A synthesis of new 7-amino-substituted 4-aminopyrazolo[1,5-a][1,3,5]triazines via a selective three-component triazine ring annulation

• Main Authors: Lim, Felicia Phei Lin, Luna, Giuseppe, Tan, Khai Ching, Tiekink, Edward R. T. *, Dolzhenko, Anton V
• Format: Article
• Language: English
• Published: Elsevier 2019
• Subjects: QD Chemistry
• Online Access: http://eprints.sunway.edu.my/1022/1/Tiekink%20A%20synthetis%20of%20new%207%20amino%20substituted%20Tetrahedron%202019%2075%202322.pdf; http://eprints.sunway.edu.my/1022/; http://doi.org/10.1016/j.tet.2019.03.002
• Institution: Sunway University

3-Amino-substituted 5-aminopyrazoles were found to be suitable substrates for the synthesis of new 4-aminopyrazolo[1,5-a][1,3,5]triazines (5-aza-9-deaza-adenines) when used in the one-pot, three-component reaction with cyanamide and triethyl orthoformate under microwave irradiation. The reaction proceeded selectively and its scope was demonstrated by the preparation of a library of 4-aminopyrazolo[1,5-a][1,3,5]triazines. Some structural aspects of the prepared compounds were investigated using dynamic NMR spectroscopy and X-ray crystallography. The operational simplicity, short reaction time, and good reproducibility are attractive features of the developed robust and practical approach for the synthesis of 7-amino-substituted 4-aminopyrazolo[1,5-a][1,3,5]triazines.