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:
Journal Article
Journal or Publication Title:
RSC Advances
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/1600
Subjects:
ID Code:
89189
Deposited By:
Deposited On:
14 Dec 2017 09:26
Refereed?:
Yes
Published?:
Published
Last Modified:
30 Sep 2020 07:21