Access to novel imidazo[1,5-a]pyrazine scaffolds by the combined use of a three-component reaction and a base-assisted intramolecular cyclization?

Organic & Biomolecular Chemistry Pub Date: 2014-05-22 DOI: 10.1039/C4OB00676C

Abstract

A novel and practical two-step approach to an intriguing class of imidazo[1,5-a]pyrazines with exocyclic C[double bond, length as m-dash]X (X = CH2, O) bonds is described. The process utilizes a sequential three-component reaction of propargyl amine or aminoester, 1,2-diaza-1,3-dienes and isothiocyanates to furnish functionalized 2-thiohydantoins which are transformed into thiohydantoin-fused tetrahydropyrazines by subsequent regioselective base-promoted cyclization.

Graphical abstract: Access to novel imidazo[1,5-a]pyrazine scaffolds by the combined use of a three-component reaction and a base-assisted intramolecular cyclization
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