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Synthesis 2018; 50(10): 2087-2093
DOI: 10.1055/s-0037-1609364
DOI: 10.1055/s-0037-1609364
paper
A Convenient and Concise Metal-Free Approach to Functionalized Bicyclic Pyrimidinones from Oxazine-2,6-diones
Authors
We thank Syngenta Research & Technology Centre, Goa for providing the research facility and thank the management for supporting this work.
Further Information
Publication History
Received: 31 January 2018
Accepted after revision: 22 February 2018
Publication Date:
20 March 2018 (online)
Abstract
The synthesis of previously unreported pyrazolo-pyrimidinones and isoxazolo-pyrimidinones are achieved via metal-free coupling of oxazine-2,6-diones with pyrazolidinone and isoxazolidinone, respectively. The synthesis provides easy access to a variety of novel 2-dimensional building blocks that can be derivatized to generate a range of drug- and agro-like molecules.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609364.
- Supporting Information (PDF)
- CIF File (ZIP)
-
References
- 1a Cagir A. Jones SH. Gao R. Eisenhauer BM. J. Am. Chem. Soc. 2003; 125: 13628
- 1b Tseng M.-C. Chu Y.-W. Tsai H.-P. Lin C.-M. Hwang J. Chu Y.-H. Org. Lett. 2011; 13: 920
- 1c Servais A. Azzouz M. Lopes D. Courillon C. Malacria M. Angew. Chem. Int. Ed. 2007; 46: 576
- 2 Kumar KS. Kumar PM. Rao VS. Jafar AA. Meda CL. T. Kapavarapu R. Parsac KV. L. Pal M. Org. Biomol. Chem. 2012; 10: 3098
- 3 Giornal F. Pazenok S. Rodefeld L. Lui N. Vors J. Leroux FR. J. Fluorine Chem. 2013; 152: 2
- 4a Qiao R. Ye L. Hu K. Yu S. Yang W. Liu M. Chen J. Ding J. Wu H. Org. Biomol. Chem. 2017; 15: 2168
- 4b Chen D. Dou G. Li Y. Liu Y. Wang X. J. Org. Chem. 2013; 78: 5700
- 4c Yang W. Ye L. Huang D. Liu M. Ding J. Chen J. Wu H. Tetrahedron 2013; 69: 9852
- 4d Yang W. Chen J. Huang X. Ding J. Liu M. Wu H. Org. Lett. 2014; 16: 5418
- 4e Yang W. Qiao R. Chen J. Huang X. Liu M. Gao W. Ding J. Wu H. J. Org. Chem. 2015; 80: 482
- 5 Dunn AD. Kinnear KI. Norrie R. Ringan N. Martin D. J. Heterocycl. Chem. 1987; 24: 175
- 6 Beccalli EM. Marchesini A. Molinari H. Tetrahedron Lett. 1986; 27: 627
- 7 Beccalli EM. Marchesini A. J. Org. Chem. 1987; 52: 3426
- 8 Gould E. Lebl T. Slawin AM. Z. Reid M. Smith AD. Tetrahedron 2010; 66: 8992
- 9 Bobek M. Kuhar S. Bloch A. J. Med. Chem. 1979; 22: 592
- 10 CCDC 1818542 (23) and 1818638 (35) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.