A new synthetic route to 2-oxazolines. The electrochemical reduction of N-(2,2-dichloroethyl)amides as a key step

Tetrahedron Letters

Volumn 39, Issue 9, 1998, Pages 1071-1074

  Guirado, Antonio ^a   Andreu, Raquel ^a   Gálvez, Jesús ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CONFORMATIONAL TRANSITION; ELECTROCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032567962     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10730-4     Document Type: Article

References (24)

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3. (c) Frump, J. A. Chem. Rev. 1971, 71, 483;
4. (d) Meyers, A.I.; Mihelich, E.D. Angew. Chem. Int. Ed. Engl. 1976, 15, 270;
5. (e) Reuman, M.; Meyers, A.I. Tetrahedron 1985, 41, 837;
6. (f) Maryanoff, B.E. in Oxazoles, Chemistry of Heterocyclic Compounds; Turchi, I. Ed.; Wiley: 1986; Vol. 45; p. 963;
7. (g) Gant, T.G.; Meyers, A.I. Tetrahedron 1994, 50, 2297.
8. 2. For example, (a) Vorbrüggen, H.; Krolikiewicz, K. Tetrahedron Lett. 1981, 22, 4471;
9. (b) Meyers, A.I.; Hoyer, D. 1985, 26, 4687;
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14. 3. For preceding papers see: Guirado, A.; Zapata, A.; Gálvez, J. Tetrahedron Lett. 1994, 35, 2365; Guirado, A.; Zapata, A.; Jones, P. G. Tetrahedron 1995, 51, 3641; Guirado, A; Zapata, A.; Jones, P.G. Tetrahedron 1995, 51, 10375.
15. 3. For preceding papers see: Guirado, A.; Zapata, A.; Gálvez, J. Tetrahedron Lett. 1994, 35, 2365; Guirado, A.; Zapata, A.; Jones, P. G. Tetrahedron 1995, 51, 3641; Guirado, A; Zapata, A.; Jones, P.G. Tetrahedron 1995, 51, 10375.
16. 3. For preceding papers see: Guirado, A.; Zapata, A.; Gálvez, J. Tetrahedron Lett. 1994, 35, 2365; Guirado, A.; Zapata, A.; Jones, P. G. Tetrahedron 1995, 51, 3641; Guirado, A; Zapata, A.; Jones, P.G. Tetrahedron 1995, 51, 10375.
17. 4. A free solvent reaction of chloral with amides provides chloralamides in nearly quantitative yields.
18. 5. Meldrum, A.N.; Bhojraj, M.G. J. Indian Chem. Soc. 1936, 13, 185.
19. 6. Shainyan, B.A.; Mirskova, A.N.; Kalikhman, I.D. Izv. Akad. USSR, Ser. Khim. 1976, 601; C.A. 85: 45932.
20. 7. Bal'on, Y.G.; Smirnov, V.A. Zh. Org. Khim. 1981, 17, 442; C.A. 95: 97299.
21. 8. For an extensive review about electrogeneration of bases see Utley, J.H.P. in Topics in Current Chemistry 142, Electrochemistry I, Steckhan, E. Ed.; Springer Verlag: Berlin, 1987; p. 131.
22. 9. See for example: Organic Electrochemistry; Lund, H.; Baizer, M.M. Eds.; Marcel Dekker, Inc.: New York, 1991; Chap. 8.
23. 13C n.m.r. spectra for crude and purified products were recorded showing negligible differences.
24. -1.