Patent ID: 6437145
Filing Date: 2002-08-20
Classification: C07C,C07D

Abstract:
A method of producing oxazolidinones of formula in whichR1 signifies hydrogen; (C1-C12)-alkyl; (C2-C10)-alkenyl; (C2-C10)-alkinyl; (C1-C6)-alkyl which is substituted singly or multiply by the same or different groups selected from the group consisting of halogen, (C1-C4)-alkoxy, (C1-C4)-alkylthio, â€”CN, (C2-C5)-alkoxycarbonyl and (C2-C6)-alkenyl; (C3-C8)-cycloalkyl which is unsubstituted or substituted by one or more groups selected from the group consisting of (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylthio and halogen; (C5-C8)-cycloalkenyl; aryl or aryl-(C1-C4)-alkyl which are unsubstituted or substituted in the aryl group; â€”OR6; NR7R8; or stands in conjunction with the adjacent carbonyl group for a protective group selected from the group consisting of boc, Z, TFA, alloc, teoc, formyl, fmoc and moc, for protecting the amino group of an amino acid; R2 and R3 may be the same or different and signify, independently of one another, hydrogen, (C1â€˜C8)-alkyl or (C3-C8)-alkenyl, (C3-C8)-alkinyl or (C3-C8)-cycloalkyl, which above C-containing groups are unsubstituted or substituted singly or multiply, up to three times, by the same or different groups selected from the group consisting of halogen, hydroxy, (C1-C8)-alkoxy, (C1-C8)-alkylmercapto, (C2-C8)-alkenylmercapto, (C2-C8)-alkinylmercapto, (C2-C8)-alkenyloxy, (C2-C8)-alkinyloxy, (C3-C7)-cycloalkyl, (C3-C7)-cycloalkoxy, cyano, mono- and di-(C1-C4alkyl)-amino, aryl and aryl-(C1-C6)-alkoxy, in which the aryl groups can be unsubstituted or substituted singly or multiply, up to three times, by the same or different groups selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-halogen alkyl and (C1-C4)-halogen alkoxy; and which groups R2 and R3 can be connected together to form a 3-10-member ring which can contain an N, O, or S-heterosubstitution in addition to the cited substituents; R4 signifies hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkinyl, aryl, alkaryl, aralkyl, or cycloalkyl; R5 signifies a (C1-C2)-alkane diyl chain which can be substituted with up to four groups selected from the group consisting of (C1-C4)-alkyl groups, (C3-C4)-alkenyl groups, (C3-C4)-alkinyl groups, (C3-C8)-cycloalkyl groups and aryl groups, which alkane diyl chain and its substituents can be N, O, S-heterosubstituted in lieu of a carbon atom; and two of the substituents of the alkane diyl chain can be connected to one another or to one of the substituents of the alkane diyl chain with an R4 group optionally to form a ring structure; R6 signifies hydrogen, (C1-C18)-alkyl, (C3-C12)-cycloalkyl, (C2-C8)-alkenyl or (C2-C8)-alkinyl, which above C-containing groups are unsubstituted or may be substituted singly or multiply, up to three times, by one or more moieties selected from the group consisting of: halogen, hydroxy, (C1-C8)-alkoxy, (C1-C8)-alkylmercapto, (C2-C8)-alkenylmercapto, (C2-C8)-alkinylmercapto, (C2-C8)-alkenyloxy, (C2-C8)-alkinyloxy, (C3-C7)-cycloalkyl, (C3-C7)-cycloalkoxy, cyano, mono- and di-(C1-C4-alkyl)-amino, carboxy, (C1-C8)-alkoxycarbonyl, (C2-C8)-alkenyloxycarbonyl, (C1-C8)-alkylmercaptocarbonyl, (C2-C8)-alkinyloxycarbonyl, (C1-C8)-alkylcarbonyl, (C2-C8) alkenylcarbonyl, (C2-C8)-alkinylcarbonyl, 1-(hydroxy imino)-(C1-C6)-alkyl, 1-{(C1-C4)-alkylimino}-(C1-C4)-alkyl, 1-{(C1-C4)-alkoxyimino}(C1-C6)-alkyl, (C1-C8)-alkylcarbonyl amino, (C2-C8)-alkenylcarbonyl amino, (C2-C8)-alkinylcarbonyl amino, amino carbonyl, (C1-C8)-alkylamino carbonyl, di-(C1-C6)-alkylamino carbonyl, (C2-C6)-alkenylamino carbonyl, (C2-C6)-alkinylamino carbonyl, (C1-C8)-alkoxycarbonyl amino, (C1-C8)-alkylamino carbonyl amino, (C1-C6)-alkylcarbonyloxy, which is unsubstituted or substituted by halogen, nitro, (C1-C4)-alkoxy or optionally substituted phenyl, (C2-C6)-alkenylcarbonyloxy, (C2-C6)-alkinylcarbonyloxy, (C1-C8)-alkylsulfonyl, phenyl, phenyl-(C1-C6)-alkoxy, phenyl-(C1-C6)-alkoxycarbonyl, phenoxy, phenoxy-(C1-C6)-alkoxy, phenoxy-(C1-C6)-alkoxycarbonyl, phenylcarbonyloxy, phenylcarbonyl amino, phenyl-(C1-C6)-alkylcarbonyl amino;in which the phenyl rings of said moieties are independently unsubstituted or substituted singly or multiply, up to three times, by groups that are the same or different and are selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-halogen alkyl, (C1-C4)-halogen alkoxy and nitro, and groups of formulas â€”SiRâ€²3, â€”Oâ€”SiRâ€²3, Râ€²3Siâ€”(C1-C8)-alkoxy, â€”COâ€”Oâ€”NRâ€²2, â€”Oâ€”N&boxH;CRâ€²2, â€”N&boxH;CRâ€²2, â€”Oâ€”NRâ€²2, CH(ORâ€²)2 and â€”Oâ€”(CH2)mâ€”CH(ORâ€²)2 each Râ€² signifies, independently of each other Râ€², hydrogen, (C1-C4)-alkyl, phenyl, which is unsubstituted or substituted singly or multiply, up to three times, by groups that are the same or different selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-halogen alkyl, (C1-C4)-halogen alkoxy and nitro, or signify in pairs a (C2-C6)-alkane diyl chain, and m=0 to 6; andR7 and R8 are the same or different and signify independently of one, the same groups as are indicated for R6 and R7 and R8 also are optionally connected among themselves to form a ring; by reacting cyclic anhydrides of formula II in which R1, R4 and R5 have the significance indicated for formula I, with carbonyl compounds of formula III in which R2 and R3 have the significance indicated for formula I, or with compounds which produce, as precursors of the compounds of formula III under the conditions of the reaction, compounds of formula III during the reaction at temperatures between room temperature and approximately 150Â° C.