Natural Kaolinitic clay catalyzed conversion of nitriles to 2-oxazolines

Tetrahedron Letters

Volumn 39, Issue 5-6, 1998, Pages 459-462

  Jnaneshwara, G K ^a   Deshpande, V H ^a   Lalithambika, M ^b   Ravindranathan, T ^a   Bedekar, A V ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM SILICATE; NITRILE; OXAZOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CLAY; REACTION ANALYSIS;

EID: 0032576816     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10575-5     Document Type: Article

References (40)

1. 1. a) Frump, J.A. Chem. Rev. 1971, 71, 483.
2. b) Greene, T.W.; Wuts, P.G.M. Protecting Groups in Organic Synthesis, 2nd ed. J. wiley: New York, 1991.
3. c) Kocienski, P.J. Protecting Groups; Enders, D.; Noyori, R.; Trost, B.M., Eds.; George Thieme Verlag: Stuttgart, New York, 1994.
4. 2. a) Lutomski, K. A.; Meyers, A.I. In A symmetric Synthesis; Morisson, J.D., Ed.; Academic Press: Orlando FL, 1984; vol-3, p. 213.
5. b) Meyers, A.I. Acc. Chem. Res. 1978, 11, 375.
6. c) Meyers, A.I.; Mihclich, E.D. Angew. Chem. Int. Ed. Engl. 1976, 15, 270.
7. d) Reuman, M.; Meyers, A.I. Tetrahedron 1985, 41, 837.
8. e) Gant, T.G.; Meyers, A.I. Tetrahedron 1994, 50, 2297.
9. 3. a) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339.
10. b) Bolm, C. Angew. Chem. Int. Ed. Engl. 1991, 30, 542.
11. c) Pfaltz, A. Acta Chem. Scand. 1996, 50, 189.
12. 4. a) Lowenthal, R.E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005.
13. b) Evans, D.A.; Miller, S.J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460.
14. c) Bedekar, A.V.; Koroleva, E.B.; Andersson, P.G. J. Org. chem. 1997, 62, 2518.
15. d) Denmark, S.E.; Stavenger, R.A.; Faucher, A.-M.; Edwards, J.P. J. Org. Chem. 1997, 62, 3375 and references cited therein.
16. 5. a) Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
17. b) Nishiyama, H.; Park, S.-B.; Itoh, K. Chem. Lett. 1995, 599.
18. c) Evans, D.A.; Murry, J.A.; von Matt, P.; Norcross, R.D.; Miller, S.J. Angew. Chem. Int. Ed. Engl. 1995, 34, 798.
19. d) Evans, D.A.; Murry, J.A.; Kozlowski, M.C. J. Am. Chem. Soc. 1996, 118, 5814.
20. 6. Vorbruggen, H.; Krolikiewicz, K. Tetrahedron Lett. 1981, 22, 4471.
21. 7. a) Mller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
22. b) Corey, E.J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001.
23. 8. a) Bolm, C.; Weickhardt, K.; Zehnder, M.; Ranff, T. Chem. Ber. 1991, 124, 1173.
24. b) Clarke, D.S.; Wood, R. Synth. Commun. 1996, 26, 1335.
25. 9. Badiang, J.G.; Aube, J. J. Org. Chem. 1996, 61, 2484.
26. 10. a) Corey, E.J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807.
27. b) Wipf, P.; Miller, C.P. Tetrahedron Lett. 1992, 33, 907.
28. c) Lafargue, P.; Guenot, P.; Lellouche, J.-P. Heterocycles 1995, 41, 947.
29. d) Wipf, P.; Venkatraman, S. Tetrahedron Lett. 1996, 37, 4659.
30. 11. a) Laszlo, P. Science 1987, 255, 1473.
31. b) Laszlo, P. Pure & Appl. Chem. 1990, 62, 2027.
32. 12. Cornelis, A.; Laszlo, P. Synlett. 1994, 155.
33. 13. a) Sabu, K.R.; Sukumar, R.; Lalithambika, M. Bull. Chem. Soc. Jpn. 1993, 66, 3535.
34. b) Ponde, D.; Borate, H.B.; Sudalai, A.; Ravindranathan, T.; Deshpande, V.H. Tetrahedron Lett. 1996, 37, 4605.
35. c) Upadhya, T.T.; Daniel, T.; Sudalai, A.; Ravindranathan, T.; Sabu, K.R. Synth. commun. 1996, 26, 4539.
36. 14. The Kaolinitic clay was procured from the Padappakara mine of Quilon District, Kerala, India and was subsequently purified and characterised (ref. 13a).
37. 4 and concentrated. The residue was purified by column chromatography on nutral alumina to afford the oxazoline, 1, as oil (0.73 g; 86% yield) which was characterised by usual spectral methods. Method B: A solution of benzonitrile, 2-amino-2-methylpropanol (1.5 eq.), catalyst (20 % w/w) was refluxed in o-dichlorobenzene (180 °C) for 24 h and the product was isolated by direct chromalography to afford the oxazoline 1 (71 % yield).
38. 16. Brunner, H.; Obermann, U. Chem. Ber. 1989, 122, 499.
39. b) Brunner, H.; Obermann, U.; Wimmer, P. J. Organomet. chem. 1986, 316, C1.
40. c) Brunner, H.; Henrichs, C. Tetrahedron: Asymmetry 1995, 6, 653.