RUDN University chemists proposed a one-step method for the synthesis of 1,3,5-triazinanes - promising objects for industrial and medicinal chemistry. Unlike traditional approaches, the new method does not require hard-to-find reagents or complex equipment. In addition, the reaction takes place under mild conditions and with good yield. The results were published in Tetrahedron.
Newswise — Triazinanes are a group of chemical compounds in which three carbon atoms are replaced by nitrogen atoms in their six-membered rings and have a wide range of biological activity. The most popular and widespread are 1,3,5-triazinanes, in which carbon and nitrogen atoms alternate. Such compounds are used, for example, to create anticonvulsants or herbicides. Moreover, the structure of triazinanes itself is attractive for chemical research - they can be building blocks for creating more complex molecules. To obtain triazinanes, various methods have been developed, but most of them are multi-step, based on complex starting materials, and require heating, during which the target product is partially destroyed. As a rule, symmetrical products are formed. RUDN University chemists have proposed the simplest method for obtaining bicyclic triazinanes.
“Most syntheses of the 1,3,5-triazine ring involve approaches based on the simplest aldehydes and amines. Such approaches typically involve heating reactants, most often in benzene. It usually leads to undesirable thermal decomposition of the starting materials and products, so it is advisable to use lower temperatures. The second key problem in the synthesis of triazinanes is the formation of symmetrical products,” Fedor Zubkov, PhD, Associate Professor of the Department of Organic Chemistry of the RUDN University said.
Chemists have proposed a method for the synthesis of triazinanes using the one-pot principle. Three different reagents are mixed, after which they sequentially react with each other to form the desired product. This approach is distinguished by the fact that there is no need for isolation and purification of intermediate products. The new method required three readily available reagents: diamine, sulfonamide, and three molecules of formaldehyde. All obtained classes of framework nitrogen compounds were studied using X-ray diffraction analysis.
Using a new method, RUDN University chemists obtained four series of compounds starting from different diamines. The authors selected the optimal reaction conditions - boiling chloroform (boiling point is 61°C) in the presence of magnesium perchlorate as a catalyst. The yield of target products reaches 78%. In addition, chemists managed to obtain previously unknown structures. They can become new building blocks for organic synthesis.
“The procedure we propose is simple from an experimental point of view. It does not require complex equipment for synthesis or chromatography for purification and isolation of the product,” Fedor Zubkov, PhD, Associate Professor of the Department of Organic Chemistry of the RUDN University said.
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