A New One-Pot Three-Component Synthesis of 4-Aryl-6-cycloamino-1,3,5-triazin-2-amines under Microwave Irradiation
| Autor: | Anton V. Dolzhenko, Muhammad Syafiq Bin Shahari, Ahmad Junaid, Edward R. T. Tiekink |
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| Rok vydání: | 2021 |
| Předmět: |
010405 organic chemistry
Aryl Organic Chemistry Hydrochloric acid Crystal structure Alkali metal 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine chemistry 030220 oncology & carcinogenesis Microwave irradiation Dehydrogenation Cyclic amines |
| Zdroj: | Synthesis. 53:2457-2468 |
| ISSN: | 1437-210X 0039-7881 |
| Popis: | A new method for the fast synthesis of diverse 4-aryl-6-cycloamino-1,3,5-triazin-2-amines was developed. The synthesis is performed under microwave irradiation in a one-pot manner from cyanoguanidine, aromatic aldehydes, and cyclic amines. Their three-component reaction in the presence of hydrochloric acid produced dihydrotriazines, which were then converted (without isolation) into the targeted compounds via aromatic dehydrogenation in the presence of alkali. The reaction tolerated various aromatic aldehydes (including heterocyclic) and cyclic amines. Crystal structures of two representative 4-aryl-6-morpholino-1,3,5-triazin-2-amines were established by X-ray crystallography. The results of preliminary biological screening identified potent antileukemic activity for 6-[3,4-dihydroisoquinolin-2(1H)-yl]-4-phenyl-1,3,5-triazin-2-amine. |
| Databáze: | OpenAIRE |
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