GB1258946A - - Google Patents

Abstract

1,258,946. Imidazole and imidazaloindole derivatives. AMERICAN HOME PRODUCTS CORP. 6 May, 1970 [6 May, 1969], No. 23039/69. Heading C2C. Compounds of formulµ wherein R 1 is phenyl, monohalophenyl, dihalophenyl, mono(C 1-6 )alkylphenyl, di(C 1-6 )alkylphenyl, trifluoromethylphenyl, mono(C 1-6 )-alkoxyphenyl, di(C 1-6 )alkoxyphenyl, thienyl, pyridyl, furyl or tetrahydro-2-naphthyl ; R 2 is hydrogen, halogen, amino, C 1-6 alkylamino, C 1-6 alkyl or C 1-6 alkoxy; R 3 is hydrogen when R 2 and R 3 are dissimilar and when R 2 and R 3 are the same they are both selected from hydrogen, halogen, C 1 _ 6 alkyl and C 1 _ 6 alkoxy; and R 4 is C 1-6 alkyl, phenyl, monohalophenyl, dihalophenyl, mono(C 1-6 )alkylphenyl, di(C 1-6 )-alkylphenyl or C 1-6 alkoxyphenyl are prepared by contacting an o-ketoacid of the formula with a monosulfonylethylenediamine of the formula at a temperature range of about 180‹ to about 225‹ C. for a period of about one-half to about one hour to obtain a compound of Formula III ; and if desired the 9b-tetrahydro-5H-imidazo- [2,1-a]isoindol-5-one product of Formula III is hydrolysed and rearranged by admixture with from about 80 to about 100% sulphuric acid to give an imidazolinyl phenyl carbonyl compound of general Formula (IV) which is recovered by conventional means, or the reaction mixture containing compound (IV) is neutralized by addition of a base and the precipitate recrystallized to afford a dihydroimidazoisoindolol of general Formula (V). The compounds of Formula (V) have antidepressant and appetite suppressant activity.