Dibenzo[b,f]-1,4-thiazepin-11(10H)-ones IIa-IIc reacted with phosphorus pentasulfide in pyridine under the formation of the thiones IIIa-IIIc which were transformed by treatment with hydrazine hydrate in 1-butanol to the hydrazine derivatives IVa-IVc. Reactions with triethyl orthoformate in ethanol in the presence of sulfuric acid effected cyclization to dibenzo[b,f]-1,2,4-triazolo[4,3-d]-1,4-thiazepine (Va) and its chloro derivatives Vb, Vc which were treated with bromine in a boiling mixture of chlorofom and pyridine and gave the 3-bromo derivatives VIa-VIc. The title compounds Ia-Ic were obtained by substitution reactions with an excess of boiling 1-methylpiperazine. An attempt at preparing an analogous 14H-dibenzo[b,g]-1,2,4-triazolo[4,3-d]-1,4-thiazocine derivative was discontinued in the stage of reaction of the thione X with hydrazine hydrate which resulted in the azine XI. Compounds Ia-Ic on intravenous administration are highly toxic and inactive in tests for CNS effects; compound Ic showed a clear anticholinergic activity.
Dibenzo[b,f]-1,4-thiazepin-11(10H)-ones IIa-IIc 在吡啶中与五硫化磷反应,形成了硫代酮IIIa-IIIc,随后在1-丁醇中用肼水合物处理,转化为肼衍生物IVa-IVc。在乙醇中存在硫酸的情况下,与三乙基正甲酸酯反应,发生环化反应生成了dibenzo[b,f]-1,2,4-三唑并[4,3-d]-1,4-噻吩(Va)及其氯衍生物Vb、Vc,随后用溴在氯仿和吡啶的沸腾混合物中处理,得到3-溴衍生物VIa-VIc。通过过量沸腾的1-甲基哌嗪进行置换反应,得到了标题化合物Ia-Ic。试图制备类似的14H-dibenzo[b,g]-1,2,4-三唑并[4,3-d]-1,4-噻吩环衍生物的尝试在硫代酮X与肼水合物反应阶段中中止,结果形成了偶氮化合物XI。化合物Ia-Ic在静脉注射后具有高毒性,并且在中枢神经系统效应测试中无活性;化合物Ic显示出明显的抗胆碱能活性。