Die Thiophenole (I) reagieren mit dem Nitril (II) zu den Arylthjoacetonitrilen (III), die in die Titelverbindungen (IV) bzw. deren Hydro‐ Chloride übergeführt werden.
The synthesis of a series of 6-fluoro-10-piperazino-10,11-dihydrodibenzo[b,f]thiepins Ic-IIIc, Vc and VIc is described; these compounds are derivatives of the neuroleptic agents perathiepin (Ia), octoclothepin (IIIa), doclothepin (Va) and their hydroxyethyl analogues IIa and VIa in which the metabolic hydroxylation to position 6 was made impossible by blockade. The synthesis used common procedures via the intermediates VII-XVIII. Fluorination in position 6 does not influence much the pharmacological profile of the compounds indicating that hydroxylation in position 6 is only a minor metabolic pathway. The most interesting substance is the 6-fluoro derivative of octoclothepin (IIIc) which is a potent central depressant and neuroleptic agent with some protraction of the sedative effects.
Die aus den IO‐Bromdibenzothiepinen (Ia) und (Ib) erhältlichen Nitrile (IIa) und (IIb) lassen sich zu den Dihydroverbindungen (III) reduzieren, wobei nach längerer Reaktionszeit auch die entsprechenden Carboxamide (IV) entstehen, die zu den Carbonsäuren hydrolysiert werden.
Reactions of thiophenol and 16 of its derivatives with chloroacetonitrile afforded arylthioacetonitriles IVb-XXb which were treated with hydroxylamine and gave arylthioacetamidoximes IVa-XXa. Compounds VIIa-IXa, XIIa, XVIa and XVIIIa exhibited antireserpine activity in the test of ptosis in mice and compounds IXa and XVIIa in the test of reserpine hypothermia in mice.
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