5-ARYL-2,3-DIHYDRO-2,2(OR 3,3)DIMETHYL-5H-IMIDAZO(2,1-A)ISOINDOL-5-OLS AND 2-(4,4(OR 5,5)DIMETHYL-2-IMIDAZOLIN-2-YL)-BENZOPHENONE ACID ADDITION SALTS AND PROCESSES FOR THEIR PREPARATION

摘要

1325066 N - [2 - (3 - Hydroxy - 2 - phthalimidinyl) - ethyl] - sulphonamides AMERICAN HOME PRODUCTS CORP 2 Oct 1970 [12 Feb 1970] 20997/72 Divided out of 1325065 Heading C2C Novel N - [2 - (3 - Hydroxy - 2 - phthalimidinyl)-ethyl]-sulphonamides of the general formula wherein RSP1/SP is a phenyl, monohalophenyl, dihalophenyl, mono-C 1-5 alkylphenyl, di-C 1-5 alkylphenyl, trifluoromethylphenyl, mono- C 1-6 alkoxyphenyl, di-C 1-6 alkoxyphenyl, thienyl, pyridyl, furyl or 5,6,7,8-tetrahydro- 2-naphthyl group; RSP2/SP is a hydrogen or halogen atom or an amino, C 1-5 alkylamino, C 1-5 alkyl or C 1-6 alkoxy group; RSP3/SP is a hydrogen atom when RSP2/SP and RSP3/SP are dissimilar and when RSP2/SP and RSP3/SP are the same they are both a hydrogen or halogen atom or a C 1-5 alkyl or C 1-6 alkoxy group; RSP4/SP and RSP5/SP are both a hydrogen atom or C 1-5 alkyl group; and RSP6/SP is a C 1-5 alkyl-, phenyl-, mono- or di-halophenyl-, mono- or di-C 1-5 alkylphenyl- or C 1-6 alkoxyphenyl-sulphonyl group, are prepared by reaction of an amine of the first general formula above wherein RSP6/SP is a hydrogen atom with a sulphonyl halide of the general formula RSP6/SPX, wherein X is a halogen atom. When RSP4/SP and RSP5/SP are hydrogen atoms, they may be treated with a strong acid to give 5 - aryl - 2,3 - dihydro - 5H - imidazo[2,1-a]- isoindol-5-ols of the general formula or their tautomeric acid addition salts of the general formula wherein HX is an acid. Amines of the first general formula above wherein RSP6/SP is a hydrogen atom are prepared (a) by hydrolysis of an imidazoisoindolone of the general formula or (b) by reaction of a benzofuranone of the general formula with a diamine of the general formula Imidazoisoindolones of the third general formula above are prepared by reaction of a benzoic acid of the general formula with a diamine of the fifth general formula above.