Lewis acid-catalyzed Friedel-Crafts alkylations of 3-hydroxy-2-oxindole: An efficient approach to the core structure of azonazine

Chemical Communications

Volumn 48, Issue 81, 2012, Pages 10132-10134

  Ghosh, Santanu ^a   Kinthada, Lakshmana K ^a   Bhunia, Subhajit ^a   Bisai, Alakesh ^a  

^a INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH BHOPAL   (India)

Author keywords

[No Author keywords available]

Indexed keywords

3 ALKYL 3 HYDROXY 2 OXINDOLE; 3 HYDROXY 2 OXINDOLE; ANTIINFLAMMATORY AGENT; AZONAZINE; CARBON; LEWIS ACID; OXINDOLE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; ENANTIOSELECTIVITY; FRIEDEL CRAFTS REACTION; METHYLATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

EID: 84866432553     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc35283d     Document Type: Article

References (45)

1. G. A. Olah, Friedel-Crafts and Related Reactions, Wiley-Interscience, New York, 1963
2. G. A. Olah, R. Krishnamurti and G. K. S. Prakash, In Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 3, ch. 1.8, pp. 293-339
3. G. R. Meima, G. S. Lee and J. M. Garces, in Friedel-Crafts Alkylation, ed. R. A. Sheldon and H. Bekkum, Wiley-VCH, New York, 2001, pp. 151-160
4. A. Baeyer, M. J. Lazarus, Ber. Dtsch. Chem. Ges. 1885, 18, 2637
5. D. A. Klumpp, K. Yeung, G. K. S. Prakash, G. A. Olah, J. Org. Chem. 1998, 63, 4481
6. M. Bandini, A. Melloni, A. Umani-Ronchi, Angew. Chem. Int. Ed. 2004, 43, 550
7. M. Bandini, A. Melloni, S. Tommasi, A. Umani-Ronchi, Synlett, 2005, 1199
8. T. Poulsen, K. A. Jorgensen, Chem. Rev. 2008, 108, 2903
9. S. -L. You, Q. Cai, M. Zeng, Chem. Soc. Rev. 2009, 38, 2190
10. N. Lindquist, W. Van Duyne, G. D. Fenical, J. Clardy, J. Am. Chem. Soc. 1991, 113, 2303
11. Z. Cruz-Monserrate, H. C. Vervoort, R. Bai, D. J. Newman, S. B. Howell, G. Los, J. T. Mullaney, M. D. Williams, G. R. Pettit, W. Fenical, E. Hamel, Mol. Pharmacol. 2003, 63, 1273
12. Z. Cruz-Monserrate, J. T. Mullaney, P. G. Harran, G. R. Pettit, E. Hamel, Eur. J. Biochem. 2003, 270, 3822
13. A. W. G. Burgett, Q. Li, Q. Wei, P. G. Harran, Angew. Chem. Int. Ed. 2003, 42, 4961
14. K. C. Nicolaou, S. A. Snyder, X. Huang, K. B. Simonsen, A. E. Koumbis, A. Bigot, J. Am. Chem. Soc. 2004, 126, 10162
15. R. R. Knowles, J. Carpenter, S. B. Blakey, A. Kayano, I. K. Mangion, C. J. Sinz, D. W. C. MacMillan, Chem. Sci. 2011, 2, 308
16. E. Vedejs, D. A. Barda, Org. Lett. 2000, 2, 1033
17. D. E. Fuerst, B. M. Stoltz, J. L. Wood, Org. Lett. 2000, 2, 3521
18. P. Wipf, J.-L. Methot, Org. Lett. 2001, 3, 1261
19. K. S. Feldman, K. J. Eastman, G. Lessene, Org. Lett. 2002, 4, 3525
20. C. Poriel, M. Lachia, C. Wilson, J. R. Davies, C. J. Moody, J. Org. Chem. 2007, 72, 2978
21. J. Lin, B. S. Gerstenberger, N. Y. T. Steeman, J. P. Konopelski, Org. Lett. 2008, 10, 3969
22. J. Zhang, M. A. Ciufolini, Org. Lett. 2011, 13, 390
23. Q.-X. Wu, M. S. Crew, M. Draskovic, J. Sohn, T. A. Johnson, K. Tenney, F. A. Valeriote, X.-J. Yao, L. F. Bjeldanes, P. Crews, Org. Lett. 2010, 12, 4458
24. Q. X. Wu, A. M. Yang, Y. P. Shi, Tetrahedron, 2005, 61, 10529
25. T. D. Gilmore, Oncogene, 2006, 25, 6680
26. L. H. Naylor, Biochem. Pharmacol. 1999, 58, 749
27. M. Tachibana, C. Matsui, Y. Takeuchi, E. Suzuki, K. Umezawa, Heterocycles, 2008, 76, 1561
28. H. Z. Jin, B. Y. Hwang, H. S. Kim, J. H. Lee, Y. H. Kim, J. J. Lee, J. Nat. Prod. 2002, 65, 89
29. Z. Rappoport, The chemistry of phenols; John Wiley and Sons, New York, 2003
30. H. Heaney, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, UK, 1991, vol. 2, pp. 733-752
31. D. B. England, G. Merey, A. Padwa, Org. Lett. 2007, 9, 3805
32. F. Zhou, Z.-Y. Cao, J. Zhang, H.-B. Yang, J. Zhou, Chem.-Asian J. 2012, 7, 233
33. C. Menozzi, P. I. Dalko, J. Cossy, Chem. Commun. 2006, 4638
34. F. W. Goldberg, P. Magnus, R. Turnbull, Org. Lett. 2005, 7, 4531
35. P. Magnus, R. Turnbull, Org. Lett. 2006, 8, 3497
36. K. C. Nicolaou, J. Hao, M. V. Reddy, P. Bheema Rao, G. Rassias, S. A. Snyder, X. Huang, D. Y. -K. Chen, W. E. Brenzovich, N. Guiseppone, P. Giannakakou, A. O’Brate, J. Am. Chem. Soc. 2004, 126, 12897
37. Quaternary Stereocenters. Challenges and Solutions in Organic Synthesis, ed. J. Christoffers and A. Baro, Wiley, 2006
38. V. B. Birman, S. J. Danishefsky, J. Am. Chem. Soc. 2002, 124, 2080
39. J. T. Mohr, M. R. Krout, B. M. Stoltz, Nature, 2008, 455, 323
40. C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5363
41. J. F. Austin, S.-G. Kim, C. J. Sinz, W.-J. Xiao, D. W. C. MacMillan, Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5482
42. C.-K. Mai, M. F. Sammons, T. Sammakia, Org. Lett. 2010, 12, 2306
43. E. J. Corey, A. Guzman-Perez, Angew. Chem. Int. Ed. 2003, 42, 4961
44. F. Zhou, Y.-L. Liu, J. Zhou, Adv. Synth. Catal. 2010, 352, 1381
45. S. Ma, X. Han, S. Krishnan, S. C. Virgil, B. M. Stoltz, Angew. Chem. Int. Ed. 2009, 48, 8037