Three new series of 3-(substituted)methylthio-4-cyano-5,6,7,8-tetrahydroisoquinolines were designed and synthesized starting from readily available materials, 7-acetyl-4-cyano-1,6-dimethyl-6-hydroxy-8-(4-pyridyl, 3-pyridyl, phenyl, 4-methoxyphenyl, or 4-chlorophenyl)-5,6,7,8-tetrahydrosoquinoline-3(2H)-thiones 2a–e in high yields and very pure states. Thus, compounds 2a–e were reacted with some chloro reagents, namely, N-aryl-2-chloroacetamides 3a–f and N-(naphthalen-2-yl)-2-chloroacetamide (3g) under mild basic conditions to give the first two series of the target compounds, 3-(N-aryl)carbamoylmethylthio-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles 4a–l and 5a–e, respectively. Reaction of compounds 2d,e with ethyl chloroacetate under the same conditions gave the other series, 3-ethoxycarbonyl-methylthio-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles 6d,e. Structural formulas of all of the new compounds were elucidated and confirmed by elemental and spectral analyses. The insecticidal activity of all synthesized 5,6,7,8-tetrahydrosoquinolines toward the nymphs and adults of Aphis gossypii were screened. The results revealed the promising insecticidal activity of some tested compounds. Moreover, the structure–activity relationships as well as molecular docking of some representative compounds were evaluated.

中文翻译：

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吡啶衍生物作为杀虫剂：第 6 部分。3-（取代）甲硫基-5,6,7,8-四氢异喹啉-4-甲腈对棉蚜的设计、合成、分子对接和杀虫活性（Glover，1887）


以容易获得的材料 7-乙酰基-4-氰基-1,6-二甲基-6-为原料，设计并合成了三个新系列的 3-(取代)甲硫基-4-氰基-5,6,7,8-四氢异喹啉。羟基-8-(4-吡啶基、3-吡啶基、苯基、4-甲氧基苯基或4-氯苯基)-5,6,7,8-四氢异喹啉-3(2 H )-硫酮2a – e ，产率高，产率高纯粹的状态。因此，化合物2a – e与一些氯试剂，即N-芳基-2-氯乙酰胺3a – f和N- (萘-2-基)-2-氯乙酰胺( 3g )在温和碱性条件下反应，得到第一个两个系列的目标化合物，分别为3-( N-芳基)氨基甲酰基甲硫基-5,6,7,8-四氢异喹啉-4-甲腈4a – l和5a – e 。化合物2d 、 e与氯乙酸乙酯在相同条件下反应，得到另一系列3-乙氧基羰基-甲硫基-5,6,7,8-四氢异喹啉-4-甲腈6d 、 e 。所有新化合物的结构式均通过元素和光谱分析得到阐明和证实。筛选了合成的5,6,7,8-四氢喹啉对棉蚜若虫和成虫的杀虫活性。结果揭示了一些测试化合物具有良好的杀虫活性。此外，还评估了一些代表性化合物的构效关系以及分子对接。