Microwave promoted rapid dehydration of aldoximes to nitriles on a solid support

Synthetic Communications

Volumn 27, Issue 8, 1997, Pages 1327-1333

  Kumar, H M Sampath ^a   Mohanty, Pradyumna K ^a   Kumar, M Suresh ^a   Yadav, J S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

NITRILE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MICROWAVE RADIATION; REACTION ANALYSIS; TECHNIQUE;

EID: 0001261252     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708006061     Document Type: Article

References (34)

1. (a) Friedrich, K. and Wallensfels, K. in The Chemistry of Cyanogroup; Rappoport, Z., Ed. Wiley-Interscience, New York, 1970.
2. (b) Mowry, D.T., Chem. Rev., 1948, 42, 250.
3. (a) Olah, G.A., Narang, S.C. and Garcia-Luna, A., Synthesis, 1980, 659.
4. (b) Olah, G.A., Vankar, Y.D. and Garcia-Luna, A., Synthesis, 1979, 227.
5. (c) Suzuki, H., Fuchita, T., Iwasa, A. and Mishina, T., Synthesis, 1978, 905.
6. (d) Kukhar, V.P. and Pasternak, V.L., Synthesis, 1974, 563.
7. (e) Pomeroy, J.H. and Craig, C.A., J.Am. Chem. Soc., 1959, 81, 6340.
8. (f) Foley, H.G. and Dalton, D.R., J. Chem. Soc., Chem. Commun., 1973, 628.
9. (g) Clive, D.L., J. Chem. Soc., Chem. Commun., 1970, 1014.
10. (h) Shimada, J., Ushigome, A. and Itbashi, K., J. Synth. Org. Chem., 1977, 35, 913.
11. (i) Olah, G,A, and Vanker, Y.D., Synthesis, 1978, 702
12. (j) Rosini, G., Baccolini, G. and Cacchi, S., J. Org. Chem., 1973, 38, 1060.
13. (k) Katritzky, A.R., Zyang, F.G. and Fan, W.Q., Org. Prep. Proceed Int., 1993, 25, 315.
14. Lehnert, W., Tetrahedron Lett., 1971, 6, 559.
15. Meshram, H.M., Synthesis, 1992, 943.
16. Narayan Rao, M., Kumar, P. and Garyali, K., Org. Prep. Proceed. Int., 1989, 21, 230.
17. Bandgar, B.P., Jagtap, S.R., Ghodeshwar, S.B. and Wadgaonkar, P.P., Synth. Commun., 1995, 25, (19) 2993.
18. (a) Mckillop, A. and Young, D.W., Synthesis, 1979, 481.
19. (b) Riego, J.M., Sedin, Z., Zaldivar, J.M., Marziazo, N.C. and Tortato, C., Tetrahedron Lett., 1996, 37, 513.
20. (a) Abramovitch, R.A. Org. Prep. Proceed. Int., 1991, 23, 683.
21. (b) Bose, A.K., Banik, B.K., Barakat, K.J. and Manhas, M.S., Synlett., 1993, 575.
22. (a) Ben Alloum, A., Labiad, B. and Villemin, D., J. Chem. Soc. Chem. Commun., 1989, 386.
23. (b) Gutierrez, E., Loupy, A., Bram, G. and Ruiz-Hitzky, E., Tetrahedron Lett., 1989, 30, 945.
24. (c) Veselosky, V.V., Gybin, A.S., Lozanova, A.V., Moiseenkov, A.M., Smit, W.A. and Caple, R., Tetrahedron Lett., 1988, 29, 175.
25. (d) Laszlo, P., Acc. Chem. Res., 1986, 19, 121.
26. (e) Villemin, D. and Ben Alloum, A., Synth. Commun., 1991, 21, 63.
27. (f) Villemin, D. and Ben Alloum, A., Synth. Commun., 1990, 20, 925.
28. (g) Villemin, D. and Labiad, B., Synth. Commun., 1990, 20, 3207.
29. (h) Villemin, D. and Labiad, B., Synth. Commun., 1990, 20, 3333.
30. Villemin, D., Lalaoui, M. and Ben Alloum, A., Chem. Ind. (London), 1991, 176.
31. th Ed., ELBS and Longmann, 1978.
32. Commercial sulfuric acid (99%, 5 ml) was stirred with a suspension of silica gel (Merck, mean particle size 10-40 μ) in acetone (50 ml) for 20 minutes. The catalyst obtained after filtration was dried (70°/20 torr, 1 hr) before use (58.6 g, free flowing powder).
33. (a) CRC Hand Book of Data on Organic Compounds : CRC Press, Boca Raton, Florida 1988,
34. rd ed. Chemical Rubber Company, Cleveland, Ohio, 1978.