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Issue 26, 2014
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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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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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Article information


Submitted
31 Mar 2014
Accepted
29 Apr 2014
First published
22 May 2014

Org. Biomol. Chem., 2014,12, 4610-4619
Article type
Paper
Author version available

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

O. A. Attanasi, G. Favi, G. Giorgi, R. Majer, F. R. Perrulli and S. Santeusanio, Org. Biomol. Chem., 2014, 12, 4610
DOI: 10.1039/C4OB00676C

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