An efficient oxidative conversion of aldehydes into 2-substituted 2-oxazolines using 1,3-diiodo-5,5-dimethylhydantoin

Synthesis

Volumn , Issue 14, 2009, Pages 2329-2332

  Takahashi, Shogo ^a   Togo, Hideo ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

1,3 diiodo 5,5 dimethylhydantoin; 2 alkyl 2 oxazoline; 2 aminoethanol; 2 aryl 2 oxazoline; Aldehyde; Chiral oxazoline

Indexed keywords

1,3-DIIODO-5,5-DIMETHYLHYDANTOIN; 2-ALKYL-2-OXAZOLINE; 2-AMINOETHANOL; 2-ARYL-2-OXAZOLINE; CHIRAL OXAZOLINE;

ALDEHYDES; ALKYLATION; CHELATION; ORGANIC POLYMERS;

NITROGEN COMPOUNDS;

1,3 BIS[(4') 4' PHENYL 2' OXAZOLINE 2' YL]BENZENE; 1,3 DIIODO 5,5 DIMETHYLHYDANTOIN; 2 (1' ADAMANTYL) 2 OXAZOLINE; 2 (1' NAPHTHYL) 2 OXAZOLINE; 2 (2' PHENYLETHYL) 2 OXAZOLINE; 2 (2' PYRIDYL) 2 OXAZOLINE; 2 (2' THIENYL) 2 OXAZOLINE; 2 (4' BROMOPHENYL) 2 OXAZOLINE; 2 (4' CYANOPHENYL) 2 OXAZOLINE; 2 (4' METHOXYPHENYL) 2 OXAZOLINE; 2 (4' NITROPHENYL) 2 OXAZOLINE; 2 CYCLOHEXYL 2 OXAZOLINE; 2 HEPTYL 2 OXAZOLINE; 2 OXAZOLINE DERIVATIVE; 2 PHENYLGLYCINOL; 2,6 BIS[(4') 4' PHENYL 2' OXAZOLINE 2' YL]PYRIDINE; 4 2 (4' METHYLPHENYL) 4 PHENYL 2 OXAZOLINE; ALDEHYDE DERIVATIVE; BENZENE DERIVATIVE; ETHANOLAMINE; OXAZOLINE DERIVATIVE; PHENYTOIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; SYNTHESIS;

EID: 67651096139     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216843     Document Type: Article

References (57)

1. (a) Bergeron, R. J. Chem. Rev. 1984, 84, 587.
2. (b) Davidson, B. S. Chem. Rev. 1993, 93, 1771.
3. (c) Yeh, V. S. C. Tetrahedron 2004, 60, 11995.
4. (a) Boyd, G. V. In Comprehensive Heterocyclic Chemistry, Vol. 6; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984, 178-233.
5. (b) Gilman, A. G.; Goodman, L. S. The Pharmacological Basis of Therapeutics, 10th ed.; Macmillan & Co: New York, 2001.
6. (c) Genet, J. P.; Thorimbert, S.; Touzin, A. M. Tetrahedron Lett. 1993, 34, 1159.
7. (d) Wipf, P.; Venkatraman, S. Synlett 1997, 1.
8. (e) Rodriguez, A. D.; Ramirez, C.; Rodriguez, I. I.; Gonzalez, E. Org. Lett. 1999, 1, 527.
9. (f) Li, Q.; Woods, K. W.; Claiborne, A.; Gwaltney, S. L. H.; Barr, K. J.; Liu, G.; Gehrke, L.; Credo, R. B.; Hua-Hui, Y.; Lee, L.; Warner, R. B.; Kovar, P.; Nukkala, M. A.; Zielinski, N. A.; Tahir, S. K.; Fitzgerald, M.; Kim, K. H.; Marsh, K.; Frost, D.; Ng, S. C.; Rosenberg, S.; Fattorusso, C.; Catalanotti, B.; Ramunno, A.; Nacci, V.; Novellino, E.; Grewer, C.; Ionescu, D.; Rauen, T.; Griffiths, R.; Sinclair, C.; Fumagalli, E.; Mennini, T. J. Med. Chem. 2001, 44, 2507.
10. (g) Prisinzano, T.; Law, H.; Dukat, M.; Slassi, A.; MaClean, N.; Demchyshyn, L.; Glennon, R. A. Bioorg. Med. Chem. 2001, 9, 613.
11. (h) Brage, A. L.; Lüdtke, D. S.; Vargas, F.; Braga, R. C. Synlett 2006, 1453.
12. For examples: (a) Menges, F.; Neuburger, M.; Pfaltz, A. Org. Lett. 2002, 4, 4713.
13. (b) Evans, D. A.; Downey, C. W.; Hubbs, J. L. J. Am. Chem. Soc. 2003, 125, 8706.
14. (c) Bhor, S.; Anilkumar, G.; Tse, M. K.; Klawonn, M.; Döbler, C.; Bitterlich, B.; Grotevendt, A.; Beller, M. Org. Lett. 2005, 7, 3393.
15. For reviews: (a) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1.
16. (b) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
17. (c) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336.
18. (d) Meyers, A. I. J. Org. Chem. 2005, 70, 6137. For recent papers:
19. (e) Li, Y.; Feng, J.; Wang, W.; Chen, J.; Cao, X. J. Org. Chem. 2007, 72, 2344.
20. (f) Liu, H.; Xu, J.; Du, D. Org. Lett. 2007, 9, 4725.
21. (g) Schizuka, M.; Snapper, M. L. Angew. Chem. Int. Ed. 2008, 47, 5049.
22. (h) Nakamura, S.; Hirata, N.; Yamada, R.; Kita, T.; Shibata, N. Chem. Eur. J. 2008, 14, 5519.
23. (i) Sibi, M. P.; Nie, X.; Shackleford, J. P.; Stanley, L. M.; Bouret, F. Synlett 2008, 2655.
24. (a) Witte, H.; Seeliger, W. Angew. Chem., Int. Ed. Engl. 1972, 11, 287.
25. (b) Apple, R. Angew. Chem., Int. Ed. Engl. 1975, 14, 801.
26. (c) Lowenthal, A.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005.
27. (d) Zhou, P.; Blubarum, J. E.; Burns, C. T.; Natale, N. R. Tetrahedron Lett. 1977, 38, 7019.
28. (e) Vorbrüggen, H.; Krolikiewicz, K. Tetrahedron 1993, 49, 9353.
29. (f) Rajaram, S.; Sigman, M. S. Org. Lett. 2002, 4, 3399.
30. (g) Cwik, A.; Hell, Z.; Hegedüs, A.; Finta, Z.; Horvath, Z. Tetrahedron Lett. 2002, 43, 3985.
31. (h) Bandgar, B. P.; Pandit, S. S. Tetrahedron Lett. 2003, 44, 2331.
32. (i) Katritzky, A. R.; Cai, C.; Suzuki, K.; Singh, S. K. J. Org. Chem. 2004, 69, 811.
33. (j) Kangani, C. O.; Kelly, D. E. Tetrahedron Lett. 2005, 46, 8917.
34. (k) Mohammadpoor-Baltork, I.; Khosropour, A. R.; Hojati, S. F. Synlett 2005, 2747.
35. (l) Ohshima, T.; Iwasaki, J.; Mashima, K. Chem. Commun. 2006, 2711.
36. (m) Whelligan, D. K.; Bolm, C. J. Org. Chem. 2006, 71, 4609.
37. (n) Kangani, C. O.; Kelley, D. E.; Day, B. N. Tetrahedron Lett. 2006, 47, 6497.
38. (o) Fukuhara, T.; Hasegawa, C.; Hara, J. Synthesis 2007, 1528.
39. (p) May, A. E.; Willoughby, P. H.; Hoye, T. R. J. Org. Chem. 2008, 23, 3292.
40. (q) Chudasama, V.; Wilden, J. D. Chem. Commun. 2008, 3768.
41. (a) Fotadar, U.; Becu, C.; Borremans, F. A. M.; Anteunis, M. J. O. Tetrahedron 1978, 34, 3537.
42. (b) Feske, B. D.; Kaluzna, I. A.; Stewart, J. D. J. Org. Chem. 2005, 70, 9654.
43. (a) Minakarta, S.; Nishimura, M.; Takahashi, T.; Oderaotoshi, Y.; Komatsu, M. Tetrahedron Lett. 2001, 42, 9019.
44. (b) Nishimura, M.; Minakata, S.; Takahashi, T.; Oderaotoshi, Y.; Komatsu, M. J. Org. Chem. 2002, 67, 2101.
45. (c) Minakata, S.; Morino, Y.; Ide, T.; Oderaotoshi, Y.; Komatsu, M. Chem. Commun. 2007, 3279.
46. (a) Badiang, J. G.; Aubé, J. J. Org. Chem. 1996, 61, 2484.
47. (b) Chakraborty, R.; Franz, V.; Bez, G.; Vasadia, D.; Popuri, C.; Zhao, C. Org. Lett. 2005, 7, 4145.
48. Sayama, S. Synlett 2006, 1479.
49. Schwekendiek, K.; Glorius, F. Synthesis 2006, 2996.
50. Ishihara, M.; Togo, H. Tetrahedron 2007, 63, 1474.
51. (a) Ishihara, M.; Togo, H. Synlett 2006, 227.
52. (b) Ishihara, M.; Togo, H. Synthesis 2007, 1939.
53. (a) Iida, S.; Togo, H. Synlett 2007, 407.
54. (b) Iida, S.; Togo, H. Tetrahedron 2007, 63, 8274.
55. George, B.; Papadopoulos, E. P. J. Org. Chem. 1977, 42, 441.
56. Raush, D. M. Synth. Commun. 1985, 15, 675.
57. Poindexter, G. S. J. Heterocycl. Chem. 1983, 20, 1431.