Fluoroboric acid adsorbed on silica-gel (HBF4-SiO2) as a new, highly efficient and reusable heterogeneous catalyst for thia-Michael addition to α,β-unsaturated carbonyl compounds

Tetrahedron Letters

Volumn 49, Issue 27, 2008, Pages 4272-4275

  Sharma, Gaurav ^a   Kumar, Raj ^a   Chakraborti, Asit K ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

, Unsaturated carbonyl; Benzothiazepines; HBF4 SiO2; Heterogeneous catalyst; Thia Michael addition; Thiol

Indexed keywords

1,3 DIARYL 2 PROPENONE DERIVATIVE; ALPHA,BETA UNSATURATED CARBONYL DERIVATIVE; BORIC ACID; CARBONYL DERIVATIVE; FLUOROBORIC ACID; KETONE DERIVATIVE; METHANOL; SILICA GEL; SOLVENT; THIOL DERIVATIVE;

ADSORPTION; ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; MICHAEL ADDITION; MOLECULAR INTERACTION; ONE POT SYNTHESIS;

THIA;

EID: 44349125058     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.04.144     Document Type: Article

References (46)

1. Fujita E., and Nagao Y. Bioorg. Chem. 6 (1977) 287-309
2. Fluharty A.L. In: Patai S. (Ed). The Chemistry of the Thiol Group, Part 2 (1974), Wiley Interscience, New York 589
3. Trost B.M., and Keeley D.E. J. Org. Chem. 40 (1975) 2013
4. Kumar A., Salunkhe R.V., Rane R.A., and Dike S.Y. J. Chem. Soc., Chem. Commun. (1991) 485-486
5. Cohen T., Mura Jr. A.J., Shull D.W., Fogel E.R., Ruffner R.J., and Falck J.R. J. Org. Chem. 41 (1976) 3218-3219
6. Bakuzia P., and Bakuzis M.L.F. J. Org. Chem. 46 (1981) 235-239
7. Cherkauskas J.P., and Cohen T. J. Org. Chem. 57 (1992) 6-8
8. Recent examples:. Chu C.-M., Gao S., Sastry M.N.V., Kuo C.-W., Lu C., Liu J.-T., and Yao C.-F. Tetrahedron 63 (2007) 1863-1871
9. Hussain S., Bharadwaj S.K., Chaudhuri M.K., and Kalita H. Eur. J. Org. Chem. (2007) 374-378
10. Chu C.-M., Huang W.-J., Lu C., Wu P., Liu J.-T., and Yao C.-F. Tetrahedron Lett. 47 (2006) 7375-7380
11. Karodia N., Liu X., Ludley P., Pletsas D., and Stevenson G. Tetrahedron 62 (2006) 11039-11043
12. Maria M., and Stefan T. Lett. Org. Chem. 3 (2006) 794-797
13. Kumarraja M., and Pitchumani K. J. Mol. Catal. A: Chem. 256 (2006) 138-142
14. Pore D.M., Saodagar M.S., Desai U.V., Thopate T.S., and Wadagaonkar P.P. Tetrahedron Lett. 47 (2006) 9325-9328
15. Khan A.T., Ghosh S., and Choudhary L.H.. Eur. J. Org. Chem. (2006) 2226-2231
16. Firouzabadi H., Iranpoor N., Jafarpour M., and Ghaderi A. Tetrahedron Lett. 249 (2006) 98-102
17. Zahouily M., Mounir B., Charki H., Mezdar A., Bahlaouan B., and Ouammou M. ARKIVOC xiii (2006) 178-186
18. Yang L., Xu L.-W., and Xia C.-G. Tetrahedron Lett. 46 (2005) 3279-3282
19. Krishnaveni N.K., Surendra K., and Rao K.R. Chem. Commun. (2005) 669-671
20. Chu C.-M., Gao S., Sastry M.N.V., and Yao C.-F. Tetrahedron Lett. 46 (2005) 4971-4974
21. Zhang H., Zhang Y., Liu L., Xu H., and Wang Y. Synthesis (2005) 2129-2136
22. Ranu B.C., Dey S.S., and Samanta S. ARKIVOC iii (2005) 44-50
23. Firouzabadi H., Iranpoor N., and Jafari A.A. Adv. Synth. Catal. 347 (2005) 655-661
24. Firouzabadi, H.; Iranpoor, N.; Jafari, A. A. Synlett 2005, 299-303.
25. Garg S.K., Kumar R., and Chakraborti A.K. Tetrahedron Lett. 46 (2005) 1721-1724
26. Garg S.K., Kumar R., and Chakraborti A.K. Synlett (2005) 1370-1374
27. Khatik G.L., Kumar R., and Chakraborti A.K. Org. Lett. 8 (2006) 2433-2436
28. Sharma G., Kumar R., and Chakraborti A.K. J. Mol. Catal. A: Chem. 263 (2007) 143-148
29. Clark J.H. Green Chem. (1999) 1-8
30. Anastas P.T., Bartlett L.B., Kirchhoff M.M., and Williamson T.C. Catal. Today 55 (2000) 11-22
31. Clark J.H. Pure Appl. Chem. 73 (2001) 103-111
32. Wilson K., and Clark J.H. Pure Appl. Chem. 72 (2000) 1313-1319
33. Kumar R., Kumar D., and Chakraborti A.K. Synthesis (2007) 299-303
34. Rudrawar S., Besra R.C., and Chakraborti A.K. Synthesis (2006) 2767-2771
35. Chakraborti A.K., and Chankeshwara S.V. Org. Biomol. Chem. 4 (2006) 2769-2771
36. Chankeshwara S.V., and Chakraborti A.K. J. Mol. Catal. A: Chem. 253 (2006) 198-202
37. Chakraborti A.K., Kondaskar A., and Rudrawar S. Tetrahedron 60 (2004) 9085-9091
38. Chakraborti A.K., Rudrawar S., and Kondaskar A. Org. Biomol. Chem. 2 (2004) 1277-1280
39. Chakraborti A.K., and Gulhane R. J. Chem. Soc., Chem. Commun. (2003) 1896-1897
40. Chakraborti A.K., and Gulhane R. Tetrahedron Lett. 44 (2003) 3521-3525
41. 11h (Chakraborti, A. K.; Gulhane, R. Indian Patent, 266/DEL/2003 (10-3-2003)).
42. Gao S., Tzeng T., Sastry M.N.V., Chu C.-M., Liu J.-T., Lin C., and Yao C.-F. Tetrahedron Lett. 47 (2006) 1889-1893
43. Chakraborti A.K., Bhagat S., and Rudrawar S. Tetrahedron Lett. 45 (2004) 7641-7644
44. Khatik G.L., Kumar R., and Chakraborti A.K. Synthesis (2007) 541-546
45. Khatik G.L., Kumar R., and Chakraborti A.K. Tetrahedron 63 (2007) 1200-1210
46. 2 (0.05 g, 0.025 mmol, 1 mol %) and the reaction mixture was stirred at rt (∼25-30 °C) until completion of the reaction (5 min: TLC, IR).