On the viability of 5-endo-dig cyclisations of O-propargylic hydroxylamine derivatives, leading to 2,5-dihydroisoxazoles (3-isoxazolines)

Tetrahedron Letters

Volumn 48, Issue 4, 2007, Pages 647-650

  Foot, Oliver F ^a   Knight, David W ^a   Low, Ai Cheng Lilian ^a   Li, YingFa ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 IODO 2,5 DIHYDROISOXAZOLE DERIVATIVE; HETEROCYCLIC COMPOUND; HYDROXYLAMINE; IODINE; ISOXAZOLE DERIVATIVE; ISOXAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 33845673741     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.114     Document Type: Article

References (44)

1. Baldwin J.E. J. Chem. Soc., Chem. Commun. (1976) 734-736 and 739-741
2. Fabrycy A., and Kubala J. Zh. Obshch. Khim. 31 (1961) 476-479
3. Fabrycy A., and Wichert Z. Zh. Obshch. Khim. 49 (1979) 2499-2504
4. Bew S.P., and Knight D.W. J. Chem. Soc., Chem. Commun. (1996) 1007-1008
5. For alternative approaches to the precursors 1, see:. El-Taeb G.M.M., Evans A.B., Jones S., and Knight D.W. Tetrahedron Lett. 41 (2000) 5945-5948
6. Knight D.W., Redfern A.L., and Gilmore J. J. Chem. Soc., Perkin Trans. 1 (2001) 2874-2883
7. Knight D.W., Redfern A.L., and Gilmore J. J. Chem. Soc., Perkin Trans. 1 (2002) 622-628
8. Rao M.S., Esho N., Sergeant C., and Dembinski R. J. Org. Chem. 68 (2003) 6788-6790
9. Sniady A., Wheeler K.A., and Dembinski R. Org. Lett. 7 (2005) 1769-1772
10. Yue D., Yao T., and Larock R.C. J. Org. Chem. 70 (2005) 10292-10296
11. Flynn B.L., Verdier-Pinard P., and Hamel E. Org. Lett. 3 (2001) 651-654
12. van Esseveldt B.C.J., Vervoort P.W.H., van Delft F.L., and Rutjes F.P.J.T. J. Org. Chem. 70 (2005) 1791-1795
13. Ramanathan B., Keith A.J., Armstrong D., and Odom A.L. Org. Lett. 6 (2004) 2957-2960
14. Knight D.W., and Sharland C.M. Synlett (2003) 2258-2260
15. Knight D.W., and Sharland C.M. Synlett (2004) 119-121
16. Yue D., and Larock R.C. Org. Lett. 6 (2004) 1037-1040
17. Amjad M., and Knight D.W. Tetrahedron Lett. 47 (2006) 2825-2828
18. Sromek A.W., Rubina M., and Gevorgyan V. J. Am. Chem. Soc. 127 (2005) 10500-10501 For a comprehensive listing, see Yao et al. cited in Ref. 6
19. Barluenga J., González J.M., Campos P.J., and Asensio G. Angew. Chem., Int. Ed. Engl. 27 (1988) 1546
20. Barluenga J., Trincado M., Marco-Arias M., Ballesteros A., Rubio E., and Gonzalez J.M. Chem. Commun. (2005) 2008-2010
21. Yao T., Campo M.A., and Larock R.C. J. Org. Chem. 70 (2005) 3511-3517
22. For recent applications, see:. Fuller A.A., Chen B., Minter A.R., and Mapp A.K. J. Am. Chem. Soc. 127 (2005) 5376-5383
23. Buhrlage S.J., Brennan B.B., Minter A.R., and Mapp A.K. J. Am. Chem. Soc. 127 (2005) 12456-12457 and references therein
24. For recent applications of nitrile oxide chemistry, see:. Lohse-Fraefel N., and Carreira E.M. Org. Lett. 7 (2005) 2011-2014 and references therein
25. Tiecco M., Testaferri L., Tingoli M., and Bagnoli L. J. Chem. Soc., Chem. Commun. (1995) 235-236
26. Aschwanden P., Frantz D.E., and Carreira E.M. Org. Lett. 2 (2000) 2331-2333
27. Bates R.W., and Sa-Ei K. Org. Lett. 4 (2002) 4225-4227
28. Janza B., and Studer A. Synthesis (2002) 2117-2123
29. Waldo J.P., and Larock R.C. Org. Lett. 7 (2005) 5203-5205
30. For reviews, see:. Mitsunobu O. Synthesis (1981) 1-28
31. Hughes D.L. Org. Prep. Proced. Int. 28 (1996) 127-164
32. Hughes D.L. Org. React. 42 (1992) 335-656
33. These methods have been highlighted in a recent review:. Dembinski R. Eur. J. Org. Chem. (2004) 2763-2772
34. Proctor A.J., Beautement K., Clough J.M., Knight D.W., and Li Y.-F. Tetrahedron Lett. 47 (2006) 5151-5154
35. Ing H.R., and Manske R.H.F. J. Chem. Soc. (1926) 2348-2351
36. Wolfe S., and Hasan S.K. Can. J. Chem. 48 (1970) 3572-3576
37. The main loss of material under the conditions shown in Scheme 3 appeared to be due to the formation of bis-tosyl derivatives. Subsequent experiments, performed after completion of the present project, have indicated that a superior method is to mix the reactants at -78 °C in dichloromethane and then allow the reaction mixture to slowly warm to ambient temperature during 3 h-Proctor, A. J., unpublished observations.
38. Full analytical and spectroscopic data consistent with the proposed structures have been obtained for all compounds reported herein.
39. For some Stille and Suzuki couplings of iodo-isoxazoles, see:. Labadie S.S. Synth. Commun. 24 (1994) 709-719
40. For various Heck and Sonogashira couplings of similar substrates, see:. Yamanaka H., Shiraiwa M., Yamamoto E., and Sakamoto T. Chem. Pharm. Bull. 29 (1981) 3543-3547
41. For palladium-catalysed couplings with phenylsulfonylacetonitrile, see:. Sakamoto T., Kondo Y., Suginome T., Ohba S., and Yamanaka H. Synthesis (1992) 552-554
42. For condensations of metallated derivatives with cyclic ketones, see:. Antequera T., Ramos V., and Vincente T. Heterocycles 24 (1986) 3203-3211
43. Polo C., Ramos V., Torroba T., Rodriguez M.L., Bossio R., Marcaccini S., and Pepino R. Heterocycles 32 (1991) 1757-1764
44. Li J.J., and Gribble G.W. Palladium in Heterocyclic Chemistry. Tetrahedron Organic Chemistry Series Vol. 20 (2000), Pergamon Press, Oxford