Spiro-tetraline succinimide compounds

摘要

1,133,012. Spirotetraline succinimide derivatives. ASTRA A.B. 12 July, 1966 [17 Sept., 1965], No. 31303/66. Heading C2C. [Also in Division A5] Novel spiro compounds of formula wherein R1 is H, halogen, C 1-4 alkyl, C 1-4 alkoxy or OH, R2 and R3 are H, OH, C 1-4 alkyl or C 1-4 alkoxy, R4 is a bivalent saturated hydrocarbon radical containing at most 6 carbon atoms and Am is pyrrolidino, piperidino, morpholino or wherein R5 is H or C 1-4 alkyl and R6 is H, OH or C 1-6 alkoxy and m is 1-4 when R6 is H or 2 to 4 when R6 is OH or alkoxy or R4 and Am together represent the group and acid addition salt thereof are prepared by reacting a compound of formula with a compound of formula Z-R4-A in which formulµ A is Am or a group convertible thereinto in a manner known per se and one of X, Y and Z is amino, the others being OH, alkoxy, halogen, amino or -O-tosyl or when 2 is amino X and Y together are -O- or when Z is halogen X and Y together are-NH- with optional conversion of A and/or salt formation and/or resolution of epimers. Intermediates shown in the following reaction scheme are prepared in the first step by the Knrevengal condensation with malononitrile, in the second step with NaCN and ethanol and in the third step by hydrolysis: N - (# - Bromoethyl) - spirotetraline succinimide is prepared by reaction of 1,2-dibromoethane and the imide. N - (γ- Tosyloxypropyl) - spirotetraline succinimide is obtained by tosylation of theγ-hydroxypropyl compound which was itself prepared by reaction of the anhydride XIII above R1=R2= R3=H and 3-aminopropanol.