Preyssler Heteropoly Acids Encapsulated in a Silica Framework for an ­Efficient Preparation of Fluorinated Hexahydropyrimidine Derivatives under Solvent-Free Conditions

Ángel G. Sathicq; Diego M. Ruiz; Tierry Constantieux; Jean Rodriguez; Gustavo P. Romanelli

doi:10.1055/s-0033-1340845

Synlett, Table of Contents

Synlett 2014; 25(6): 881-883
DOI: 10.1055/s-0033-1340845

letter

Preyssler Heteropoly Acids Encapsulated in a Silica Framework for an Efficient Preparation of Fluorinated Hexahydropyrimidine Derivatives under Solvent-Free Conditions

Ángel G. Sathicq*

^aCentro de Investigación y Desarrollo en Ciencias Aplicadas ‘Dr. Jorge J. Ronco’ (CINDECA-CCT-CONICET), Universidad Nacional de La Plata, Calle 47 No. 257, B1900AJK La Plata, Argentina Email: agsathicq@quimica.unlp.edu.ar Email: gpr@quimica.unlp.edu.ar Fax: +54(221)4211353125

,

Diego M. Ruiz

^bCátedra de Química Orgánica, Facultad de Ciencias Agrarias y Forestales, Universidad Nacional de La Plata, Calles 60 y 119 s/n, B1904AAN La Plata, Argentina

,

Tierry Constantieux

^cInstitut des Sciences Moléculaires de Marseille-UMR CNRS 7313 iSm2, Aix-Marseille Université Centre Saint Jérôme, Service 531, 13397 Marseille Cedex 20, France

,

Jean Rodriguez

^cInstitut des Sciences Moléculaires de Marseille-UMR CNRS 7313 iSm2, Aix-Marseille Université Centre Saint Jérôme, Service 531, 13397 Marseille Cedex 20, France

,

Gustavo P. Romanelli*

^aCentro de Investigación y Desarrollo en Ciencias Aplicadas ‘Dr. Jorge J. Ronco’ (CINDECA-CCT-CONICET), Universidad Nacional de La Plata, Calle 47 No. 257, B1900AJK La Plata, Argentina Email: agsathicq@quimica.unlp.edu.ar Email: gpr@quimica.unlp.edu.ar Fax: +54(221)4211353125

^bCátedra de Química Orgánica, Facultad de Ciencias Agrarias y Forestales, Universidad Nacional de La Plata, Calles 60 y 119 s/n, B1904AAN La Plata, Argentina

› Author Affiliations

Abstract

All articles of this category

Abstract

A series of trifluoromethylated hexahydropyrimidines was synthesized using Preyssler heteropoly acid H₁₄NaP₅W₂₉MoO₁₁₀ encapsulated in a silica framework as the catalyst under solvent-free conditions. This synthesis requires short reaction times (1.5 h) and 80 °C under solvent-free conditions to obtain good to excellent yields of 18 hexahydropyrimidine derivatives. Preyssler catalyst embedded in the silica matrix, unlike the bulk or supported on silica, is insoluble in polar media such as acetone, ethanol, or methanol, which allows easy removal of the reaction products without affecting catalytic activity.

Key words

fluorinated hexahydropyrimidines - trifluoromethyl derivatives - Preyssler heteropoly acid - encapsulated in a silica framework - solvent-free - multicomponent reactions

Full Text

References

References

1a Beletskaya I, Tyurin V. Molecules 2010; 15: 4792
1b Corma A, Garcia H. Adv. Synth. Catal. 2006; 348: 1391
1c Sheldon RA. Chem. Soc. Rev. 2012; 41: 1437
1d Datan A, Kulkarni A, Torok B. Green Chem. 2012; 14: 17
1e Su D, Zhang J, Frank B, Thomas A, Wang X, Paraknowitsch J, Schlog R. ChemSusChem 2010; 3: 169

2a Watson W. Green Chem. 2012; 14: 251
2b Kalidindi S, Jagirdar B. ChemSusChem 2012; 5: 65
2c Mulvihill M, Beach M, Zimmerman E, Anastas P. Annu. Rev. Environ. Res. 2011; 36: 271

3a Singh M, Chowdhury S. RSC Adv. 2012; 2: 4547
3b Shearouse W, Waddell D, Mack J. Curr. Opin. Drug Discov. Dev. 2009; 12: 772
3c Kalita P, Kumar R. Microporous Mesoporous Mat. 2012; 149: 1

4 Niknam K, Saberi D, Mohagheghnejad M. Molecules 2009; 14: 1915

5a Timofeeva MN. Appl. Catal., A 2003; 256: 19
5b Romanelli G, Autino J. Mini-Rev. Org. Chem. 2009; 6: 359

6 Ruiz D, Autino J, Quaranta N, Vázquez P, Romanelli G. Sci. World J. 2012; 174784
7 Bennardi D, Ruiz D, Romanelli G, Baronetti G, Thomas H, Autino J. Lett. Org. Chem. 2009; 5: 607

8a Pasquale G, Ruiz D, Autino J, Baronetti G, Thomas G, Romanelli G. C. R. Chim. 2012; 15: 758
8b Romanelli G, Ruiz D, Autino J, Giaccio H. Mol. Diversity 2010; 15: 803

9a Liéby-Muller F, Constantieux T, Rodriguez J. J. Am. Chem. Soc. 2005; 127: 17176
9b Isambert N, Duque M, Plaquevent J, Génisson Y, Rodriguez J, Constantieux T. Chem. Soc. Rev. 2011; 40: 1347

10a Kappe CO, Falsone SF, Fabian WM. F, Belaj F. Heterocycles 1999; 51: 77
10b Saloutin V, Burgart Y, Kuzueva O, Kappe CO, Chupakhin O. J. Fluorine Chem. 2000; 103: 17

11 Agbaje O, Fadeyi O, Fadeyi S, Myles L, Okoro C. Bioorg. Med. Chem. Lett. 2011; 21: 989
12 Ryabukhin S, Plaskon A, Ostapchuk E, Volochyuk D, Shishkin O, Tolmachev A. J. Fluorine Chem. 2008; 129: 625
13 Zohdi H, Rateb N, Elnagdy S. Eur. J. Med. Chem. 2011; 46: 5636
14 Li G, Wu C, Guo L, Yang F. Acta Crystallogr., Sect. E: Struct. Rep. Online 2011; 67: 704
15 Bose D, Sudharshan M, Chavhan S. ARKIVOC 2005; (iii): 228
16 Reddy C, Mahesh M, Raju P, Babu T, Reddy V. Tetrahedron Lett. 2002; 43: 2657
17 Pasquale G, Vázquez P, Romanelli G, Baronetti G. Catal. Commun. 2012; 18: 115

Supplementary Material

Supporting Information

Preyssler Heteropoly Acids Encapsulated in a Silica Framework for an ­Efficient Preparation of Fluorinated Hexahydropyrimidine Derivatives under Solvent-Free Conditions

Preyssler Heteropoly Acids Encapsulated in a Silica Framework for an Efficient Preparation of Fluorinated Hexahydropyrimidine Derivatives under Solvent-Free Conditions