Highly efficient synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes Catalyzed by carbon-based solid acid under solvent-free conditions

Synthetic Communications

Volumn 39, Issue 24, 2009, Pages 4328-4340

  Mirkhani, Valiollah ^a   Moghadam, Majid ^a   Tangestaninejad, Shahram ^a   Mohammadpoor Baltork, Iraj ^a   Mahdavi, Mohammad ^a  

^a UNIVERSITY OF ISFAHAN   (Iran)

Author keywords

Naphthol; Solid acid catalyst; Solvent free; Sulfonated carbon; Xanthene

Indexed keywords

14H DIBENZO[A,J]XANTHENE DERIVATIVE; 2 NAPHTHOL; ACID; ALDEHYDE; AROMATIC COMPOUND; CARBON; NAPHTHALENE; SULFURIC ACID; UNCLASSIFIED DRUG; XANTHENE DERIVATIVE;

ARTICLE; CARBONIZATION; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLVENT FREE METHOD; SUBSTITUTION REACTION; SULFONATION; SYNTHESIS; TECHNIQUE; TEMPERATURE;

EID: 74549216990     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902792630     Document Type: Article

References (31)

1. Singh, K.; Arora, D.; Singh, S. Heterogeneous catalyst: Amberlyst-15 catalyzes the synthesis of 14-substituted-14H-dibenzo[a,j]xanthenes under solvent-free conditions. Tetrahedron Lett. 2006, 47, 4205.
2. Kidwai, M.; Mohan, R.; Rastogi, S. Alumina-catalyzed synthesis of fused thioxopyrimidine derivatives under microwaves. Synth. Commun. 2003, 33, 3747.
3. Bacci, J. P.; Kearney, A. M.; Van Vranken, D. L. Efficient two-step synthesis of 9-aryl-6-hydroxy-3H-xanthen-3-one fluorophores. J. Org. Chem. 2005, 70, 9051.
4. Schneider, H. J.; Guttes, D.; Schneider, U. Host-guest chemistry, 15: Host-guest complexes with water-soluble macrocyclic polyphenolates including induced fit and simple elements of a proton pump. J. Am. Chem. Soc. 1988, 110, 6449.
5. Handique, J. G.; Baruah, J. B. Polyphenolic compounds: An overview. React. Funct. Polym. 2002, 52, 163.
6. Banerjee, A.; Mukherjee, A. K. Chemical aspects of santalin as a histological stain. Stain Technol. 1981, 56, 83.
7. Sirkecioglu, O.; Tulinli, N.; Akar, A. The spectroscopy and associated photo-dynamic activity of some 14-alkyl-14H-dibenzo[a,j]xanthene derivatives. J. Chem. Res. 1995, 502.
8. Knight, C. G.; Stephenes, T. Xanthene-dye-labelled phosphatidylethanol- amines as probes of interfacial pH: Studies in phospholipid vesicles. J. Bio-chem. 1989, 285, 683.
9. Hideu, T. Benzopyrano 2*33B xanthene derivative and its preparation. JP 56005480, 1981; Chem. Abstr. 1981, 95, 80923b.
10. Lamberk, R. W.; Martin, J. A.; Merrett, J. A.; Parkes, K. E. B.; Thomas, G. J. Pttrimidine nucleosides. PCT Int. Appl. WO 9706178, 1997;
11. Chem. Abstr. 1997, 126, P212377y.
12. Bhattacharya, A. K.; Rana, K. C. Microwave-assisted synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes catalysed by methanesulfonic acid under solvent-free conditions. Mendeleev Commun. 2007, 17, 247.
13. Khosropour, A. R.; Khodaei, M. M.; Moghannian, H. A simple and efficient procedure for the synthesis of amidoalkyl naphtols by P-TSA in solution or under solvent-free conditions. Synlett 2005, 916.
14. Das, B.; Ravikanth, B.; Ramu, R.; Laxminarayana, K.; Vittal Rao, B. A simple and facile synthesis of homoallylic amines using silica-supported sodium hydrogen sulfate. J. Mol. Catal. A: Chem. 2006, 253, 92.
15. Rajitha, B.; Kumar, B. S.; Reddy, Y. T.; Reddy, P. N.; Sreenivasulu, N. Sul-famic acid: A novel and efficient catalyst for the synthesis of aryl-14H-diben-zo[a,j]xanthenes under conventional heating and microwave irradiation. Tetrahedron Lett. 2005, 46, 8691.
16. Sarma, R. J.; Baruah, J. B. One step synthesis of dibenzoxanthenes. Dyes Pigm. 2005, 64, 91.
17. Shakibaei, G. I.; Mirzaei, P.; Bazgir, A. Dowex-50 W promoted synthesis of 14-aryl-14H-dibenzo[a,j]xanthene and 1,8-dioxo-octahydroxanthene derivatives under solvent-free conditions. Appl. Catal. A: Gen. 2007, 325, 188.
18. Mohammadpour Amini, M.; Seyyed Hamzeh, M.; Bazgir, A. Heteropolya-cid: An efficient and eco-friendly catalyst for the synthesis of 14-aryl-14H-dibenzo[a, j]xanthene. Appl. Catal. A: Gen. 2007, 323, 242.
19. 2 as an efficient reusable catalyst. Chin. Chem. Lett. 2008, 19, 771.
20. Bekaert, A.; Andrieus, J.; Plat, M. New total synthesis of bikaverin. Tetrahedron Lett. 1992, 33, 2805.
21. Buehler, C. A.; Cooper, D. E.; Scrudder, E. O. The stability of 2,2'-dihydroxy dipheny methane. J. Org. Chem. 1943, 8, 316.
22. Peng, F.; Zhang, L.; Wang, H.; Lv, P.; Yu, H. Sulfonated carbon nanotubes as a strong protonic acid catalyst. Carbon 2005, 43, 2397.
23. Okamura, M.; Takagaki, A.; Toda, M.; Kondo, J. N.; Domen, K.; Tatsumi, T.; Hara, M.; Hayashi, S. Acid-catalyzed reactions on flexible polycyclic aromatic carbon in amorphous carbon. Chem. Mater. 2006, 18, 3039.
24. Hara, M.; Yoshida, T.; Takagaki, A.; Takata, T.; Kondo, J. N.; Hayashi, S.; Domen, K. A carbon material as a strong protonic acid. Angew. Chem. Int. Ed. 2004, 43, 2955.
25. Anastas, P. T.; Kirchhoff, M. M. Origins, current status, and future challenges of green chemistry. Acc. Chem. Res. 2002, 35, 686.
26. Clark, J. H. Solid acids for green chemistry. Acc. Chem. Res. 2002, 35, 791.
27. Okuhara, T. Solid acid catalysts. Chem. Rev. 2002, 102, 3641.
28. Lee, J. B.; Park, Y. K.; Yong, O. B.; Kang, Y.; Jun, K. W.; Lee, Y. J.; Kim, H. Y.; Lee, K. H.; Choi, W. C. Synthesis of porous carbons having surface functional groups and their application to direct-methanol fuel cells. J. Power Sources 2006, 158, 1251.
29. Cano-Serrano, E.; Campos-Martin, J. M.; Fierro, J. L. G. Sulfonic acid-functionalized silica through quantitative oxidation of thiol groups. Chem. Commun. 2003, 246.
30. Takagaki, A.; Toda, M.; Okamura, M.; Kondo, J. N.; Hayashi, S.; Domen, K.; Hara, M. Esterification of higher fatty acids by a novel strong solid acid. Catal. Today 2006, 116, 157.
31. Zong, M. H.; Duan, Z. Q.; Lou, W. Y.; Smith, T. J.; Wua, H. Preparation of a sugar catalyst and its use for highly efficient production of biodiesel. Green Chem. 2007, 9, 434