A novel and practical two-step approach to an intriguing class of imidazo[1,5-a]pyrazines with exocyclic C=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.
Attanasi, O.A., Favi, G., Giorgi, G., Majer, R., Perrulli, F.R., Santeusanio, S. (2014). 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, 12(26), 4610-4619 [10.1039/c4ob00676c].
Access to novel imidazo[1,5-a]pyrazine scaffolds by the combined use of a three-component reaction and a base-assisted intramolecular cyclization
Giorgi G.;
2014-01-01
Abstract
A novel and practical two-step approach to an intriguing class of imidazo[1,5-a]pyrazines with exocyclic C=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.
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https://hdl.handle.net/11365/48558
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