Issue 81, 2017, Issue in Progress

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
13 Oct 2017
Accepted
30 Oct 2017
First published
02 Nov 2017
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2017,7, 51062-51068

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

F. P. L. Lim, S. T. Low, E. L. K. Ho, N. R. Halcovitch, E. R. T. Tiekink and A. V. Dolzhenko, RSC Adv., 2017, 7, 51062 DOI: 10.1039/C7RA11305F

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