Verfahren zur Herstellung von neuen 2,3-Dihydro-5H-imidazo[2,1-a]isoindolderivaten und ihren Salzen

摘要

1,232,469. Imidazo-isoindoles. SANDOZ Ltd. 14 Aug., 1968 [15 Aug., 1967; 3 May, 1968], No. 38930/68. Addition to 1,225,411. Heading C2C. Novel compounds have the Formula (III) in which R, R 1 and R 2 signify hydrogen, chlorine, fluorine trifluoromethyl, a straight-chain alkyl radical of 1 to 4 carbon atoms or a straightchain alkoxy radical of 1 to 4 carbon atoms, provided that (1) R, R 1 and R 2 are such that there is never trifluoromethyl on each of two adjacent carbon atoms, and (2) when R or R 2 is trifluoromethyl, R 1 is hydrogen, chlorine or fluorine, R 3 , R 4 and R 5 signify hydrogen, chlorine or fluorine, and R 6 is hydrogen or fluorine, with the further provisos that not more than 2 of R 3 , R 4 , R 5 and R 6 are other than hydrogen, and not more than 3 of R, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are other than hydrogen. The compounds are prepared by reducing a compound (II) with lithium aluminium hydride in an inert ether solvent under an inert atmosphere. Compounds (I) are obtained by a process comprising contacting III with air or oxygen. The following starting materials and intermediates are also described and exemplified: 2 - iodo - 4 - and - 5 - chloro - toluenes, 2 - iodo- 4 - fluorotoluene; 5 - fluoro - and 4 - and 5- chloro - o - toluic acids; 2 - methyl - (4,5 - dichloro-, -5-fluoro-, -4,41,5-trichloro-, -4-chloro- and - 5 - chloro) - benzophenones; 2 - benzoyl- (4-chloro-, -5-chloro-, -4-fluoro- and -4,5-dichloro)- benzoic acids, 2 - (p - chlorobenzoyl) - 4,5 - dichlorobenzoic acid, and 2-(31-trifluoromethylbenzoyl) -, 2 - (31 - -fluorobenzoyl) - and 2 - (3,5 - dichlorobenzoyl)-benzoic acids. Compounds IV made, e.g. by reacting the benzoic acids with ethylene diamine are converted into compounds II by hydrogenation.