A multicomponent reaction of 2-aminoimidazoles: microwave-assisted synthesis of novel 5-aza-7- deaza-adenines†‡

• Main Authors: Lim, Felicia Phei Lin, Low, Szy Teng, Ho, Elvina Lee King, Halcovitch, Nathan R., Tiekink, Edward R. T. *, Dolzhenko, Anton V
• Format: Article
• Language: English
• Published: Royal Society of Chemistry 2017
• Subjects: QD Chemistry
• Online Access: http://eprints.sunway.edu.my/712/1/Tiekink%20A%20multicomponent%20RSC%20Adv%202017%20.pdf; http://eprints.sunway.edu.my/712/

An efficient and highly selective multicomponent synthesis of 4-aminoimidazo[1,2-a][1,3,5]triazines, which are 5-aza-7-deaza-isosteres of adenine, was developed. The reaction of 2-aminoimidazoles, triethyl orthoformate and cyanamide under microwave irradiation proceeded regioselectively to provide a library of novel 5-aza-7-deaza-adenines in good yields and purity. The developed method was demonstrated to be scalable and highly reproducible in three different monomode microwave reactors. A rearrangement was proposed to explain the high selectivity of the reaction.