Construction of 3,5-substituted 1,2,4-oxadiazole rings triggered by tetrabutylammonium hydroxide: A highly efficient and fluoride-free ring closure reaction of O-acylamidoximes

Tetrahedron Letters

Volumn 55, Issue 5, 2014, Pages 979-981

  Otaka, Hiromichi ^a   Ikeda, Junya ^a   Tanaka, Daisuke ^a   Tobe, Masanori ^a  

^a DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

Author keywords

1,2,4 Oxadiazole; O Acylamidoxime; Tetrabutylammonium fluoride; Tetrabutylammonium hydroxide

Indexed keywords

1,2,4 OXADIAZOLE DERIVATIVE; 3,5 SUBSTITUTED 1,2,4 OXADIAZOLE; FLUORIDE; O ACYLAMIDOXIME DERIVATIVE; OXIME DERIVATIVE; TETRABUTYLAMMONIUM; TETRABUTYLAMMONIUM HYDROXIDE; UNCLASSIFIED DRUG; ACETYLBENZAMIDOXIME; OXADIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTOR; ROOM TEMPERATURE; SYNTHESIS; CATALYST;

EID: 84892817253     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.12.016     Document Type: Article

References (32)

1. A. Pace, and P. Pierro Org. Biomol. Chem. 7 2009 4337 4348
2. J. Boström, A. Hogner, A. Llinàs, E. Wellner, and A.T. Plowright J. Med. Chem. 55 2012 1817 1830
3. J.W. Clitherow, P. Beswick, W.J. Irving, D.I.C. Scopes, J.C. Barnes, J. Clapham, J.D. Brown, D.J. Evans, and A.G. Hayes Bioorg. Med. Chem. Lett. 6 1996 833 838
4. K.E. Andersen, B.F. Lundt, A.S. Jørgensen, and C. Braestrup Eur. J. Med. Chem. 31 1996 417 425
5. S. Borg, G. Estenne-Bouhtou, K. Luthman, I. Csoregh, W. Hesselink, and U. Hacksell J. Org. Chem. 60 1995 3112 3120
6. T. Naka, and K. Kubo Curr. Pharm. Des. 5 1999 453 472
7. G.D. Diana, D.L. Volkots, J.T. Nitz, R.T. Bailey, M.A. Long, N. Vescio, S. Aldous, D.C. Peveur, and F.J. Dutko J. Med. Chem. 37 1994 2421 2436
8. S. Borg, R.C. Vollinga, M. Labarre, K. Payza, L. Terenius, and K. Luthman J. Med. Chem. 42 1999 4331 4342
9. J.M. Filho, A.C.L. Leite, B.G. de Oliveria, D.R.M. Moreira, M.S. Lima, M.B.P. Soares, and L.F. Leite Bioorg. Med. Chem. 17 2009 6682 6691
10. L.J. Street, R. Baker, T. Book, C.O. Kneen, A.M. MacLeod, K.J. Merchant, G.A. Showell, J. Saunders, R.H. Herbert, S.B. Freedman, and E.A. Harley J. Med. Chem. 33 1990 2690 2697
11. Diana, G. D.; Nitz, T. J. U.S. Patent US 5464848, 1995.
12. R.A. Fromtling, and J. Castañer Drugs Future 22 1997 40 44
13. Lanier, M.; Luo, Z.; Moorjani, M.; Tellew, J. E.; Williams, J. P.; Zhang, X. PCT Int. Appl. WO 2006044958, 2006.
14. J.E. Tellew, M. Lanier, and M. Moorjani et al. Bioorg. Med. Chem. Lett. 20 2010 7259 7264
15. M. Carbone, Y. Li, C. Irace, E. Mollo, F. Castelluccio, A. Di Pascale, G. Cimino, R. Santamaria, Y.W. Guo, and M. Gavagnin Org. Lett. 13 2011 2516 2519
16. R. Agneeswari, V. Tamilavan, M. Song, J.W. Kang, S.H. Jin, and M.H. Hyun J. Polym. Sci., Part A: Polym. Chem. 51 2013 2131 2141
17. M. Parra, P. Hidalgo, E. Carrasco, J. Barbera, and L. Silvino Liq. Cryst. 33 2006 875 882
18. J.C. Jung, and E.J. Choi Angew. Macromol. Chem. 197 1992 73 82
19. F. Tiemann, and P. Kruger Chem. Ber. 17 1884 1685 1698
20. N.S. Ooi, and D.A. Wilson J. Chem. Soc., Perkin Trans. 2 1980 1792 1799
21. K. Tabei, E. Kawashima, T. Takada, and T. Kato Chem. Pharm. Bull. 30 1982 336 340
22. S. Chiou, and H.J. Shine J. Heterocycl. Chem. 26 1989 125 128
23. G.B. Liang, and D.D. Feng Tetrahedron Lett. 37 1996 6627 6630
24. A.R. Gangloff, J. Litvak, E.J. Shelton, D. Sperandio, V.R. Wang, and K.D. Rice Tetrahedron Lett. 42 2001 1441 1443
25. V.N. Yarovenko, I.V. Zavarzin, and M.M. Krayushkin Russ. Chem. Bull. 35 1986 1106
26. J.K. Augustine, V. Akabote, S.G. Hegde, and P. Alagarsamy J. Org. Chem. 74 2009 5640 5643
27. S. Buscemi, A. Pace, and N. Vivona Tetrahedron Lett. 41 2000 7977 7981
28. Y.X. Zhang, K. Sasaki, and T. Hirota J. Heterocycl. Chem. 36 1999 787 791
29. J. Suwiński, K. Świerczek, P. Wagner, M. Kubicki, T. Borowiak, and J. Słowikowska J. Heterocycl. Chem. 40 2003 523 528
30. F.B. Bordwell Acc. Chem. Res. 21 1988 456 463
31. I.M. Kolthoff, M.K. Chantooni Jr., and S. Bhowmik J. Am. Chem. Soc. 90 1968 23 28
32. R. Grigg Tetrahedron: Asymmetry 6 1995 2475 2486