Chemical process

A process for the preparation of a compound of general formula (IV):

• ##STR7## wherein Z.sup.1 is a halogen atom;
• the process comprising reacting a compound of formula (X):
• ##STR8## with a compound of general formula (III):
• ##STR9## wherein Z.sup.1 is as defined above and Z.sup.2 is a halogen atom, in the presence of a methoxide anion.

A process for the preparation of a general formula (IV):

• ##STR10## wherein Z.sup.1 is a halogen atom;
• the process, which is carried out in the presence of methanol, comprising the steps of:
• (a) reacting a compound of formula (X):
• ##STR11## with a compound of formula ROCH.sub.3, wherein R is a metal;
• and, (b) reacting the product of (a) with a compound of general formula (III):
• ##STR12## wherein Z.sup.1 is as defined above, and Z.sup.2 is a halogen atom.

A process for the preparation of a compound of general formula (V):

• ##STR13## wherein Z.sup.1 is a halogen atom;
• the process comprising the steps of:
• a) reacting a compound of formula (X):
• ##STR14## with a compound of formula ROCH wherein R is a metal;
• and b) reacting the product formed in (a) with a compound of general formula (III):
• ##STR15## wherein Z.sup.1 is as defined above and Z.sup.2 is a halogen atom.

A process for the preparation of a compound of formula (I):

• ##STR16## wherein W is (CH.sub.3 O).sub.2 CH.CHCO.sub.2 CH.sub.3 or CH.sub.3 O.CH.dbd.CCO.sub.2 CH.sub.3 ;
• Z.sup.1 is a halogen atom;
• and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, acetoxy or acyl;
• the process comprising the steps of:
• (a) reacting a compound of formula (II):
• ##STR17## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined above, with a compound of formula ROCH.sub.3, wherein R is a metal;
• and,
• (b) reacting the product of (a) with a compound of formula (III):
• ##STR18## wherein Z.sup.1 and Z.sup.2 are halogen atoms;
• step (b) being carried out in the presence of methanol.

A process for the preparation of a compound of formula (VI):

• ##STR19## and stereoisomers thereof, wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, acetoxy or acyl;
• and Y and Z are, independently, hydrogen, halogen, cyano, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy, CSNH.sub.2, CONH.sub.2 or nitro;
• the process comprising the steps of:
• a) reacting a compound of formula (II):
• ##STR20## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined above;
• with a compound of formula ROCH.sub.3 wherein R is a metal;
• b) reacting the product of (a) with a compound of formula (III):
• ##STR21## wherein Z.sup.1 and Z.sup.2 are halogen atoms;
• and 1) (c) eliminating methanol from the compound of formula (I);
• ##STR22## wherein Z.sup.1 is a halogen atom:
• R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined above, and W is (CH.sub.3 O).sub.2 CHCHCO.sub.2 CH.sub.3, in the mixture of products from (b);
• and
• (d) reacting the product of (c) with a compound of formula (VII):
• ##STR23## wherein Z and Y are as defined above;
• or 2) (c) reacting the product of (b) with a compound of formula (VII):
• ##STR24## wherein Z and Y are as defined above;
• and (d) (i) separating the compound of formula (VI);
• or
• (ii) eliminating methanol from the compound of formula (VIII):
• ##STR25## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, Y and Z are as defined above, in the mixture of products from (c);
• or
• (iii) separating a compound of formula (VIII) from the mixture of products from (c) and eliminating methanol from it;
• or
• 3) (c) separating the compounds of formula (I), wherein W is (CH.sub.3 O).sub.2 CHCHCO.sub.2 CH.sub.3 and CH.sub.3 O.CH.dbd.CCO.sub.2 CH.sub.3, in the mixture of products from (b);
• and
• (d) (i) reacting the compound of formula (I), wherein W is CH.sub.3 O.CH.dbd.CCO.sub.2 CH.sub.3, with a compound of formula (VII);
• ##STR26## wherein Y and Z are defined above;
• or (ii) reacting the compound of formula (I), wherein W is (CH.sub.3 O).sub.2 CHCHCO.sub.2 CH.sub.3, with a compound of formula (VII):
• ##STR27## and eliminating methanol from the product so formed;
• or (iii) eliminating methanol from the compound of formula (I), wherein W is (CH.sub.3 O).sub.2 CHCHCO.sub.2 CH.sub.3, and reacting the product so formed with a compound of formula (VII):
• ##STR28## wherein Y and Z are as defined above.

A process for the preparation of a compound of formula (I):

• ##STR29## wherein W is (CH.sub.3 O).sub.2 CH.CHCO.sub.2 CH.sub.3 or CH.sub.3 O.CH.dbd.CCO.sub.2 CH.sub.3 ;
• Z.sup.1 is a halogen atom;
• and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -.sub.4 alkoxy, acetoxy or acyl;
• the process comprising the steps of:
• i) (a) reacting a compound of formula (XWV):
• ##STR30## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined above, with trimethyl orthoformate;
• (b) reacting the product of step (a) with a compound of formula ROCH.sub.3, wherein R is a metal;
• and,
• (c) reacting the product of step (b) with a compound of formula (III):
• ##STR31## wherein Z.sup.1 and Z.sup.2 are halogen atoms;
• or ii) (a) reacting a compound of formula (XIV):
• ##STR32## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined above, with a dimethoxymethyl carboxylate;
• (b) reacting the product of step (a) with a compound of formula ROCH.sub.3, wherein R is a mental;
• and,
• (c) reacting the product of step (b) with a compound of formula (III);
• or
• iii) (a) cyclising a compound of formula (IX):
• ##STR33## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined above, and reacting the product formed with either trimethyl orthofornate or a dimethoxymethyl carboxylate;
• (b) reacting the product of step (a) with a compound of formula ROCH.sub.3, wherein R is a metal;
• and,
• (c) reacting the product of step (b) with a compound of formula (III).