An Efficient Synthetic Approach to Substituted Trisphenols (Phloroglucide Analogues) Using Tungstosilicic Acid in Water

Reza Fareghi-Alamdari; Ali Khalafi-Nezhad; Negar Zekri

doi:10.1055/s-0033-1340681

Synthesis, Table of Contents

Synthesis 2014; 46(07): 887-892
DOI: 10.1055/s-0033-1340681

paper

An Efficient Synthetic Approach to Substituted Trisphenols (Phloroglucide Analogues) Using Tungstosilicic Acid in Water

Reza Fareghi-Alamdari*

^aFaculty of Chemistry & Chemical Engineering, Malek-Ashtar University of Technology, Tehran, Iran Fax: +98(21)22970195 Email: reza_fareghi@yahoo.com

,

Ali Khalafi-Nezhad

^bCollege of Science, Department of Chemistry, Shiraz University, Shiraz, Iran

,

Negar Zekri

^aFaculty of Chemistry & Chemical Engineering, Malek-Ashtar University of Technology, Tehran, Iran Fax: +98(21)22970195 Email: reza_fareghi@yahoo.com

› Author Affiliations

Abstract

All articles of this category

Abstract

Tungstosilicic acid was found to be an efficient catalyst for the synthesis of trisphenols using the reaction of 2,6-bis(hydroxymethyl)phenols with phenols in an aqueous medium. The catalytic reactivity of tungstosilicic acid in boiling water was examined with a series of substrates, demonstrating that this catalyst is reactive in the presence of a variety of functionalities.

Key words

tungstosilicic acid - trisphenols - phenols - 2,6-bis(hydroxymethyl)phenols - synthesis

Full Text

References

References

1a Stockley C, Teissedre PL, Boban M, Lorenzo CD, Restani P. Food Funct. 2012; 3: 995
1b Mesganaw T, Garg NK. Org. Process Res. Dev. 2013; 17: 29
1c Guo YJ, Deng GF, Xu XR, Wu S, Li S, Xia EQ, Li F, Chen F, Ling WH, Li HB. Food Funct. 2012; 3: 1195
1d Hasegawa I, Nakamura T, Motojima S, Kajiwara M. J. Mater. Chem. 1995; 5: 193

2a Weinger JS, Strobel SA. Biochemistry 2006; 45: 5939
2b He K, Shi G, Zhao GX, Zeng L, Ye Q, Schwedler JT, Wood KV, McLaughlin JL. J. Nat. Prod. 1996; 59: 1029
2c Parker SF. Chem. Commun. 2011; 47: 1988
2d Niu F, Liu CC, Cui ZM, Zhai J, Jiang L, Song WG. Chem. Commun. 2008; 2803

3a Huang H, Sun HD, Wang MS, Zhao SX. J. Nat. Prod. 1996; 59: 1079
3b Song MC, Nigussie F, Jeong TS, Lee CY, Regassa F, Markos T, Baek NI. J. Nat. Prod. 2006; 69: 853
3c Nomura T, Hano Y. Nat. Prod. Rep. 1994; 11: 205
3d Whiting DA. Nat. Prod. Rep. 2001; 18: 583

4a Money T. Chem. Rev. 1970; 70: 553
4b Kametani T, Fukumoto K, Yagi H, Satoh F. Chem. Commun. 1967; 878

5a Widén C.-J, Fraser-Jenkins CR, Lounasmaa M, Euw J.v, Reichstein T. Helv. Chim. Acta 1973; 56: 831
5b Appendino G, Ottino M, Marquez N, Bianchi F, Giana A, Ballero M, Sterner O, Fiebich BL, Munoz E. J. Nat. Prod. 2007; 70: 608
5c Closse A, Sigg HP. Helv. Chim. Acta 1973; 56: 619
5d Albert A. Nature 1953; 172: 201
5e Fu GM, Yu BY, Zhu DN. J. Asian Nat. Prod. Res. 2006; 8: 149
5f Hakimelahi GH, Moshfegh AA. Helv. Chim. Acta 1981; 64: 599
5g Moshfegh AA, Mazandarani B, Nahid A, Hakimelahi GH. Helv. Chim. Acta 1982; 65: 1229

6a Böhmer V, Marschollek F, Zetta L. J. Org. Chem. 1987; 52: 3200
6b Kraft D, Cacciapaglia R, Böhmer V, El-Fadl AA, Harkema S, Mandolini L, Reinhoudt DN, Verboom W, Vogt W. J. Org. Chem. 1992; 57: 826

7 Sharma K, Cragg PJ. Chem. Sens. 2011; 1: 1

8a Gutsche CD. Calixarenes: An Introduction . 2nd ed. RSC Publishing; Cambridge: 2008
8b Calixarenes . Asfari Z, Böhmer V, Harrowfield J, Vicens J, Saadioui M. Kluwer Academic Publishers; Dordrecht: 2001

9a Böhmer V, Chhim P, Kammerer H. Makromol. Chem. 1979; 180: 2503
9b Böhmer V, Merkel L, Kunz U. J. Chem. Soc., Chem. Commun. 1987; 896
9c Böhmer V, Vogt W. Pure Appl. Chem. 1993; 65: 403
9d Pappalardo S, Ferguson G, Gallagher JF. J. Org. Chem. 1992; 57: 7102
9e Grüttner C, Böhmer V, Vogt W, Thondorf I, Biali SE, Grynszpan F. Tetrahedron Lett. 1994; 35: 6267

10 Gopalsamuthiram V, Wulff WD. J. Am. Chem. Soc. 2004; 126: 13936
11 Rodia JS. J. Org. Chem. 1961; 26: 2966
12 Khalafi-Nezhad A, Soltani Rad MN, Hakimelahi GH. Helv. Chim. Acta 2003; 86: 2396
13 Khalafi-Nezhad A, Parhami A, Bargebid R, Molazade S, Zare A, Foroughi H. Mol. Diversity 2011; 15: 373
14 Foster HM, Hein DW. J. Org. Chem. 1961; 26: 2539

15a Fareghi-Alamdari R, Hosseinabadi Z, Farhadi-Khouzani M. J. Chem. Sci. 2012; 124: 827
15b Fareghi-Alamdari R, Golestanzadeh M, Agend F, Zekri N. C. R. Chim. 2013; 16: 878
15c Fareghi-Alamdari R, Golestanzadeh M, Agend F, Zekri N. J. Chem. Sci. 2013; 125: 1185
15d Fareghi-Alamdari R, Golestanzadeh M, Agend F, Zekri N. Can. J. Chem. 2013; 91: 982

16 McGarry EJ, Forsyth BA. US Patent 4282390, 1981
17 Sharghi H, Jokar M. Synth. Commun. 2009; 39: 958
18 Firouzabadi H, Jafari AA. J. Iran. Chem. Soc. 2005; 2: 85
19 Heydari A, Khaksar S, Sheykhan M, Tajbakhsh M. J. Mol. Catal. A: Chem. 2008; 287: 5

20a Yang L, Xu LW, Xia CG. Tetrahedron Lett. 2008; 49: 2882
20b Timofeeva MN. Appl. Catal., A 2003; 256: 19

21 Forsyth BA, McGarry EJ. US Patent 4163801, 1979

Supplementary Material

Supporting Information