Silica sulfuric acid as mild and efficient catalyst for the preparation of poly-hydroxyl aromatic compounds under mild and heterogeneous conditions

Molecular Diversity

Volumn 15, Issue 2, 2011, Pages 373-381

  Khalafi Nezhad, Ali ^a   Parhami, Abolfath ^a,b   Bargebid, Rahele ^a   Molazade, Saghar ^a   Zare, Abdolkarim ^a,b   Foroughi, Habib ^a  

^a SHIRAZ UNIVERSITY   (Iran)

^b PAYAME NOOR UNIVERSITY   (Iran)

Author keywords

Alkylation; Heterogeneous; Phloroglucides; Poly hydroxyl aromatic compounds; Silica sulfuric acid

Indexed keywords

2,2' (2 HYDROXY 5 METHYL 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 CHLOROPHENOL); 2,2' (2 HYDROXY 5 METHYL 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 METHYLPHENOL); 2,2' (2 HYDROXY 5 METHYL 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 OCTYLPHENOL); 2,2' (2 HYDROXY 5 METHYL 1,3 PHENYLENE)BIS(METHYLENE)DIBENZENE 1,3,5 TRIOL; 2,2' (2 HYDROXY 5 NITRO 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 CHLOROPHENOL); 2,2' (5 BROMO 2 HYDROXY 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 BROMOPHENOL); 2,2' (5 BROMO 2 HYDROXY 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 CHLOROPHENOL); 2,2' (5 BROMO 2 HYDROXY 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 FLUOROPHENOL); 2,2' (5 BROMO 2 HYDROXY 1,3 PHENYLENE)BIS(METHYLENE)DIBIPHENYL 4 OL; 2,2' (5 CHLORO 2 HYDROXY 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 BROMOPHENOL); 2,2' (5 CHLORO 2 HYDROXY 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 CHLOROPHENOL); 2,2' (5 CHLORO 2 HYDROXY 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 FLUOROPHENOL); 2,2' (5 CHLORO 2 HYDROXY 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 IODOPHENOL); 2,2' (5 CHLORO 2 HYDROXY 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 METHOXYPHENOL); 2,2' (5 CHLORO 2 HYDROXY 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 METHYLPHENOL); 2,2' (5 CHLORO 2 HYDROXY 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 NITROPHENOL); 2,2' (5 CHLORO 2 HYDROXY 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 TERT BUTYLPHENOL); 2,2' (5 CHLORO 2 HYDROXY 1,3 PHENYLENE)BIS(METHYLENE)DIBENZENE 1,4 DIOL; 3,3' (5 CHLORO 2 HYDROXY 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 HYDROXYBENZALDEHYDE); 3,3' (5 CHLORO 2 HYDROXY 1,3 PHENYLENE)BIS(METHYLENE)DIBIPHENYL 4 OL; 4,4' (2 HYDROXY 5 METHYL 1,3 PHENYLENE)BIS(METHYLENE)DIBENZENE 1,2,3 TRIOL; 4,4' (2 HYDROXY 5 METHYL 1,3 PHENYLENE)BIS(METHYLENE)DIBENZENE 1,3 DIOL; 6,6' (5 BROMO 2 HYDROXY 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 ALLYL 2 METHOXYPHENOL); 6,6' (5 CHLORO 2 HYDROXY 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 ALLYL 2 METHOXYPHENOL); 6,6' (5 CHLORO 2 HYDROXY 1,3 PHENYLENE)BIS(METHYLENE)BIS(4 CHLORO 3 METHYLPHENOL); AROMATIC COMPOUND; HYDROXYL GROUP; SILICA SULFURIC ACID; SULFURIC ACID; UNCLASSIFIED DRUG; AROMATIC HYDROCARBON; DRUG; HYDROXIDE; PHENOL DERIVATIVE; SILICATE; SOLVENT;

ARTICLE; CATALYST; DRUG SYNTHESIS; PRIORITY JOURNAL; PURIFICATION; CATALYSIS; CHEMISTRY; DRUG DEVELOPMENT; DRUG EFFECT; METABOLISM; SYNTHESIS;

CATALYSIS; DRUG DISCOVERY; HYDROCARBONS, AROMATIC; HYDROXIDES; PHARMACEUTICAL PREPARATIONS; PHENOLS; SILICATES; SOLVENTS; SULFURIC ACIDS;

EID: 80051573782     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-011-9303-8     Document Type: Article

References (26)

1. Widen CJ, Fraser-Jenkins CR, Lounasmaa M, Eaw JV, Reichstein T (1971) Die phloroglucide von dryopteris caucasica (A. Br.). Helv Chim Acta 56:831-838. doi:10.1002/hlca. 19730560304
2. Appendino G, Ottino M, Marquez N, Bianchi F, Giana A, Ballero M, Sterner O, Fiebich BL, Munoz E (2007) Arzanol, an anti-inflammatory and anti-HIV-1 phloroglucinol α-pyrone from Helichrysum italicum ssp. microphyllum. J Nat Prod 70:608-612. doi:10.1021/np060581r (Pubitemid 46797865)
3. Closse A, Sigg H-P (1973) Isolierung und strukturaufklarüng von cryptosporin. Helv Chim Acta 56:619-625. doi:10.1002/hlca. 19730560207
4. Albert A (1953) Avidity of terramycin and aureomycin for metallic cations. Nature 172:201. doi:10.1038/172201a0
5. Fu GM, Yu BY, Zhu DN (2006) Two novel phloroglucinol derivatives from Euphorbia ebracteolata hayata. J Asian Nat Prod Res 8:149-153. doi:10.1080/1028602042000325663 (Pubitemid 43879877)
6. McGarry EJ, Forsyth BA (1981) 2, 6-Benzyl substituted phenols. U. S. Patent 4282390
7. Hakimelahi GH, Moshfegh AA (1981) The synthesis of polyfunctional aromatic ring systems. Structural analogues of phloroglucides, aranciamycin, cryptosporin andterramycin. Helv Chim Acta 64:599-609. doi: 10.1002/hlca. 19810640224
8. Moshfegh AA, Mazandarani B, Nahid A, Hakimelahi GH (1982) The synthesis of hetero-halogenated derivatives of phloroglucide analogues. Helv Chim Acta 65:1229-1232. doi: 10.1002/hlca. 19820650412
9. Moshfegh AA, Badri R, Hojjatie M, Kaviani M, Naderi B, Nazmi AH, Ramezanian M, Roozpeikar B, Hakimelahi GH (1982) The synthesis of 4, 11, 18, 25-tetrachloro[14] metacyclophane-7, 14, 21, 28-tetrol. Structural analogues of phloroglucides. Helv Chim Acta 65:1221-1228. doi:10.1002/hlca.19820650411
10. Hwu JR, Tsay S-C, Hakimelahi GH, Lin CC, Tseng WN, Moshfegh AA, Azaripour A, Mottaghian H (2001) Phloroglucidic acid and derivatives as antibacterial agents. U. S. Patent 6288265 B1
11. Hwu JR, Moshfegh AA, Tsay S-C, Lin CC, Tseng WN, Azaripour A, Mottaghian H, Hakimelahi GH (1997) Cephalosporin 3'-phloroglucide esters and (phloroglucidamido) cephalosporins as novel antibacterial agents. J Med Chem 40:3434-3441. doi:10.1021/jm960810e (Pubitemid 27441335)
12. Castillo GM, Choi PY, Snow AD (2007) Polyhydroxylated aromatic compounds for the treatment of amyloidosis and alphasynuclein fibril formation. U. S. Patent 2007/0191330 A1
13. Shaw J, Urgaonkar S, Ray-Chaudhuri D, La Pierre H (2007) Synthesis of inhibitors of FtsZ. W. O. Patent 2007/056188
14. Böhmer V, Marschollek F, Zetta L (1987) Calix[4]arenes withfour differently substituted phenolic units. J Org Chem 52:3200-3205. doi:10.1021/jo00391a005
15. Kraft D, Cacciapaglia R, Böhmer V, El-Fadl AA, Harkema S, Mandolini L, Reinhoudt DN, Verboom W, Vogt W (1992) New crown ether-like macrocycles containing a nitrophenol unit. Synthesis and metal ion effects on the reactivity of their acetates in transacylation reactions. J Org Chem 57:826-834. doi: 10.1021/jo00029a009
16. Saitoh A, Osato Y, Kazunori U (2006) Organic luminescence device. U. S. Patent 6998182 B2
17. Durairaj RB (2005) Resorcinol: chemistry, technology and applications, In: Resorcinol chemistry in photoresist technology. Springer-Verlag, Berlin Heidelberg, pp 717-732, ISBN-10 3-540-25142-1, doi:1007/b982897
18. Khalafi-Nezhad A, Soltani Rad MN, Hakimelahi GH (2003) Synthesis of polyfunctional aromatic ring systems (phloroglucide analogs) under microwave irradiation. Helv Chim Acta 86:2396-2403. doi: 10.1002/hlca.200390192 (Pubitemid 37011959)
19. Rodia JS (1961) Self catalysis by certain phenols in the synthesis of di-and trinuclear novolacs. J Org Chem 26:2966-2969. doi: 1021/jo01066a082
20. Sheldon RA, Bekkum HV (2001) Fine chemicals through heterogeneous catalysis, 1st Ed, Wiley-VCH, ISBN-10:3527299513
21. Salehi P, Zolfigol MA, Shirini F, Baghbanzadeh M (2006) Silica sulfuric acid and silica chloride as efficient reagents for organic reactions. Curr Org Chem 10:1-19. doi: 10.2174/138527206778742650 (Pubitemid 44669764)
22. 2 as a novel heterogeneous system for the coupling of thiols to their corresponding disulfides. Phosphorus Sulfur 179:2177-2182. doi:10.1080/10426500490474842 (Pubitemid 39586077)
23. Prager RH, Yurui Z (1989) Preparation of carboxylate esters of polyhydric alcohols by using a sulfonated charcoal catalyst. Aust J Chem 42:1003-1005. doi:10.1071/CH9891003
24. 3H: a novel and recyclable catalyst for one-pot synthesis of 3, 4- dihydropyrimidinones or their sulfur derivatives in biginelli condensation. Synth Commun 39:958-979. doi:10.1080/00397910802444258
25. Foster HM, Hein DW (1961) Phenol-formaldehyde condensations. J Org Chem 26:2539-2541. doi:10.1021/jo01351a609 26.
26. Kämmerer H, Eberle K, Böhmer V, Großmann M (1975) Darstellung und spektroskopische analyse von oligo{[4-(-(1, 1, 3, 3-tetramethylbutyl) (bzw. 4-octyl)-2-hydroxy-1, 3-phenylen]methylen}en und ihrer ausgangsverbindungen. Macromol Chem 176:3295-3315. doi:10.1002/macp. 1975.021761114