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

Lim, Felicia Phei Lin and Low, Szy Teng and Ho, Elvina Lee King and Halcovitch, Nathan R. and Tiekink, Edward R. T. * and Dolzhenko, Anton V (2017) A multicomponent reaction of 2-aminoimidazoles: microwave-assisted synthesis of novel 5-aza-7- deaza-adenines†‡. RSC Advances, 7 (81). pp. 51062-51068. ISSN 2046-2069

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Abstract

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.

Item Type: Article
Subjects: Q Science > QD Chemistry
Divisions: Others > Non Sunway Academics
Depositing User: Dr Janaki Sinnasamy
Date Deposited: 21 Dec 2017 08:43
Last Modified: 14 Feb 2018 01:44
URI: http://eprints.sunway.edu.my/id/eprint/712

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