Silica-supported perchloric acid (HClO4-SiO2): A versatile catalyst for tetrahydropyranylation, oxathioacetalization and thioacetalization

Synthesis

Volumn , Issue 15, 2006, Pages 2497-2502

  Khan, Abu T ^a   Parvin, Tasneem ^a   Choudhury, Lokman H ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

Alcohols; Carbonyl compounds; Oxathioacetals; Phenols; Thioacetals; THP ethers

Indexed keywords

CATALYSIS; CHLORINE COMPOUNDS; HYDROXYLATION; RATE CONSTANTS; REACTION KINETICS; SILICA;

CARBONYL COMPOUNDS; OXATHIOACETALS; THIOACETALS; THP ETHERS;

CATALYSTS;

4 NITROBENZALDEHYDE; ACETAL DERIVATIVE; ALCOHOL DERIVATIVE; BENZALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; HYDROXYL GROUP; MENTHOL; OXATHIOACETAL; PERCHLORIC ACID; PHENOL DERIVATIVE; SILICON DIOXIDE; SOLVENT; TETRAHYDROPYRANYL ETHER; THIOACETAL; UNCLASSIFIED DRUG;

ACETALIZATION; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ECONOMIC ASPECT; REACTION TIME; SYNTHESIS;

EID: 33747179606     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942465     Document Type: Article

References (50)

1. (a) González-Núñez, M. E.; Mello, R.; Olmos, A.; Asensio, G. J. Org. Chem. 2005, 70, 10879.
2. (b) Clark, J. H.; Macquarrie, D. J.; Mubofu, E. B. Green Chem. 2000, 2, 53.
3. (c) Lambert, A.; Carr, G.; Clark, J. H.; Macquarrie, D. J. New J. Chem. 2000, 24, 485.
4. (d) Hajipur, A. R.; Abidi, H.; Ruoho, A. E. J. Org. Chem. 2003, 68, 4553.
5. (e) Khadilkar, B. M.; Borkar, S. D. Tetrahedron Lett. 1997, 38, 1641.
6. Chakraborti, A. K.; Gulhane, R. Chem. Commun. 2003, 1896.
7. Misra, A. K.; Tiwari, P.; Madhusudan, S. K. Carbohydr. Res. 2005, 340, 325.
8. Mukhopadhyay, B.; Russell, D. A.; Field, R. A. Carbohydr. Res. 2005, 340, 1075.
9. (a) Mukhopadhyay, B.; Collet, B.; Field, R. A. Tetrahedron Lett. 2005, 46, 5923.
10. (b) Du, Y.; Wei, G.; Cheng, S.; Hua, Y.; Linhardt, R. J. Tetrahedron Lett. 2006, 47, 307.
11. (a) Agarwal, A.; Rani, S.; Vankar, Y. D. J. Org. Chem. 2004, 69, 6137.
12. (b) Tiwari, P.; Agnihotri, G.; Misra, A. K. Carbohydr. Res. 2005, 340, 749.
13. (c) Misra, A. K.; Tiwari, P.; Agnihotri, G. Synthesis 2005, 260.
14. Das, B.; Reddy, M. R.; Ramu, R.; Reddy, K. R.; Geethangili, M. J. Chem. Res., Synop. 2005, 598.
15. Agarwal, A.; Vankar, Y. D. Carbohydr. Res. 2005, 340, 1661.
16. Khan, A. T.; Choudhury, L. H.; Ghosh, S. J. Mol. Cat. A: Chem. 2006, 255, 230.
17. Khan, A. T.; Ghosh, S.; Choudhury, L. H. Eur. J. Org. Chem. 2006, 2226.
18. Mondal, E.; Sahu, P. R.; Khan, A. T. Synlett 2002, 463.
19. Corey, E. J.; Niwa, H.; Knolle, J. J. Am. Chem. Soc. 1978, 100, 1942.
20. Miyashita, M.; Yoshikoshi, A.; Grieco, P. A. J. Org. Chem. 1977, 42, 3772.
21. Hoyer, S.; Laszlo, P.; Orlovic, M.; Polla, E. Synthesis 1986, 655.
22. Alper, H.; Dinkes, L. Synthesis 1972, 81.
23. Rezai, N.; Meybodi, F. A.; Salehi, P. Synth. Commun. 2000, 30, 1799.
24. Deka, N.; Sarma, J. C. Synth. Commun. 2000, 30, 4435.
25. Reddy, M. A.; Reddy, L. R.; Bhanumathi, N.; Rao, K. R. Synth. Commun. 2000, 30, 4323.
26. Hon, Y.-S.; Lee, C.-F.; Chen, R. J.; Szu, P.-H. Tetrahedron 2001, 57, 5991.
27. Naik, S.; Gopinath, R.; Patel, B. K. Tetrahedron Lett. 2001, 42, 7679.
28. Namboodiri, V. V.; Varma, R. S. Tetrahedron Lett. 2002, 43, 1143.
29. Stephens, J. R.; Butler, P. L.; Clow, C. H.; Oswald, M. C.; Smith, R. C.; Mohan, R. S. Eur. J. Org. Chem. 2003, 3827.
30. Namboodiri, V. V.; Verma, R. S. Chem. Commun. 2002, 342.
31. Yadav, J. S.; Subba Reddy, B. V.; Gnaneshwar, D. New J. Chem. 2003, 202.
32. Kavala, V.; Samal, A. K.; Patel, B. K. Arkivoc 2005, (i), 20; www.arkat-usa.org.
33. Khan, A. T.; Mondal, E.; Borah, B. M.; Ghosh, S. Eur. J. Org. Chem. 2003, 4113.
34. Khan, A. T.; Choudhury, L. H.; Ghosh, S. Tetrahedron Lett. 2004, 45, 7891.
35. Khan, A. T.; Ghosh, S.; Choudhury, L. H. Eur. J. Org. Chem. 2005, 4891.
36. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley: New York, 1999, 329-347.
37. Wilson, G. E. Jr.; Huang, M. G.; Schloman, W. W. Jr. J. Org. Chem. 1968, 33, 2133.
38. Yadav, V. K.; Fallis, A. G. Tetrahedron Lett. 1988, 29, 897.
39. Gogoi, S.; Borah, J. C.; Barua, N. C. Synlett 2004, 1592.
40. Khan, A. T.; Sahu, P. R.; Majee, A. J. Mol. Cat. A: Chem. 2005, 226, 207.
41. Firouzabadi, H.; Iranpoor, N.; Jafari, A. A.; Jafari, M. R. J. Mol. Cat. A: Chem. 2005, 247, 14.
42. Kamal, A.; Chouhan, G. Synlett 2002, 474.
43. Khan, A. T.; Mondal, E.; Ghosh, S.; Islam, S. Eur. J. Org. Chem. 2004, 2002.
44. Khan, A. T.; Mondal, E. Ind. J. Chem. 2005, 44B, 844.
45. Besra, R. C.; Rudrawar, S.; Chakraborti, A. K. Tetrahedron Lett. 2005, 46, 6213.
46. De, S. K. Adv. Synth. Cat. 2005, 347, 673.
47. Ali, M. H.; Gomes, M. G. Synthesis 2005, 1326.
48. Aoyama, T.; Takido, T.; Kodomari, M. Synlett 2004, 2307.
49. (a) Sartori, G.; Ballini, R.; Bigi, F.; Bosica, G.; Maggi, R.; Righi, P. Chem. Rev. 2004, 104, 199.
50. (b) Ong, B. S. Tetrahedron Lett. 1980, 21, 4225.