Issue 7, 2011
From the journal:

Organic & Biomolecular Chemistry

A new diversity oriented and metal-free approach to highly functionalized 3H-pyrimidin-4-ones

Renata Riva,*a   Luca Banfi,a   Andrea Bassoa  and  Paola Zitoa  

* Corresponding authors

a Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso 31, 16146 Genova, Italy
E-mail: riva@chimica.unige.it
Fax: +39 010 3536118
Tel: +39 010 3536106

Abstract

A new synthesis of 3H-pyrimidin-4-ones, characterized by four different sets of decorations, is presented. The strategy is based on the synthetic elaboration of readily available α-substituted β-ketoesters that, upon transformation into the corresponding acyl enamines, have been cyclized to give 6H-1,3-oxazin-6-ones. These reactive intermediates have been in turn cleanly converted into highly functionalized pyirimidinones, by treatment with an appropriate primary amine. The whole sequence does not need the use of any metal mediator or catalyst.

Graphical abstract: A new diversity oriented and metal-free approach to highly functionalized 3H-pyrimidin-4-ones

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DOI
https://doi.org/10.1039/C0OB00978D
Article type
Paper
Submitted
03 Nov 2010
Accepted
13 Dec 2010
First published
13 Jan 2011

Org. Biomol. Chem., 2011,9, 2107-2122

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A new diversity oriented and metal-free approach to highly functionalized 3H-pyrimidin-4-ones

R. Riva, L. Banfi, A. Basso and P. Zito, Org. Biomol. Chem., 2011, 9, 2107 DOI: 10.1039/C0OB00978D

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