The aldehydes VIa and VIb were transformed by treatment with chloroform and sodium hydroxide in the presence of triethylbenzylammonium chloride to the α-chloro acids VIIa and VIIb which were demethylated with boron tribromide and the products were cyclized with sodium hydroxide in dimethyl sulfoxide to 2-fluoro-6H-dibenz[b,e]-1,4-oxathiepin-6-carboxylic acids Ia and Ib. Syntheses of the aldehydes XVIIbcd were carried out and the products treated with 1-methyl-4-piperidylmagnesium chloride to give the amino alcohols XVIbcd. Cyclizations with sodium hydride in dimethylformamide afforded the title compounds XIIbcd; compounds XVIIIbc and XIX were isolated as by-products and characterized. Compound XIIb was transformed via the secondary amine XIIIb to the amino alcohol XIVb which was esterified to the decanoate XVb. Substances XIIbcd are highly active neuroleptic agents with an important prolongation of the central depressant effect. The decanoate XVb revealed the properties of a medium long acting depot neuroleptic.
醛类化合物VIa和VIb经氯仿和氢氧化钠处理,在三乙基苄基氯化铵存在下转化为α-氯代酸VIIa和VIIb,然后用三溴化硼去甲基化,再在二甲基亚砜中用氢氧化钠进行环化反应,得到2-氟-6H-二苯[b,e]-1,4-噁硫杂环己酸Ia和Ib。合成醛类化合物XVIIbcd,并用1-甲基-4-哌啶基镁氯化物处理,得到氨基醇XVIbcd。在二甲基甲酰胺中用氢化钠环化,得到目标化合物XIIbcd;化合物XVIIIbc和XIX作为副产物被分离和鉴定。化合物XIIb经次胺XIIIb转化为氨基醇XIVb,再酯化为癸酸盐XVb。化合物XIIbcd是高活性的神经阻滞剂,具有重要的中枢抑制效果延长作用。癸酸盐XVb表现出中等长效的缓释神经阻滞剂特性。