Verfahren zur Herstellung ll-basisch substituierter 5 H-Dibenzo[b,e],[1,4] diazepine

摘要

Compounds (some of which are novel) of the general formula (wherein -Z- represents -S-, -SO- or -(N-R6)-, R6 being hydrogen, a C1-5 alkyl or C2- 5 alkenyl group, R2 and R3, which may be the same or different, represent hydrogen atoms, C1- 5 alkyl, C2- 5 alkenyl or amino groups, mono-or di-alkylamino or mono- or di-alkylaminoalkyl groups in which the alkyl groups each contain 1-3 carbon atoms, or monocyclic aryl or aralkyl groups optionally substituted with halogen atoms or OH, CF3 or C1- 3 alkyl, alkoxy or alkymercapto groups, or R2 and R3 together with the adjacent nitrogen atom form a monocyclic alkyleneimino radical optionally containing further O-, S- or N-hetero-atoms, the last of which carries a hydrogen atom or an alkyl, hydroxyalkyl or alkoxyalkyl group of up to 3 carbon atoms, and R4 and R5, which may be the same or different, represent hydrogen or halogen atoms or OH, CF3 or C1- 3 alkyl, alkoxy or alkylmercapto groups) are prepared by (a) treating a reaction mixture containing nitrilium or imonium cations of the general formulae (wherein -Z- represents -S-, -SO- or -(N-R6)-, R6 being hydrogen, a C1- 5 alkyl or C2- 5 alkenyl group or a protecting group) with ammonia or an amine (R2NHR3), or (b) cyclizing an amide or thioamide of the general formula (wherein R represents S or O, and Z has the same meaning as Z1 in (a)), and in either case subsequently removing the protecting group R6 if present. When R2 and/or R3 in the products are hydrogen, they may be replaced by other R2/R3 values by the action of reactive esters of compounds R2OH or R3OH. Similarly an -NH- group as -Z- may be reacted with a reactive ester of R1OH. When -Z- is -S- it may be oxidized to -SO-. The bases obtained may be converted to acid addition salts or, when tertiary, to quaternary ammonium derivatives. Amides and thioamides of the last general formula above are prepared by reducing the corresponding nitro compounds.