Process for the preparation of o-carboxypyridyl- and o-carboxyquinolylimidazolinones

Claim 1

A method for the preparation of o-carboxypyridiyl- and o-carboxyquinolylimidazolinones of formula I ##STR20## wherein X is OR 3 and or NR 4 R 5 ; Y is hydrogen, halogen, or C 1 -C 6 alkyl optionally substituted by one or two C 1 -C 4 alkoxy groups; Z is hydrogen; and when Y and Z are taken together with the carbons to which they are attached, they may form a ring in which YZ is --CH═CH--CH═CH--; R 1 and R 2 are C 1 -C 4 alkyl or when taken together they may represent C 3 -C 6 cycloalkyl optionally substituted with methyl and when R 1 and R 2 are not the same, the optical isomers thereof; R 3 is C 1 -C 6 alkyl, C 5 -C 6 cycloalkyl or benzyl optionally substituted by one or two C 1 -C 6 alkyl, C 1 -C 4 alkoxy, or halo; R 4 and R 5 are C 1 -C 4 alkyl, or when taken together with the nitrogen to which they are attached, they may represent piperidinyl or morpholinyl; comprising reacting a compound of formula II ##STR21## wherein X, Y and Z are as described hereinabove for formula I; with one equivalent of a compound of formula III ##STR22## wherein R 1 and R 2 are as described above for formula I; in the presence of about 50-300 weight%, based on the weight of the compound of formula II, of an aromatic solvent and in the presence of about 5.5-9.0 molar equivalents of sulfur at a temperature range of about 100° C. to 200° C.

Claim 2

A method for the preparation of o-carboxypyridiyl- and o-carboxyquinolylimidazolinones of formula I ##STR20## wherein X is OR 3 and or NR 4 R 5 ; Y is hydrogen, halogen, or C 1 -C 6 alkyl optionally substituted by one or two C 1 -C 4 alkoxy groups; Z is hydrogen; and when Y and Z are taken together with the carbons to which they are attached, they may form a ring in which YZ is --CH═CH--CH═CH--; R 1 and R 2 are C 1 -C 4 alkyl or when taken together they may represent C 3 -C 6 cycloalkyl optionally substituted with methyl and when R 1 and R 2 are not the same, the optical isomers thereof; R 3 is C 1 -C 6 alkyl, C 5 -C 6 cycloalkyl or benzyl optionally substituted by one or two C 1 -C 6 alkyl, C 1 -C 4 alkoxy, or halo; R 4 and R 5 are C 1 -C 4 alkyl, or when taken together with the nitrogen to which they are attached, they may represent piperidinyl or morpholinyl; comprising reacting a compound of formula II ##STR21## wherein X, Y and Z are as described hereinabove for formula I; with one equivalent of a compound of formula III ##STR22## wherein R 1 and R 2 are as described above for formula I; in the presence of about 50-300 weight%, based on the weight of the compound of formula II, of an aromatic solvent and in the presence of about 5.5-9.0 molar equivalents of sulfur at a temperature range of about 100° C. to 200° C.