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

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

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...

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Bibliographic Details
Main Authors: Lim, F., Low, S., Ho, E., Halcovitch, N., Tiekink, E., Dolzhenko, Anton
Format: Journal Article
Published: Royal Society of Chemistry 2017
Online Access:http://hdl.handle.net/20.500.11937/59385
Description
Summary: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 i n three different monomode microwave reactors. A rearrangement was proposed to explain the high selectivity of the reaction.

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