Patent TW-400325-B (TW)
Title: Process for the preparation of pyrrolidinone compound herbicides and their intermediates
Inventor: MATTHEWS IAN RICHARD
IPC: C07D207/273
Filed: 1996-05-16
Granted: 2000-08-01
Abstract: A process for the preparation of a compound of general formula II: wherein R1 is hydrogen or C1-C10 hydrocarbyl or heterocyclyl having 3 to 8 ring atoms, either of which may optionally be substituted with halogen (I.e. chlorine, bromine, fluorine or iodine), hydroxy, SO2NR<n>R<b> (where R<a> and R<b> are independently II or C1-C6 alkyl), SiR<c>3 (where each R<e> is independently C1-C4 alkyl or phenyl), cyano, nitro, amino, mono- and dialkylamino in which the alkyl groups have from 1 to 6 or more carbon atoms, acylamino, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulphinyl, C1-C6 alkylsulphonyl, carboxy, carboxyamide, in which the groups attached to the N atom may be hydrogen or optionally substituted lower hydrocarbyl; alkoxy carbonyl wherein the alkoxy group may have from 1 to 6 or more carbon atoms, or aryl such as phenyl; each R2, R3, R4 and R5 is independently hydrogen or C1-C4 alkyl; A is an aromatic or heteroaromatic ring system optionally substituted with one or more substituents selected from: halogen or C1-C10 hydrocarbyl, -O(C1-C10 hydrocarbyl), -S(C1-C10 hydrocarbyl), -SO(C1-C10 hydrocarbyl) or -SO2 (C1-C10 hydrocarbyl), cyano, nitro, SCN, SiR<e>3 (where each R<e> is independently C1-C4 alkyl or phenyl), COR7, CR7NOR8, NHOH, ONR7R8, SF5, COOR7, SO2NR7R8, OR9 or NR10R11; and in which any ring nitrogen atom may be quaternised or oxidised; alternatively, and any two substituents of the group A may combine to form a fused 5- or 6- membered saturated or partially saturated carbocyclic or heterocyclic ring in which any carbon or quaternised nitrogen atom may be substituted with any of the groups mentioned above for A or in which a ring carbon atom may be oxidised; R7 and R8 are each independently hydrogen or C1-C10 hydrocarbyl; R9 is hydrogen, C1-C10 hydrocarbyl, SO2(C1-C10 hydrocarbyl), CIIO, CO(C1-C10 hydrocarbyl), COO(C1-C10 hydrocarbyl) or CONR7R8; R10 and R11 are each independently hydrogen, C1-C10 hydrocarbyl, O(C1-C10 hydrocarbyl), SO2(C1-C10 hydrocarbyl), CHO, CO(C1-C10 hydrocarbyl), COO(C1-C10 hydrocarbyl) or CONR7R8; any of the hydrocarbyl groups within the group A may optionally be substituted with halogen (i.e. chlorine, bromine, fluorine or iodine), hydroxy, SO2NR<a>R<b> (where R<a> and R<b> are independently H or C1-C6 alkyl), cyano, nitro, amino, mono- and dialkylamino in which the alkyl groups have from 1 to 6 or more carbon atoms, acylamino, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulphinyl, C1-C6 alkylsulphonyl, carboxy, carboxyamide, in which the groups attached to the N atom may be hydrogen or lower hydrocarbyl optionally substituted with halogen; alkoxy carbonyl wherein the alkoxy group may have from 1 to 6 or more carbon atoms, or aryl such a sphenyl; R21 is hydrogen, halogen OH or OCONHR1, wherein R1 is as defined above; the process comprising cyclising a compound of general formula III: wherein A, R2, R3, R4, R5 and R21 are as defined in general formula II and R25 is leaving group such as a halogen atom; under basic conditions.