.1
  • 8
    • 9644303130 scopus 로고    scopus 로고
    • For a recent review on biologically active 1,4-benzoxazine derivatives, see the following: a, and references therein
    • For a recent review on biologically active 1,4-benzoxazine derivatives, see the following: (a) Achari, B.; Mandal, S. B.; Dutta, P. K.; Chowdhury, C. Synlett 2004, 2449 and references therein.
    • (2004) Synlett , pp. 2449
    • Achari, B.1    Mandal, S.B.2    Dutta, P.K.3    Chowdhury, C.4
  • 17
    • 0020378652 scopus 로고    scopus 로고
    • The sole literature precedent: Herbert, B. Arch. Pharm. 1982, 315, 684.
    • The sole literature precedent: Herbert, B. Arch. Pharm. 1982, 315, 684.
  • 25
    • 0034727939 scopus 로고    scopus 로고
    • (f) Coe, J. W. Org. Lett. 2000, 2, 4205.
    • (2000) Org. Lett , vol.2 , pp. 4205
    • Coe, J.W.1
  • 34
    • 24144432795 scopus 로고    scopus 로고
    • Other research in this field:, and references cited therein
    • (o) Other research in this field: Occhiato, E.G.; Lo Galbo, F.; Guarna, A. J. Org. Chem. 2005, 70, 7324 and references cited therein.
    • (2005) J. Org. Chem , vol.70 , pp. 7324
    • Occhiato, E.G.1    Lo Galbo, F.2    Guarna, A.3
  • 37
    • 34250834455 scopus 로고    scopus 로고
    • The bisvinylphosphate 3 is stable for several months at 4°C under argon atmosphere.
    • The bisvinylphosphate 3 is stable for several months at 4°C under argon atmosphere.
  • 42
    • 34250828540 scopus 로고    scopus 로고
    • Addition of HMPA, which stabilizes the formed anion, was in most cases useful to improve the reaction's yield.
    • Addition of HMPA, which stabilizes the formed anion, was in most cases useful to improve the reaction's yield.
  • 46
    • 0003417469 scopus 로고
    • Trost, B. M, Ed, Pergamon: New York, Chapter 2.4
    • (d) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 3, Chapter 2.4.
    • (1991) Comprehensive Organic Synthesis , vol.3
    • Sonogashira, K.1
  • 47
    • 34250878476 scopus 로고    scopus 로고
    • In the case of compounds 6c and 6k, only 1.5 equiv of n-BuLi (instead of 2 equiv) was used in order to preclude the reaction of the base directly on the 3,4,5-trimethoxyaldehyde. The obtained corresponding alcohol is difficult to separate effectively from the desired trisubstituted compound
    • In the case of compounds 6c and 6k, only 1.5 equiv of n-BuLi (instead of 2 equiv) was used in order to preclude the reaction of the base directly on the 3,4,5-trimethoxyaldehyde. The obtained corresponding alcohol is difficult to separate effectively from the desired trisubstituted compound.
  • 48
    • 34250838097 scopus 로고    scopus 로고
    • The regioselective functionalization of the oxazine 5 at the C-3 position was confirmed by the following reaction. The analytical data of compound 11 are depicted in the Experimental Section. (Chemical Equation Presented)
    • The regioselective functionalization of the oxazine 5 at the C-3 position was confirmed by the following reaction. The analytical data of compound 11 are depicted in the Experimental Section. (Chemical Equation Presented)


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