Collect. Czech. Chem. Commun. 1984, 49, 603-620

Reactions of 4,4'-disubstituted diphenyl sulfides with chloroacetyl chloride and aluminium chloride

Jiří Jílek, Josef Pomykáček, Jiří Holubek, Emil Svátek, Miroslav Ryska, Jiří Protiva and Miroslav Protiva

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


Reactions of 4,4'-dihalogenodiphenyl sulfides IIIa-IIIc with chloroacetyl chloride and aluminium chloride afforded the enol forms of 2,8-dihalogeno-11-(chloroacetyl)dibenzo[b,f]thiepin-10(11H)-ones IVa-IVc. A similar reaction of di(4-methylphenyl) sulfide (IIId) resulted in 9-(chloromethylene)-2,7-dimethylthioxanthene (Vd) as the main product. Substitution reactions of IVa with piperidine and 1-methylpiperazine gave compounds VI and VII with the unchanged chelate system of the starting substance. A stepwise methylation of (2-phenylthiophenyl)acetonitrile resulted in the monomethyl derivative XVI and the dimethyl derivative XVII which afforded by alkaline hydrolysis the acids XVIII and XIX. Attempts at their cyclization with polyphosphoric acid to the corresponding 11-methylated dibenzo[b,f]thiepin-10(11H)ones are described.