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Über in 6‐Stellung basisch substituierte Morphanthridine. 8. Mitteilung über siebengliedrige Heterocyclen
Author(s) -
Hunziker F.,
Künzle F.,
Schmutz J.
Publication year - 1966
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19660490502
Subject(s) - chemistry , benzophenone , hydrolysis , substituent , medicinal chemistry , stereochemistry , organic chemistry
Abstract Morphanthridines III with a basic substituent in position 6, which show neuroleptic activity, have been synthesised as follows: Chlorination of the lactams I with POCl 3 gave the iminochlorides II, which were converted by bases to the amidines III. The 11‐oxo‐morphanthridines VI and VII were synthesised using the same procedure, 2‐(1‐methylpiperazine‐4‐carbonyl)‐2′‐amino‐benzophenone (XI) was obtained directly from the 6‐chloro‐11‐oxo‐morphanthridine (V) or by extended heating of VI with N‐methylpiperazine. Reduction of the 11‐oxo‐compounds VI and VII with NaBH 4 gave the 11‐hydroxy‐compounds IX and X. 3‐(2‐aminophenyl)‐phtalide (VIII) resulted from the acid hydrolysis of IX.