Iodoxybenzoic acid (IBX): An efficient and novel oxidizing agent for the aromatization of 1,4-dihydropyridines

Synthesis

Volumn , Issue 3, 2006, Pages 451-454

  Yadav, J S ^a   Reddy, B V S ^a   Basak, A K ^a   Baishya, G ^a   Narsaiah, A Venkat ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aromatization; Dihydropyridines; DMSO; Hypervalent iodine reagents; Pyridine derivatives

Indexed keywords

AROMATIZATION; CATALYSTS; CHEMICAL REACTIONS; DERIVATIVES; SOLVENTS;

DIHYDROPYRIDINES; DMSO; HYPERVALENT IODINE REAGENTS; PYRIDINE DERIVATIVES;

CARBOXYLIC ACIDS;

1,4 DIHYDROPYRIDINE DERIVATIVE; BENZOIC ACID DERIVATIVE; DIMETHYL SULFOXIDE; IODINE DERIVATIVE; IODOXYBENZOIC ACID; OXIDIZING AGENT; PYRIDINE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CATALYSIS; HIGH TEMPERATURE; REACTION TIME;

EID: 32644444351     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918519     Document Type: Article

References (40)

1. IICT Communication No. 041107.
2. (a) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: London, 1997.
3. (b) Stang, P. J. J. Org. Chem. 2003, 68, 2997.
4. (c) Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537.
5. (d) Dess, B. D.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
6. (e) Hartman, C.; Meyer, V. Ber. Dtsch. Chem. Ges. 1893, 26, 1727.
7. (a) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. J. Am. Chem. Soc. 2004, 126, 5192.
8. (b) Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Narsaiah, A. V. Tetrahedron 2004, 60, 2131.
9. (c) Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019.
10. (d) Frigerio, M.; Santagostino, M.; Sputore, S.; Palmissano, G. J. Org. Chem. 1995, 60, 7272.
11. (e) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y. L. J. Am. Chem. Soc. 2002, 124, 2245.
12. (f) Nicolaou, K. C.; Baran, P. S.; Zhong, Y. L.; Vega, J. A. Angew. Chem. Int. Ed. 2000, 39, 2525.
13. (g) Bose, D. S.; Srinivas, P.; Gurjar, M. K. Tetrahedron Lett. 1997, 38, 5839.
14. (a) Brewster, M. E.; Simay, A.; Czako, K.; Winwood, D.; Fatag, H.; Bodor, N. J. Org. Chem. 1989, 54, 3721.
15. (b) Friedlos, F.; Knox, R. J. Biochem. Pharmacol. 1992, 44; 631.
16. (c) Stout, D. M.; Meyers, A. I. Chem. Rev. 1982, 82, 223.
17. (d) Janis, R. A.; Toggle, D. J. J. Med. Chem. 1983, 25, 775.
18. (e) Wei, X. Y.; Rulledge, A.; Triggle, D. J. J. Mol. Pharmacol. 1989, 35, 541.
19. (f) Bocker, R. H.; Guengerich, F. P. J. Med. Chem. 1986, 28, 1596.
20. (a) Wehinger, E.; Meyer, H.; Benz, U. Ger. Offen., DE 3209276, 1984; Chem. Abstr. 1984, 100, 22580;
21. Chem. Abstr. 1984, 100, 51454.
22. (b) Balogh, M.; Hermecz, I.; Kulcsar, G.; Meszaros, Z.; Virag, S.; Szutz, T.; Sebestyen, G. Belg. Patent, 889340, 1982; Chem. Abstr. 1982, 96, 85541.
23. (c) Treibs, W.; Beger, J. Ann. 1962, 652, 192.
24. (d) Ciba Ltd., Neth. Patent Appl., 6414307, 1966; Chem. Abstr. 1966, 64, 714.
25. (e) Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Narsaiah, A. V. Green Chem. 2003, 5.
26. (a) Kurtz, J. L.; Hutton, R.; Westheimer, F. H. J. Am. Chem. Soc. 1961, 33, 584.
27. (b) Zhu, X. Q.; Zhao, B. J.; Chang, J. P. J. Org. Chem. 2000, 65, 8158.
28. (c) Yadav, J. S.; Reddy, B. V. S.; Sabitha, G.; Garudammagari, S.; Reddy, K. K. Synthesis 2000, 1532.
29. (d) Bocker, R. H.; Guengerich, F. P. J. Med. Chem. 1986, 28, 1596.
30. (e) Itoh, T.; Nagata, K.; Okada, M.; Ohsawa, A. Tetrahedron Lett. 1995, 36, 2269.
31. (f) Balogh, M.; Hermecz, I.; Meszaros, Z.; Laszlo, P. Helv. Chim. Acta 1984, 67, 2270.
32. (g) Maquestiau, A.; Mayence, A.; Eynde, J. J. V. Tetrahedron Lett. 1991, 32, 3839.
33. (h) Anniyappan, M.; Muralidharan, D.; Perumal, T. P. Tetrahedron 2002, 58, 5069.
34. (i) Pfister, J. R. Synthesis 1990, 689.
35. (j) Eynde, J. J. V.; Mayence, A.; Maquestiau, A. Tetrahedron 1992, 48, 463.
36. (a) Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Narsaiah, A. V. Tetrahedron Lett. 2003, 44, 2217.
37. (b) Yadav, J. S.; Reddy, B. V. S.; Sadashiv, K.; Harikishan, K.; Narsaiah, A. V. J. Mol. Catal. A. 2004, 220, 153.
38. (c) Yadav, J. S.; Reddy, B. V. S.; Reddy, P. S. R.; Basak, A. K.; Narsaiah, A. V. Adv. Synth. Catal. 2004, 346, 77.
39. (d) Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Narsaiah, A. V.; Prabhakar, A.; Jagadeesh, B. Tetrahedron Lett. 2005, 46, 639.
40. (e) Yadav, J. S.; Reddy, B. V. S.; Baishya, G.; Narsaiah, A. V. Chem. Lett. 2005, 1, 102.