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A route to functionalized pyrimidines from carbohydrates via amine-driven dehydrative ring transformations

✍ Scribed by Lal Dhar S. Yadav; Chhama Awasthi; Vijai K. Rai; Ankita Rai

Book ID: 104095097
Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 122 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.02.067

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✦ Synopsis

A novel and expeditious synthetic protocol for functionalized pyrimidines using unprotected aldoses as biorenewable resources is reported. The synthesis involves aza-Michael addition of aromatic amines to aldose-derived 1,3-oxazin-2-ones(thiones) followed by dehydrative ring transformation to afford 4-polyhydroxyalkylpyrimidin-2-ones(thiones) in excellent yields. This is a one-pot Montmorillonite K-10 clay-catalyzed amine-driven process proceeding under solvent-free microwave irradiation conditions.

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