| 摘要 |
The present invention discloses a process to produce a compound of the formula (IA): <IMAGE> (IA) or an acid addition salt or metal complex thereof, in which n represents an integer from 0 to 5; each R represents a halogen atom, or a nitro, cyano, alkyl, haloalkyl or phenyl group; R1 and R2 independently represent a hydrogen atom or an alkyl group; and A represents a nitrogen atom or a CH group; which comprises steps of: (1-a) reacting a compound of the formula (VI): <IMAGE> (VI) in which n,R,R1 and R2 are as defined above, with a reducing agent to obtain a compound of the formula (IVA); or, as an alternative step, (1-b) reacting a compound of the formula (VII): <IMAGE> (VII) in which n, R,R1 and R2 are as defined above and R5 represents a hydrogen atom or an alkyl group, with a reducing agent to obtain a compound of the formula (IVA); (2) reacting a compound of the formula (IVA): <IMAGE> (IVA) with a compound of the formula (V): R3SO2X(V) in which n,R,R1 and R2 are as defined above and R3 represents a C1-4 alkyl group or a phenyl group each optionally substituted by one or more substituents selected from halogen atoms, nitro, cyano, hydroxyl, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkyl, amino, C1-4 alkylamino, di-C1-4 alkylamino, C1-4 alkoxycarbonyl, carboxyl, C1-4 alkanoyl, C1-4 alkylthio, C1-4 alkylsulphinyl, C1-4 alkylsulphonyl, carbamoyl, C1-4 alkylamido, C3-8 cycloalkyl and phenyl groups and X represents a halogen atom, in the presence of a base to obtain a compound of the formula (IIA); (3) reacting a compound of the formula (IIA): <IMAGE> (IIA) with a compound of the formula (III): <IMAGE> (III) in which n,R,R1, R2, R3 and A are as defined above and Q represents a hydrogen or alkali metal atom, in the presence of a base to obtain a compound of the formula (IA), and optionally converting the resulting compound of the formula (IA) into an acid addition salt or metal complex thereof.
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