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

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  • Felicia Phei Lin Lim
  • Szy Teng Low
  • Elvina Lee King Ho
  • Nathan R. Halcovitch
  • Edward R. T. Tiekink
  • Anton V. Dolzhenko
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<mark>Journal publication date</mark>2017
<mark>Journal</mark>RSC Advances
Issue number81
Volume7
Number of pages7
Pages (from-to)51062-51068
Publication StatusPublished
Early online date2/11/17
<mark>Original language</mark>English

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.