Abstract

The reaction of cyanothioacetamide with ethoxymethylenemalonate and triethylamine in ethanol upon heating is non-selective and leads to the formation of a mixture of triethylammonium 1,5-diamino-2,4-dicyano-5-thioxopenta-1,3-diene-1-thiolate and triethylammonium 6-oxo-3-cyano-5-ethoxycarbonyl-1H-pyridin-2-thiolate with a predominance of the latter. When treating with primary amines and 37% formalin in boiling aqueous alcohol, the reaction product gives only 4-(1,3,5-thiadiazinan-2-ylidene)-2-(3,4-dihydro-2H-1,3,5-thiadiazin-6-yl)pent-2-enedinitrile instead of the expected pyrido[2,1-b][1,3,5]thiadiazine derivatives. Triethylammonium 6-oxo-3-cyano-5-ethoxycarbonyl-1H-pyridin-2-thiolate does not react under these conditions.

中文翻译：

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三乙胺存在下乙氧基丙二酸丙二酸酯与氰基硫代乙酰胺的反应：1,5-二氨基-2,4-二氰基-5-硫代己酸酯-1,3-二烯-1-硫醇盐的形成和未预期的氨甲基化结果

摘要

氰基硫代乙酰胺与乙氧基亚甲基丙二酸酯和三乙胺在乙醇中加热时的反应是非选择性的，并导致形成三乙基铵1,5-二氨基-2,4-二氰基-5-硫代己烯-1,3-二烯-1-硫醇盐和6-乙氧基-3-氰基-5-乙氧基羰基-1 H-吡啶-2-硫醇盐的三乙铵，其中后者占优势。用沸腾的乙醇水溶液中的伯胺和37％福尔马林处理时，反应产物仅生成4-（1,3,5-噻二嗪南-2-亚烷基）-2-（3,4-二氢-2 H -1,3 ，而不是预期的吡啶并[2,1- b ] [1,3,5]噻二嗪衍生物。在这些条件下，6-乙氧基-3-氰基-5-乙氧基羰基-1 H-吡啶-2-硫醇三乙铵不反应。