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. 2022 May 7;27(9):3013.
doi: 10.3390/molecules27093013.

Simple and Expedient Access to Novel Fluorinated Thiazolo- and Oxazolo[3,2- a]pyrimidin-7-one Derivatives and Their Functionalization via Palladium-Catalyzed Reactions

Wafa Blancou  1   2 , Badr Jismy  1 , Soufiane Touil  2 , Hassan Allouchi  3 , Mohamed Abarbri  1
Affiliations

Simple and Expedient Access to Novel Fluorinated Thiazolo- and Oxazolo[3,2- a]pyrimidin-7-one Derivatives and Their Functionalization via Palladium-Catalyzed Reactions

Wafa Blancou et al. Molecules. .

Abstract

An efficient, versatile, and one-pot method for the preparation of novel fluorinated thiazolo- and oxazolo[3,2-a]pyrimidin-7-ones is described from 2-aminothiazoles or 2-amino-oxazoles and fluorinated alkynoates. This transformation, performed under transition-metal-free conditions, offers new fluorinated cyclized products with good to excellent yields. Moreover, the functionalization of these N-fused scaffolds via the Suzuki-Miyaura and Sonogashira cross-coupling reactions led to the synthesis of highly diverse thiazolo- and oxazolo[3,2-a]pyrimidin-7-ones.

Keywords: Sonogashira coupling; Suzuki-Miyaura; fluorinated alkynes; one-pot reaction; oxazolo[3,2-a]pyrimidin-7-ones; regioselective; thiazolo[3,2-a]pyrimidin-7-ones.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Examples of thiazolo- and oxazolo[3,2-a]pyrimidinone structural analogues used in clinical medicine.
Figure 2
Figure 2
Convergent approach for the synthesis of thiazolo- and oxazolo[3,2-a]pyrimidinone derivatives. (a) from symmetric alkyne[28,29,30,31,32,33,34,35,36]; (b) from asymmetric alkyne [37,38,39,40]; (c) extension to fluorinated ethyl propiolate derivatives.
Figure 3
Figure 3
X-ray single-crystal structure of compound 3a.
Scheme 1
Scheme 1
Substrate scope studies.
Scheme 2
Scheme 2
Behavior of 2-bromo-5-fluoroalkylthiazolo[3,2-a]pyrimidin-7-ones in the Suzuki-Miyaura coupling.
Scheme 3
Scheme 3
Behavior of 2-bromo-5-(trifluoromethyl)thiazolo[3,2-a]pyrimidin-7-one 3e in the Sonogashira coupling.
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References

    1. Sawant R.L., Ramdin S.S., Wadekar J.B. Synthesis, QSAR and docking studies of 5HT2A receptor antagonising thiazolo[3,2-a]pyrimidines as antipsychotic agents. Marmara Pharm. J. 2014;18:109–119. doi: 10.12991/mpj.2014187237. - DOI
    1. Hassan G.S., El-Messery S.M., Abbas A. Synthesis and anticancer activity of new thiazolo[3,2-a]pyrimidines: DNA binding and molecular modeling study. Bioorg. Chem. 2017;74:41–52. doi: 10.1016/j.bioorg.2017.07.008. - DOI - PubMed
    1. Selvam T.P., Karthick V., Kumar P.V., Ali M.A. Synthesis and structure-activity relationship study of 2-(substituted benzylidene)-7-(4-fluorophenyl)-5-(furan-2-yl)-2H-thiazolo[3,2-a]pyrimidin-3(7H)-one derivatives as anticancer agents. Drug Discov. Ther. 2012;6:198–204. doi: 10.5582/ddt.2012.v6.4.198. - DOI - PubMed
    1. Tozkoparan B., Ertan M., Kelicen P., Demirdamar R. Synthesis and anti-inflammatory activities of some thiazolo[3,2-a]pyrimidine derivatives. Il Farmaco. 1999;54:588–593. doi: 10.1016/S0014-827X(99)00068-3. - DOI - PubMed
    1. Tozkoparan B., Ertan M., Krebs B., Läge M., Kelicen P., Demirdamar R. Condensed Heterocyclic Compounds: Synthesis and Antiinflammatory Activity of Novel Thiazolo[3,2-a]pyrimidines. Arch. Pharm. Pharm. Med. Chem. 1998;331:201–206. doi: 10.1002/(SICI)1521-4184(199806)331:6<201::AID-ARDP201>3.0.CO;2-T. - DOI - PubMed

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