One-pot synthesis of highly functionalized oxindoles under swern oxidation conditions

Synlett

Volumn , Issue 18, 2007, Pages 2792-2796

  López Alvarado, Pilar ^a   Steinhoff, Judith ^a   Miranda, Sonia ^a   Avendaño, Carmen ^a   Menéndez, J Carlos ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Halogenation; Indoles; Oxidation; Oxindole synthesis; Swern reaction

Indexed keywords

CHLORINE; DIMETHYL SULFOXIDE; HYDROXYL GROUP; INDOLE DERIVATIVE; OXINDOLE;

ARTICLE; ONE POT SYNTHESIS; OXIDATION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SWERN OXIDATION; SYNTHESIS;

EID: 36549059077     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990955     Document Type: Article

References (37)

1. Tokunaga, T.; Hume, W. E.; Nagamine, J.; Kawamura, T.; Taiji, M.; Nagata, R. Bioorg. Med. Chem. Lett. 2005, 15, 1789.
2. (a) Smith, C. D.; Zilfou, J. T.; Stratmann, K.; Patterson, G. M. L.; Moore, R. E. Mol. Pharmacol. 1995, 47, 241.
3. (b) Zhang, X.; Smith, C. D. Mol. Pharmacol. 1996, 49, 288.
4. Zaveri, N. T.; Jiang, F.; Olsen, C. M.; Deschamps, J. R.; Parrish, D.; Polgar, W.; Toll, L. J. Med. Chem. 2004, 47, 2973.
5. Alcaraz, M.; Atkinson, S.; Cornwall, P.; Foster, A. C.; Gill, D. M.; Humphries, L. A.; Keegan, P. S.; Kemp, R.; Merifield, E.; Nixon, R. A.; Noble, A. J.; O'Beirne, D.; Patel, Z. M.; Perkins, J.; Rowa, P.; Sadler, P.; Singleton, J. T.; Tornos, J.; Watts, A. J.; Woodland, I. A. Org. Process Res. Dev. 2005, 9, 555.
6. Kikuchi, C.; Hiranuma, T.; Koyama, M. Bioorg. Med. Chem. Lett. 2002, 12, 2549.
7. Gallagher, G.; Lavanchi, P. G.; Wilson, J. W.; Hieble, J. P.; DeMarinis, R. M. J. Med. Chem. 1985, 28, 1533.
8. For early surveys of oxindole alkaloids, see: (a) Cordell, G. A. An Introduction to Alkaloids: A Biogenetic Approach; Wiley-Interscience: New York, 1981.
9. (b) Bindra, J. S. Oxindole Alkaloids, In The Alkaloids - Chemistry and Physiology, Vol. 14; Manske, R. H. F., Ed.; Academic Press: New York, 1973, 83.
10. Abourriche, A.; Abboud, Y.; Maoufoud, S.; Mohou, H.; Seffaj, T.; Charrouf, M.; Chaib, N.; Benamara, A.; Bontemps, N.; Francisco, C. Farmaco 2003, 58, 1351.
11. (a) Isolation: Cui, C. B.; Kakeya, H.; Okada, G.; Onose, R.; Osada, H. J. Antibiot. 1996, 49, 527.
12. (b) Structure: Cui, C.; Kakeya, H.; Osada, H. Tetrahedron 1996, 52, 12651.
13. Total syntheses: (c) Edmonson, S.; Danishefsky, S. J. Angew. Chem. Int. Ed. 1998, 37, 1138.
14. (d) Wang, H.; Ganesan, A. J. Org. Chem. 2000, 65, 4685.
15. (e) Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666.
16. (f) Von Nussbaum, F.; Danishefsky, S. J. Angew. Chem. Int. Ed. 2000, 39, 2175.
17. (g) Cytotoxic activity: Edmondson, S. E.; Danishefsky, S. J.; Sepp-Lorenzino, L.; Rosen, N. J. Am. Chem. Soc. 1999, 121, 2147.
18. For reviews of the chemistry of the welwitindolinones, see: (a) Avendaño, C.; Menéndez, J. C. Curr. Org. Synth. 2004, 1, 65.
19. (b) Menéndez, J. C. In Bioactive Heterocycles V, In Topics in Heterocyclic Chemistry, Vol. 11; Springer: Berlin/Heidelberg, 2007, 63.
20. (a) Szabo-Pusztay, K.; Szabo, L. Synthesis 1979, 276.
21. (b) Underwood, R.; Prasad, K.; Repic, O.; Hardtmann, G. Synth. Commun. 1992, 22, 343.
22. (c) Cushing, T. D.; Sanz-Cervera, J. F.; Williams, R. M. J. Am. Chem. Soc. 1993, 115, 9323.
23. For a review of the synthesis of 2-oxindoles, see: Karp, G. M. Org. Prep. Proced. Int. 1993, 25, 481.
24. Bailey, P. D.; Cochrane, P. J.; Irvine, F.; Morgan, K. M.; Pearson, D. P. J.; Veal, K. T. Tetrahedron Lett. 1999, 40, 4593.
25. Some of these compounds are known in the literature. See: Harrington, P. E.; Kerr, M. A. Synlett 1996, 1047.
26. Wuest, F. R.; Kniess, T. J. Labelled Compd. Radiopharm. 2005, 48, 31.
27. 4) and evaporated, and the residue was purified by rapid chromatography on silica gel, eluting with PE-EtOAc mixtures (gradient from 20:1 to 5:1), to yield compound 8b (357 mg, 90%). Slower chromatographic separation may lead to considerable amounts of decomposition products, specially from hydrolysis of the terminal chloromethylene moiety.
28. 2: C, 54.18; H, 5.25; N, 4.86. Found: C, 53.95; H, 5.12; N, 4.75.
29. 4Cl. See: (a) Hino, T.; Miura, H.; Nakagawa, T.; Murata, R.; Nakagawa, M. Heterocycles 1975, 3, 805.
30. (b) Hino, T.; Miura, H.; Murata, R.; Nakagawa, M. Chem. Pharm. Bull. 1978, 26, 3695.
31. 2: C, 62.03; H, 5.61; N, 5.56. Found: C, 62.35; H, 5.81; N, 5.62.
32. 2O at -20°C for 5 h, which gave the corresponding five-membered spirolactones in yields of around 65% as mixtures of diastereomers. See: (a) Büchi, G.; DeShong, P. R.; Katsumura, S.; Sagimura, Y. J. Am. Chem. Soc. 1979, 101, 5084.
33. For a similar reaction using a mixture of DMSO and tert-butyl bromide, see: (b) Palla, G.; Marchelli, R.; Casnati, G.; Dossena, A. Gazz. Chim. Ital. 1982, 112, 535.
34. (c) Labroo, R. B.; Labroo, V. M.; King, M. M.; Cohen, L. A. J. Org. Chem. 1991, 56, 3637.
35. Indeed, compounds 8 were not obtained when oxalyl chloride was replaced by TFAA.
36. Nozoye, T.; Shibanuma, Y.; Nakai, T.; Hatori, H. Chem. Pharm. Bull. 1988, 36, 4980.
37. McComas, C. C.; Perales, J. B.; Van Vranken, D. L. Org. Lett. 2002, 3, 2337.