Patent ID: 6121455
Filing Date: 2000-09-19
Classification: C07D

Abstract:
A process for the preparation of a compound of the formula ##STR35## and, where applicable, its E/Z-isomers, mixtures of E/Z-isomers and/or tautomers, or a salt thereof, whereinQ is CH or N,Y is NO.sub.2 or CN,Z is CHR.sub.3, O, NR.sub.3 or S,R.sub.1 and R.sub.2 are either each independently of the other hydrogen or unsubstituted or R.sub.4 -substituted C.sub.1 -C.sub.8 alkyl, or together form an alkylene bridge having two or three carbon atoms, and said alkylene bridge may additionally contain a hetero atom selected from the group consisting of NR.sub.5, O and S,R.sub.3 is H or unsubstituted or R.sub.4 -substituted C.sub.1 -C.sub.12 alkyl,R.sub.4 is unsubstituted or substituted aryl or heteroaryl, andR.sub.5 is H or C.sub.1 -C.sub.12 alkyl;which comprisesa) reacting a compound of the formula ##STR36## and, where applicable, its E/Z-isomers, mixtures of E/Z-isomers and/or tautomers, or a salt thereof, whereinR is unsubstituted or substituted C.sub.1 -C.sub.12 alkyl, unsubstituted or substituted C.sub.2 -C.sub.4 alkenyl, unsubstituted or substituted C.sub.2 -C.sub.4 alkynyl, unsubstituted or substituted C.sub.3 -C.sub.6 cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocyclyl, or --SR.sub.6 ; andR.sub.6 is unsubstituted or substituted C.sub.1 -C.sub.12 alkyl, unsubstituted or substituted C.sub.2 -C.sub.4 alkenyl, unsubstituted or substituted C.sub.2 -C.sub.4 alkynyl, unsubstituted or substituted C.sub.3 -C.sub.6 cycloalkyl, unsubstituted or substituted aryl or unsubstituted or substituted heterocycyl,X.sub.1 is a leaving group;with a halogenating agent, in the presence of a base, to form a compound of the formula ##STR37## or, where applicable, an E/Z-isomer, a mixture of E/Z-isomers and/or a tautomer thereof, whereinR is as defined for formula (II);m is 0 or 1; andX is halogen; orb) converting a compound of formula (II) by means of a halogenating agent into a compound of the formula ##STR38## or, where applicable, an E/Z-isomer, a mixture of E/Z-isomers and/or a tautomer thereof, wherein R, X and X.sub.1 are as defined for formulae (II) and (III); optionallyc) converting a compound of formula (IV), in the absence or in the presence of a base, into a compound of formula (III);d) converting a compound of formula (III) by reacting with a compound of the formula ##STR39## or, where applicable, an E/Z-isomer, a mixture of E/Z-isomers and/or a tautomer thereof, or a salt thereof, wherein R.sub.1, R.sub.2, Y, Z and Q are as defined for the compound of formula (I), into a compound of the formula ##STR40## or, where applicable, an E/Z-isomer, a mixture of E/Z-isomers and/or a tautomer thereof, or a salt thereof, and wherein R.sub.1, R.sub.2, Y, Z and Q are as defined above for the compound of formula (I) and R is as defined above for the compound of formula (II); ore) converting a compound of formula (IV) by reaction with a compound of formula (V) into a compound of formula (VI); andf) converting a compound of formula (VI) by means of a chlorinating agent into a compound of formula (I).