One-pot regioselective synthesis of nitrophenyloxazolinyl styrene oxides by the Darzens reaction of vicarious nucleophilic substitution-formed carbanions of 2-dichloromethyl-4,4-dimethyloxazoline

Journal of Organic Chemistry

Volumn 69, Issue 15, 2004, Pages 4961-4965

  Florio, Saverio ^a,b   Lorusso, Patrizia ^c   Granito, Catia ^c   Luisi, Renzo ^a,b   Troisi, Luigino ^c  

^a UNIVERSITY OF BARI   (Italy)

^b CNR   (Italy)

^c UNIVERSITY OF SALENTO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; OXIDES; SOLVENTS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

DARZENS-LIKE REACTION; ELECTROPHILES;

STYRENE;

1,2 DIOXAZOLINYL 1,2 DINITROPHENYLETHENE; 2 DICHLOROMETHYL 4,4 DIMETHYLOXAZOLINE; ALDEHYDE; ANION; BENZYL DERIVATIVE; DICHLOROMETHYLOXAZOLINE; DIMETHYL SULFOXIDE; ETHYLENE DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; N,N DIMETHYLFORMAMIDE; NITROBENZENE; NITROPHENYLOXAZOLINYLOXIRANE DERIVATIVE; NITROPHENYLOXAZOLINYLSTYRENE OXIDE; OXAZOLINE DERIVATIVE; OXIDE; POTASSIUM DERIVATIVE; POTASSIUM TERT BUTOXIDE; SOLVENT; STYRENE DERIVATIVE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; DARZENS REACTION; ELECTRON; ROOM TEMPERATURE; SOLVENT EFFECT; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; WARMING;

EID: 3543031640     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0498359     Document Type: Article

References (34)

1. (a) Makosza, M.; Winiarski, J. Acc. Chem. Res. 1987, 20, 282-289.
2. (b) Makosza, M.; Wojciechowski, K. Liebig Ann. Chem. 1997, 1805.
3. (c) Kozhevnikov, D. N.; Rusinov, V. L.; Chupakhin, O. N.; Makosza, M.; Rykowski, A.; Wolinska, E. Eur. J. Org. Chem. 2002, 1412-1416.
4. (d) Donskaya, O. V.; Elokhina, V. N.; Nakhmanovich, A. S.; Vakul'skaya, T. I.; Larina, L. I.; Vokin, A. I.; Albanov, A. I.; Lopyrev, V. A. Tetrahedron Lett. 2002, 43, 6613-6616 and references cited therein.
5. (a) Terrier, F. Nucleophilic Aromatic Displacement: The Influence of the Nitro Group; VCH: New York, 1991.
6. (b) Chupakin, O. N.; Charushin, V. N.; van der Plas, H. C. Nucleophilic Aromatic Substitution of Hydrogen; Academic Press: San Diego, 1994.
7. (c) Makosza, M. Russ. Chem. Bull. 1996, 45, 491.
8. (d) Andujar Sanchez, C. M.; Iglesias, M. J.; Perez Alvarez, I. J.; Lopez Ortiz, F. Tetrahedron Lett. 2003, 44, 8441-8444.
9. (e) Rege, P. D.; Johnson, F. J. Org. Chem. 2003, 68, 6133-6139.
10. (f) King, T. J.; Nexal, C. E. J. Chem. Soc. 1962, 367.
11. (g) Gallardo, I.; Guirado, G.; Marquet, J. Chem. Eur. J. 2001, 7, 1759.
12. (h) Makosza, M.; Stalinski, K. Chem. Eur. J. 1997, 3, 2025.
13. (a) Florio, S.; Lorusso, P.; Granito, C.; Ronzini, L.; Troisi, L. Eur. J. Org. Chem. 2003, 4053-4058.
14. (b) Florio, S.; Lorusso, P.; Luisi, R.; Granito, C.; Ronzini, L.; Troisi, L. Eur. J. Org. Chem. 2004, 2118-2124.
15. (a) Lawrence, N. J.; Lamarche, O.; Thurrab, N. Chem. Commun. 1999, 689-690.
16. (b) Makosza, M.; Lemek, T.; Kwast, A.; Terrier, F. J. Org. Chem. 2002, 67, 394-400.
17. -5).
18. Lawrence, N. J.; Liddle, J.; Bushell, S. M.; Jackson, D. A. J. Org. Chem. 2002, 67, 457-464.
19. (a) Alvernhe, G.; Laurent, A. Bull. Soc. Chim. Fr. 1970, 8-9.
20. (b) Florio, S.; Capriati, V.; Di Martino, S.; Abbotto, A. Eur. J. Org. Chem. 1999, 409-418.
21. CCDC 234941 and 234942 contains the supplementary crystallographic data for compounds 8a and 11c, respectively. These data can be obtained free of charge at www.ccdc.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.; Fax: (int) +44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk.
22. Makosza, M.; Bialecki, M. Synlett 1991, 181. Makosza, M.; Sienkiewicz, K.; Wojciechowski, K. Synthesis 1990, 850. Makosza, M.; Owczarczyk, Z. J. Org. Chem. 1989, 54, 5094. Chen, B. C.; Chao, S. T.; Sundeen, J. E.; Tellew, J.; Ahmad, S. Tetrahedron Lett. 2002, 43, 1595.
23. Makosza, M.; Bialecki, M. Synlett 1991, 181. Makosza, M.; Sienkiewicz, K.; Wojciechowski, K. Synthesis 1990, 850. Makosza, M.; Owczarczyk, Z. J. Org. Chem. 1989, 54, 5094. Chen, B. C.; Chao, S. T.; Sundeen, J. E.; Tellew, J.; Ahmad, S. Tetrahedron Lett. 2002, 43, 1595.
24. Makosza, M.; Bialecki, M. Synlett 1991, 181. Makosza, M.; Sienkiewicz, K.; Wojciechowski, K. Synthesis 1990, 850. Makosza, M.; Owczarczyk, Z. J. Org. Chem. 1989, 54, 5094. Chen, B. C.; Chao, S. T.; Sundeen, J. E.; Tellew, J.; Ahmad, S. Tetrahedron Lett. 2002, 43, 1595.
25. Makosza, M.; Bialecki, M. Synlett 1991, 181. Makosza, M.; Sienkiewicz, K.; Wojciechowski, K. Synthesis 1990, 850. Makosza, M.; Owczarczyk, Z. J. Org. Chem. 1989, 54, 5094. Chen, B. C.; Chao, S. T.; Sundeen, J. E.; Tellew, J.; Ahmad, S. Tetrahedron Lett. 2002, 43, 1595.
26. (a) Makosza, M.; Golinski, J. J. Org. Chem. 1984, 49, 1488.
27. (b) Makosza, M.; Winiarski, J. J. Org. Chem. 1984, 49, 1494.
28. (a) Makosza, M.; Kwast, A. J. Phys. Org. Chem. 1998, 11, 341-349.
29. (b) Makosza, M.; Owczarczyk, Z. J. Org. Chem. 1989, 54, 5094-5100.
30. (c) Makosza, M.; Golinski, J.; Pankowski, J. Synthesis 1983, 40-42.
31. Makosza, M.; Glinka, T.; Kinowski, A. Tetrahedron 1984, 40, 1863-1868.
32. (a) Luisi, R.; Capriati, V.; Carlucci, C.; Degennaro, L.; Florio, S. Tetrahedron 2003, 59, 9707-9712.
33. (b) Capriati, V.; Florio, S.; Luisi, R.; Salomone, A. Org. Lett. 2002, 4, 2445-2448.
34. (c) Capriati, V.; Degennaro, L.; Favia, R.; Florio, S.; Luisi, R. Org. Lett. 2002, 4, 1551-1554.