IMIDAZOLES AND PROCESSES FOR THEIR PRODUCTION

摘要

1474630 2-Heterocyclic substituted imidazoles CIBA GEIGY AG 9 Aug 1974 [13 Aug 1973] 35224/74 Heading C2C [Also in Division A5] Novel compounds of the Formula I wherein one of R 1 and R 2 is hydrogen or alkyl and the other is nitro, R 3 is alkyl, R 4 is oxo or thioxo, X is carbonyl, thiocarbonyl, sulphinyl or sulphonyl and when X is carbonyl, R 5 is alkoxy, amino, alkylamino, dialkylamino, piperidino, morpholino or pyrrolidino, and when X is thiocarbonyl, sulphinyl or sulphonyl R 5 is alkyl, phenyl optionally substituted by one or more alkyl, alkoxy, halogen or trifluoromethyl amino, alkylamino, dialkylamino piperidino or pyrrolidino, and alk is 1,2- ethylene, wherein alkyl groups have up to 7 carbon atoms, and their salts may be prepared by (a) reacting a compound of the Formula II wherein Z is methyl sulphonyl or methyl sulphinyl with a compound of the Formula III (b) reacting a compound of the Formula IV with O : C : NCH 3 to form a compound I in which X is carbonyl and R 5 is methylamino, and if desired, a resulting compound I, in which R 2 is nitro and R 1 is hydrogen, is rearranged by treatment with an alkali metal iodide to a compound I in which R 2 is hydrogen and R 1 is nitro, and/or, if desired, separating racemates, forming salts or converting salts into free compounds. Intermediates of the Formula III are prepared by reacting ethylene urea with various isocyanates, isothiocyanates or acid halides or reacting 1 - chlorocarbonyl - 2 - oxo tetrahydroimidazole with morpholine. The compounds of the Formula I in addition to their pharmaceutical use (see A5B abridgment) may be used to protect materials from bacterial or other microbial deterioration.