New One-Pot Synthesis of 1,3,5-Triazines: Three-Component Condensation, Dimroth Rearrangement, and Dehydrogenative Aromatization.,ACS Combinatorial Science

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New One-Pot Synthesis of 1,3,5-Triazines: Three-Component Condensation, Dimroth Rearrangement, and Dehydrogenative Aromatization.
ACS Combinatorial Science Pub Date : 2019-06-10 , DOI: 10.1021/acscombsci.9b00079
Ahmad Junaid ₁ , Felicia Phei Lin Lim ₁ , Edward R T Tiekink ₂ , Anton V Dolzhenko _{1,

3}

Affiliation

A new, effective one-pot synthesis of the 6, N2-diaryl-1,3,5-triazine-2,4-diamines under microwave irradiation was developed. The method involved an initial three-component condensation of cyanoguanidine, aromatic aldehydes, and arylamines in the presence of hydrochloric acid. Without isolation, the resulting 1,6-diaryl-1,6-dihydro-1,3,5-triazine-2,4-diamines were treated with a base to initiate Dimroth rearrangement and spontaneous dehydrogenative aromatization, affording the desired compounds. The developed method was found to be sufficiently general in scope, tolerating various aromatic aldehydes and amines; by using their combinations in the first step, a representative library of 110 compounds was successfully prepared and screened for anticancer properties.

中文翻译：

1,3,5-三嗪的新的一锅合成：三组分缩合，Dimroth重排和脱氢芳构化。

开发了一种在微波辐射下有效合成一锅6，N2-二芳基-1,3,5-三嗪-2,4-二胺的新方法。该方法涉及在盐酸存在下氰基胍，芳族醛和芳基胺的初始三组分缩合。不经分离，将所得的1，6-二芳基-1，6-二氢-1，3，5-三嗪-2，4-二胺用碱处理以引发Dimroth重排和自发脱氢芳构化，得到所需化合物。发现所开发的方法在范围上足够通用，可以耐受各种芳族醛和胺。通过在第一步中使用它们的组合，成功制备了110种化合物的代表性文库，并筛选了其抗癌特性。

更新日期：2019-06-10

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