A New Approach to the Synthesis of 4H-1,3,5-Oxadiazine Derivatives

Q3 Biochemistry, Genetics and Molecular Biology

Biointerface Research in Applied Chemistry Pub Date : 2022-10-31 DOI:10.33263/briac134.379

引用次数: 1

Abstract

Derivatives of 1,3,5-oxadiazine are of great interest as potential biologically active compounds. In this work, we report on a new method for synthesizing 1,3,5-oxadiazine derivatives. The method is based on the elimination of hydrogen sulfide from N-((1-carboxamido-2,2,2-trichloroethyl)carbamothioyl)benzamides by the action of dicyclohexylcarbodiimide (DCC). Presumably, at the first stage of the transformation, an intermediate carbodiimide is formed, which then enters into the [4+2] cycloaddition reaction with another DCC molecule to form the final products - N-(2,2,2-trichloro-1-(((2Z,4E)-3-cyclohexyl-2-(cyclohexylimino)-6-phenyl-2,3-dihydro-4H-1,3,5-oxadiazin-4-ylidene)amino)ethyl)carboxamides. Target products were obtained in 68-89% yields. The structure of the obtained compounds was confirmed by IR, 1H NMR, 13C NMR spectroscopy, and mass spectrometry.

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合成4h -1,3,5-恶二嗪衍生物的新方法

1，3，5-恶二嗪衍生物作为一种潜在的生物活性化合物而备受关注。本文报道了一种合成1,3,5-恶二嗪衍生物的新方法。该方法基于通过二环己基碳二亚胺（DCC）的作用从N-（（1-甲酰胺-2,2,2-三氯乙基）氨基甲硫基）苯甲酰胺中消除硫化氢。据推测，在转化的第一阶段，形成中间体碳二亚胺，然后与另一个DCC分子进行[4+2]环加成反应，形成最终产物-N-（2,2,2-三氯-1-（（（2Z，4E）-3-环己基-2-（环己基氨基）-6-苯基-2,3-二氢-4H-1,3,5-恶二嗪-4-亚基）氨基）乙基）羧酰胺。以68-89%的产率获得目标产物。通过IR、1H NMR、13C NMR光谱和质谱来确认所获得的化合物的结构。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Biointerface Research in Applied Chemistry CHEMISTRY, APPLIED-

CiteScore

4.80

自引率

0.00%

发文量

256

期刊介绍： Biointerface Research in Applied Chemistry is an international and interdisciplinary research journal that focuses on all aspects of nanoscience, bioscience and applied chemistry. Submissions are solicited in all topical areas, ranging from basic aspects of the science materials to practical applications of such materials. With 6 issues per year, the first one published on the 15th of February of 2011, Biointerface Research in Applied Chemistry is an open-access journal, making all research results freely available online. The aim is to publish original papers, short communications as well as review papers highlighting interdisciplinary research, the potential applications of the molecules and materials in the bio-field. Our aim is to encourage scientists to publish their experimental and theoretical results in as much detail as possible.