Vicarious Nucleophilic Substitution of (Chloroalkyl)oxazolines with Nitroarenes: Synthesis of (Nitrobenzyl)oxazolines

European Journal of Organic Chemistry

Volumn , Issue 20, 2003, Pages 4053-4058

  Florio, Saverio ^a   Lorusso, Patrizia ^b   Granito, Catia ^b   Ronzini, Ludovico ^b   Troisi, Luigino ^b  

^a UNIVERSITY OF BARI   (Italy)

^b UNIVERSITY OF SALENTO   (Italy)

Author keywords

Nucleophilic substitution; Synthesis design; Synthetic methods

Indexed keywords

(NITROBENZYL)OXAZOLINE DERIVATIVE; ALCOHOL DERIVATIVE; AROMATIC NITRO COMPOUND; CARBANION; CHLORINE DERIVATIVE; DIMETHYL SULFOXIDE; ION; OXAZOLINE DERIVATIVE; POTASSIUM DERIVATIVE; POTASSIUM TERT BUTOXIDE; UNCLASSIFIED DRUG; [(4 NITROPHENYL)OXAZOLINYL]ETHANOL;

ACIDITY; ARTICLE; CHEMICAL REACTION; ELECTRON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS; VICARIOUS NUCLEOPHILIC SUBSTITUTION REACTION;

EID: 0242291921     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300411     Document Type: Article

References (49)

1. [1a] J. Golinski, M. Makosza, Tetrahedron Lett. 1978, 37, 3495.
2. [1b] M. Makosza, J. Winiarski, Acc. Chem. Res. 1987, 20, 282.
3. [1c] M. Makosza, Pol. J. Chem. 1992, 66, 3.
4. [1d] M. Makosza, Z. Owczarczyk, J. Org. Chem. 1989, 54, 5094.
5. [1e] M. Makosza, Synthesis 1991, 103.
6. [1f] M. Makosza, E. Kwast, Tetrahedron 1995, 51, 8339.
7. [1g] M. Makosza, B. Chylinska, B. Mudryk, Liebigs Ann. Chem. 1984, 8.
8. [2a] M. Makosza, K. Sienkiewicz, J. Org. Chem. 1998, 63, 4199.
9. [2b] M. Makosza, K. Sienkiewicz, J. Org. Chem. 1990, 55, 4979.
10. [2c] T. Brose, F. Holtzscheiter, G. Mattersteig, W. Pritzkow, V. Voerckel, J. Pract. Chem. 1992, 334, 497.
11. [3a] M. Makosza, M. Bialecki, J. Org. Chem. 1992, 57, 4784.
12. [3b] M. Makosza, M. Bialecki, J. Org. Chem. 1998, 63, 4878.
13. [4a] A. R. Katritzky, K. L. Laurenzo, J. Org. Chem. 1988, 53, 3978.
14. [4b] A. R. Katritzky, K. L. Laurenzo, J. Org. Chem. 1986, 51, 5039.
15. [4c] P. F. Pagoria, R. Mitchell, R. D. Schmidt, J. Org. Chem. 1996, 61, 2934.
16. [4d] S. Seko, N. Kawamura, J. Org. Chem. 1996, 61, 442.
17. [5a] M. Makosza, K. Wojciechowski, Liebigs Ann./Recueil 1997, 1805.
18. [5b] M. Makosza, W. Danikiewicz, K. Wojciechowski, Phosphorus, Sulfur Silicon Relat. Elem. 1990, 53, 457.
19. [5c] E Terrier, Nucleophilic Aromatic Displacement: The Influence of the Nitro Group; VCH: New York, 1991.
20. [5d] O. N. Chupakin, V. N. Charushin, H. C. van der Plas, Nucleophilic Aromatic Substitution of Hydrogen; Academic Press: San Diego, 1994.
21. [6a] M. Makosza, T. Lemek, A. Kwast, F. Terrier, J. Org. Chem. 2002, 67, 394.
22. [6b] M. Makosza, A. Kwast, J. Phys. Org. Chem. 1998, 11, 341.
23. [6c] T. Glinka, M. Makosza, J. Org. Chem. 1983, 48, 3860.
24. [6d] S. Ostrowski, M. Makosza, Tetrahedron 1988, 44, 1721.
25. N. J. Lawrence, J. Liddle, D. A. Jackson, Tetrahedron Lett. 1995, 36, 8477.
26. M. Makosza, J. Golinski, J. Org. Chem. 1984, 49, 1488.
27. M. Makosza, J. Winiarski, J. Org. Chem. 1984, 49, 1494.
28. [10a] N. J. Liddle, L. Lawrence, S. M. Bushell, D. A. Jackson, J. Org. Chem. 2002, 67, 457.
29. Examples of the stepwise deprotonation and alkylation of VNS products, performed in two separate operations, have been reported: [10b] M. Makosza, A. Tyrala, Synth. Commun. 1986, 16, 419.
30. [10c] M. Makosza, W. Wojciechowski, K. Danikiewicz, Liebigs Ann. Chem. 1988, 203.
31. [10d] J. E. Macor, J. M. Wehner, Heterocycles 1993, 35, 349.
32. [10e] Z. Wrobel, M. Makosza, Tetrahedron 1997, 53, 5501.
33. [10f] J. E. Macor, J. M. Wehner, Tetrahedron Lett. 1991, 32, 7195.
34. [10g] Z. Wrobel, M. Makosza, Synlett 1993, 597.
35. [10h] M. Makosza, A. Tyrala, Acta Chem. Scand. 1992, 46, 689.
36. [10i] M. Makosza, J. Stalewski, Tetrahedron 1995, 51, 7263.
37. [10j] M. Makosza, J. Stalewski, O. Maslennikova, Synthesis 1997, 1131.
38. S. Florio, V. Capriati, R. Luisi, Tetrahedron Lett. 1996, 37, 4781.
39. S. Florio, V. Capriati, R. Luisi, L. Degennaro, C. Tralli, L. Troisi, Synthesis 2001, 15, 2299.
40. V Capriati, L. Degennaro, S. Florio, R. Luisi, Eur. J. Org. Chem. 2002, 17, 2961.
41. N. J. Lawrence, O. Lamarche, N. Thurrab, Chem. Commun. 1999, 689.
42. M. Makosza, M. Wenaell, M. Golinski, A. Kinowski, Bull. Pol. Acad. Sci. Chem. 1985, 33, 427.
43. [16a] J. F. Bunnett, R. E. Zahler, Chem. Rev. 1951, 49, 273.
44. [16b] J. Miller, Aromatic Nucleophilic Substitution; Elsevier: New York, 1968.
45. [16c] Th. J. De Boer, J. P. Dirks, in: Chemistry of the Nitro and Nitroso Group (Ed.: H. Feuer); Interscience: New York, 1969; chapter 8.
46. [16d] C. F. Bernasconi, Chimia 1980, 34, 1.
47. M. Prato, U. Quintily, L. Scapol, G. Scorrano, Bull. Soc. Chim. Fr. 1987, 99.
48. [18a] P. Breton, C. André-Barrès, Y. Langlois, Synth. Commun. 1992, 22, 2543.
49. [18b] M. J. Mintz, C. Walling, Organic Syntheses Collect. Vol. V, John Wiley & Sons: New York, 1973, p. 184.