An efficient and novel synthesis of chromonyl chalcones using recyclable Zn(l-proline)2 catalyst in water

Tetrahedron Letters

Volumn 52, Issue 31, 2011, Pages 4008-4013

  Siddiqui, Zeba N ^a   Musthafa, T N Mohammed ^a  

^a ALIGARH MUSLIM UNIVERSITY   (India)

Author keywords

3 Formylchromones; Green synthesis; Heterochalcones; Zn(l proline)2

Indexed keywords

3 ACETYL 4 HYDROXYCOUMARIN; 3 FORMYLCHROMONE DERIVATIVE; 6 CHLORO 3 FORMYLCHROMONE; CHALCONE DERIVATIVE; CHROMONE DERIVATIVE; CHROMONYL CHALCONE; LEWIS ACID; METHYL GROUP; UNCLASSIFIED DRUG; WATER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR WEIGHT; PROTON NUCLEAR MAGNETIC RESONANCE;

PUFFINUS AURICULARIS;

EID: 79959883229     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.05.118     Document Type: Article

References (52)

1. P.M. Dewick The Flavonoids: Advances in Research since 1986 J.B. Harborne, 1994 Chapmann & Hall New York p. 38
2. P. Valenti, A. Bisi, A. Rampa, F. Belluti, S. Gobbi, A. Zampiron, and M. Carrara Bioorg. Med. Chem. 8 2000 239 246
3. A. Boumendjel, F. Bois, C. Beney, A.M. Mariotte, G. Conseil, and A. Di Petro Bioorg. Med. Chem. Lett. 11 2001 75 77
4. R. Larget, B. Lockhart, P. Renard, and M. Largeron Bioorg. Med. Chem. Lett. 10 2000 835 838
5. A. Groweiss, J.H. Cardellins, and M.R. Boyd J. Nat. Prod. 63 2000 1537 1539
6. A. Gross, D.R. Borcherding, D. Friedrich, and J.S. Sabol Tetrahedron Lett. 42 2001 1631 1633
7. O. Prakash, R. Kumar, and V. Parkash Eur. J. Med. Chem. 43 2008 435 440
8. Z. Nowakowska Eur. J. Med. Chem. 42 2007 125 137
9. O. Prakash, A. Kumar, A. Sadana, R. Prakash, P.S. Singh, M.R. Claramunt, D. Sanz, I. Alkortac, and J. Elgueroc Tetrahedron 61 2005 6642 6651
10. R.Y. Prasad, L.A. Rao, L. Prasoona, K. Murali, and R.P. Kumar Bioorg. Med. Chem. Lett. 15 2005 5030 5034
11. S. Raghavan, and K. Anuradha Tetrahedron Lett. 43 2002 5181 5183
12. B.A. Bohm Introduction to Flavonoids 1998 Harwood Academic Amsterdam
13. D.N. Dhar Chemistry of Chalcones and Related Compounds 1981 Wiley New York
14. S.F. Nielsen, S.B. Christensen, G. Cruciani, A. Kharazmi, and T. Liljefors J. Med. Chem. 41 1998 4819 4832
15. F. Micheli, F. Degiorgis, A. Feriani, A. Paio, A. Pozzan, P. Zarantonello, and P. Seneci J. Comb. Chem. 3 2001 224 228
16. X. Bu, L. Zhao, and Y. Li Synthesis 1997 1246 1248
17. X. Bu, and Y. Li J. Nat. Prod. 59 1996 968 969
18. A.R. Alcantara, J.M. Marinas, and J.V. Sinisterra Tetrahedron Lett. 28 1987 1515 1518
19. M.J. Climent, A. Corma, S. Iborra, and A. Velty J. Catal. 221 2004 474 482
20. J.B. Daskiewicz, G. Comte, D. Barron, A.D. Pietro, and F. Thomasson Tetrahedron Lett. 40 1999 7095 7098
21. S. Sebti, A. Solhy, R. Tahir, S. Boulaajaj, J.A. Mayoral, J.M. Fraile, A. Kossir, and H. Oumimoun Tetrahedron Lett. 42 2001 7953 7955
22. S. Sebti, A. Solhy, A. Smahi, A. Kossir, and H. Oumimoun Catal. Commun. 2002 335 339
23. N.O. Calloway, and L.D. Green J. Am. Chem. Soc. 59 1937 809 811
24. T. Szell, and I. Sohalr Can. J. Chem. 47 1969 1254 1258
25. K. Irie, and K. Watanabe Bull. Chem. Soc. Jpn. 53 1980 1366 1371
26. L. Mazza, and A. Guaram Synthesis 1980 41 44
27. T. Nakano, S. Irifune, S. Umano, A. Inada, Y. Ishii, and M. Ogawa J. Org. Chem. 52 1987 2239 2244
28. N. Iranpoor, and F. Kazemi Tetrahedron 54 1998 9475 9480
29. I.T. Horvath Green Chem. 10 2008 1024 1028
30. B.H. Lipshutz, and S. Ghorai Aldrichim. Acta 41 2008 59 72
31. R.A. Sheldon Green Chem. 7 2005 267 278
32. C.J. Li, and T.H. Chan Organic Reactions in Aqueous Media 1997 Wiley New York
33. P.A. Grieco Organic Synthesis in Water 1997 Academic Press Dordrecht, The Netherlands
34. K.H. Shaughnessy, and R.B. DeVasher Curr. Org. Chem. 9 2005 585 604
35. T. Darbre, and M. Machuqueiro Chem. Commun. 9 2003 1090 1091
36. J. Kofoed, M. Machuqueiro, J.L. Reymond, and T. Darbre Chem. Commun. 2004 1540 1541
37. V. Sivamurugan, K. Deepa, M. Palanichamy, and V. Murugesan Synth. Commun. 34 2004 3833 3846
38. V. Sivamurugan, R.S. Kumar, M. Palanichamy, and V. Murugesan J. Heterocycl. Chem. 42 2005 969 974
39. J. Kofoed, J.L. Reymond, and T. Darbre Org. Biomol. Chem. 3 2005 1850 1855
40. F.L. Ruben, J. Kofoed, M. Machuqueiro, and T. Darbre Eur. J. Org. Chem. 2005 5268 5276
41. V. Sivamurugan, A. Vinu, M. Palanichamy, and V. Murugesan Heteroat. Chem. 17 2006 267 271
42. J. Kofoed, T. Darbre, and J.L. Reymond Chem. Commun. 14 2006 1482 1484
43. K.R. Reddy, C.V. Rajasekhar, and G.G. Krishna Synth. Commun. 37 2007 1971 1976
44. M.M. Heravi, M.H. Tehrani, K. Bakhtiari, and H.A. Oskooie Catal. Commun. 8 2007 1341 1344
45. M. Kidwai, A. Jain, and S. Bhardwaj Catal. Lett. 141 2011 183 190
46. M. Kidwai, A. Jain, and R. Poddar J. Organomet. Chem. 696 2011 1939 1944
47. Z.N. Siddiqui, M. Asad, and S. Praveen Med. Chem. Res. 17 2008 318 325
48. Musthafa, T. N. M.; Siddiqui, Z. N.; Husain, F. M.; Ahmad, I. Med. Chem. Res. 2010 doi:10.1007/s00044-010-9386-2.
49. Siddiqui, Z. N.; Praveen, S.; Musthafa, T. N. M.; Ahmad, A.; Khan, A. U. J. Enz. Inhib. Med. Chem. 2011. doi:10.3109/14756366.2011.577035.
50. Z.N. Siddiqui, T.N.M. Musthafa, S. Praveen, and F. Farooq Med. Chem. Res. 2010 10.1007/s00044-010-9376-4
51. 2 complex was obtained as white solid, was filtered and dried. Yield: 91%.
52. 4, concentrated to furnish crude product, which was then recrystallized from chloroform or methanol-DMF mixture. The catalyst was recovered by precipitating the aqueous layer by addition of acetone. The catalyst recovered from the aqueous layer was used for the subsequent cycle.