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METHOD FOR THE PRODUCTION OF OXAZOLES BY CONDENSING AROMATIC ALDEHYDES WITH a-KETOXIMES TO N-OXIDES AND THEN REACTING THE SAME WITH ACTIVATED ACID DERIVATIVES

  • US 20090286988A1
  • Filed: 07/27/2009
  • Published: 11/19/2009
  • Est. Priority Date: 12/15/2004
  • Status: Active Grant
First Claim
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1. A compound of formula III, wherein:

  • R1, R2 and R3 are each independently H, (C1-C6)-alkyl, F, Cl, Br, I, O—

    (C0-C8)-alkylene-H, CF3, OCF3, SCF3, SF5, OCF2

    CHF2, (C6-C10)-aryl, O—

    (C6-C10)-aryl, O—

    (C1-C4)-alkylene-(C6-C10)-aryl, NO2, COOR9, CONR10R11, SH, or NR10R11, wherein the aryl is unsubstituted or mono-, di- or trisubstituted by F, Cl, Br, I, (C1-C4)-alkyl, O—

    (C1-C4)-alkyl or CF3;

    R9 is H, (C1-C8)-alkyl, Li, Na, K, ½

    Mg, ½

    Ca, or an ammonium ion which is un-substituted or mono-, di- or trisubstituted by (C1-C4)-alkyl;

    R10 and R11 are each independently H, (C1-C5)-alkyl, phenyl or CH2-phenyl, wherein the phenyl is un-substituted or mono-, di- or tri-substituted by F, Cl, Br, I, (C1-C4)-alkyl, O—

    (C1-C4)-alkyl or CF3, orR10 and R11 together are (C4-C5)-alkylene, wherein one CH2 group may be replaced by O, S, NH, N—

    CH3 or N-benzyl;

    W is CH, or N when o is 1;

    W is O, S, or NR12 when o is 0;

    o is 0 or 1;

    R12 is H, (C1-C6)-alkyl, (C1-C6)-alkylenephenyl, or phenyl;

    R4 is H, COOR9, CONR(10)R(11), (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C1-C3)-alkylene-(C3-C8)-cycloalkyl, phenyl, (C1-C3)-alkylenephenyl, (C5-C6)-heteroaryl, (C1-C3)-alkylene-(C5-C6)-heteroaryl, or (C1-C3)-alkyl, wherein the (C1-C3)-alkyl is fully or partly substituted by F;

    R5 and R6 are each independently H, (C1-C8)-alkyl, F, Cl, Br, I, O—

    (C0-C8)-alkylene-H, O—

    (C6-C10)-aryl, O—

    (C1-C4)-alkylene-(C6-C10)-aryl, COOR9, CONR10R11, SH or NR10R11, orR5 and R6 together are (C4-C5)-alkylene, wherein one CH2 group may be replaced by O, S, NH, N—

    CH3 or N-benzyl;

    R7 is H;

    n1 is 0, 1, ½

    or ⅓

    ; and

    HX1 is HCl, HBr, H2SO4, H3PO4, HOOCCF3, HOOCCCl3, HO3SCF3, HO3SCH3, HO3SC6H5, HO3S—

    C6H4-p-CH3, or HOOCH.

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