4-Unsubstituted, 5-Amino and 5-Unsubstituted, 4-Aminoimidazoles

Add time:08/13/2019    Source:sciencedirect.com

Publisher SummaryThis chapter deals with the chemistry of 4 and 5-aminoimidazoles, the compounds of recently recognized biological importance. In most living systems, 5-amino-1-(β-D-ribofuranosyl)-imidazole-5’-monophosphate (AIR) is an intermediate in the de novo biosynthesis of purine ribonucleotides. It is also used as a biosynthetic precursor of thiamin in some lower organisms. This important aminoimidazole derivative is also used as a synthetic intermediate for the chemistry of simple 5-aminoimidazoles and the isomeric 4-aminoimidazoles. The stabilities and reactivities of monoaminoazoles vary considerably, and are related to the number of nitrogen atoms in the heterocyclic ring. Nitrogen atoms stabilize dipolar canonical forms that contribute significantly to the electronic structure. The chapter also describes the physical properties and theoretical studies of aminoimidazoles that includes studies concerning spectroscopic methods, 13C and I5N NMR spectroscopy, ultraviolet spectroscopy, and infrared and mass spectroscopy. The chapter considers the imidazoles with the absence of a substituent on the ring carbon atom adjacent to the amino substituent.

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