Substituted hydroquinone derivatives

C - Chemistry – Metallurgy – 07 – C

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C07C 43/23 (2006.01) C07C 69/92 (2006.01) C07D 211/62 (2006.01) C07D 405/04 (2006.01) C07F 7/08 (2006.01) C07F 9/40 (2006.01) C07F 9/54 (2006.01) C07F 9/59 (2006.01)

Patent

CA 2080683

4-18816/A Substituted hydroquinone derivatives Abstract Compounds of formula I Image (I), wherein R4 is lower alkyl and either R1 is hydroxy,halogen, a group of the formula -P(=O)(R5)R6 (Ia),a group of the formula -P+(R7)(R8)R9X-(Ib) or a group of the formula -Si(R7)(R8)R9(Ic),M is methylene,R2 is hydrogen or a group of the formula (Id) Image and R3 is hydrogen or halogen, or R1 is hydroxy or lower alkoxy, M is carbonyl, R2 is hydrogen and R3 is halogen, each of R5 and R6, independently of the other, is lower alkyl, lower alkoxy or N,N-di-lower alkylamino, or is benzyl, benzyloxy, phenyl or phenoxy, each of which is unsubstituted or mono- or di-substituted at the phenyl ring, wherein the substituents of the phenyl ring may be selected in each case from the group consisting of lower alkyl, lower alkoxy, nitro and halogen, each of R7, R8 and R9 independently of the others, is lower alkyl, unsubstituted or mono- or di-substituted phenyl, wherein the substituents of the phenyl ring may be selected in each case from the group consisting of lower alkyl, lower alkoxy, nitro and halogen, or is furyl, X- is the anion of a hydrohalic acid, a lower alkanesulfonic acid, a halo-lower alkanesulfonic acid or of a benzenesulfonic acid that is unsubstituted or mono-substituted by lower alkyl or by halogen, and wherein either Y is a direct bond and R10 is lower alkyl, allyl, cyano, lower alkanesulfonyl, halo- lower alkanesulfonyl, benzyl that is unsubstituted or mono- or di-substituted at the phenyl ring, wherein the substituents of the phenyl ring may be selected from the group consisting of lower alkyl, lower alkoxy, nitro and halogen, or is benzenesulfonyl that is unsubstituted or mono-substituted by lower alkyl or by halogen, or Y is a group of the formula-(C=O)- (Ie) or a group of the formula -(C=S)- (If) and R10 is halogen, lower alkyl, halo- lower alkyl, lower alkoxy, lower alkenyloxy, phenyl-lower alkenyloxy, halo-lower alkoxy or lower alkylthio, or is phenyl, phenoxy, phenylthio, benzyl, benzyloxy or benzylthio, each of which is unsubstituted or mono- or di-substituted at the phenyl ring, wherein the substituents of the phenyl ring may be selected in each case from the group consisting of lower alkyl, lower alkoxy, nitro and halogen, with the proviso that, in a compound I wherein R1 is a group Ib wherein each of R7, R8 and R9 is unsubstituted phenyl and X- is the bromide ion, M is methylene, R2 is hydrogen and R4 is methyl, R3 is other than hydrogen, and with the further proviso that, in a compound I wherein Rl is hydroxy, M is methylene, R2 is hydrogen and R4 is methyl or ethyl, R3 is other than hydrogen, can be used for the preparation of compounds of the formula Image (XII), wherein R3 is halogen, R4 is lower alkyl and R10 and Y are as defined, and salts thereof. They are prepared in accordance with methods known per se.

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