Microwave-assisted Henry reaction: Solventless synthesis of conjugated nitroalkenes

Tetrahedron Letters

Volumn 38, Issue 29, 1997, Pages 5131-5134

  Vanna, Rajender S ^a,b   Dahiya, Rajender ^a,c   Kumar, Sudhir ^b  

^a SAM HOUSTON STATE UNIVERSITY   (United States)

^b HOUSTON ADVANCED RESEARCH CENTER   (United States)

^c Mukand Lal National College   (India)

Author keywords

[No Author keywords available]

Indexed keywords

NITROALKANE;

ARTICLE; CHEMICAL REACTION; MICROWAVE IRRADIATION; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0343907332     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01093-9     Document Type: Article

References (53)

1. (a) Varma, R. S.; Kabalka, G. W. Heterocycles 1986, 24, 2645;
2. (b) Barrett, A. G. M.; Graboski, G. G. Chem. Rev. 1986, 86, 751;
3. (c) Kabalka, G. W.; Varma, R. S. Org. Prep. Proc. Int. 1987, 19, 283;
4. (d) Kabalka, G. W.; Guindi, L. H. M.; Varma, R. S. Symposia-in-print Tetrahedron 1990, 46, 7443;
5. (e) Barrett, A. G. W. Chem. Soc. Rev. 1991, 20, 95.
6. Brown, A. W. A.; Robinson, D. B. W.; Hurtig, H.; Wenner, B. J. Can. J. Res. 1948, 26D, 177.
7. Bousquet, E. W.; Kirby, J. E.; Searle, N. E. U. S. Patent 2,335,384 1943; Chem. Abstr. 1944, 38, 2834.
8. Brian, P. W.; Grove, J. F.; McGowan, J. C. Nature 1946, 158, 876.
9. McGowan, J. C.; Brian, P. W.; Hemming, H. G. Ann. Appl. Biol. 1948, 35, 25.
10. Bocobo, F. C.; Curtis, A. C.; Block, W. D.; Harrell, E. R.; Evans, E. E.; Haines, R. F. Antibiol. Chemother. 1956, 6, 385.
11. Schales, O.; Graefe, H. A. J. Am. Chem. Soc. 1952, 74, 4486.
12. Dann, O.; Moller, E. F. Chem. Ber 1949, 82, 76.
13. Harker, R. J. U. S. Patent 2,889,246 1959; Chem. Abstr. 1959, 55, 17414i.
14. Zee-Cheng, K.; Cheng, C. J. Med. Chem. 1969, 12, 157.
15. (a) Bauer, H. H.; Urbas, L. The Chemistry of the Nitro and Nitroso Group, Feuer, H., Ed., Interscience, New York 1970, Part 2, pp 75-200;
16. (b) Seebach, D.; Colvin, E. W.; Lehar, F.; Weller, T. Chimia 1979, 31, 1;
17. (c) Schickh, O. V.; Apel, G.; Padeken, H. G.; Schwartz, H. H.; Segnitz, A. In Houben-Weyl: Methoden der Organische Chemie, Muller, E., Ed, George Thieme Verlag, Stuttgart 1971, 10/1, pp 9-462;
18. (d) Rajappa, S. Tetrahedron 1981, 37, 1453;
19. (e) For review of extensive Russian work on nitroalkene chemistry see: Perekalin, V. V. J. Org. Chem. USSR (Engl. Transl.) 1985, 27, 1011;
20. (f) Ballini, R.; Castagnani, R.; Petrini, M. J. Org. Chem. 1992, 57, 2160 and references cited therein.
21. Buckley, G. D.; Caife, C. W. J. Chem. Soc. 1947, 1471.
22. Ranganathan, D.; Rao, C. B.; Ranganathan, S.; Mehrotra, A.; Iyengar, R. J. Org. Chem. 1980, 45, 1185.
23. (a) Miyashita, M.; Yamaguchi, R.; Yoshikoshi, A. Chem. Lett. 1982, 1505;
24. (b) Melton, J.; Mc Murry, J. E. J. Org. Chem. 1975, 40, 2138.
25. Knochel, P.; Seebach, D. Synthesis 1982, 1017.
26. Knochel, P.; Seebach, D. Tetrahedron Lett. 1982, 23, 3897.
27. Seebach, D.; Knochel, P. Helv. Chim Acta 1984, 67, 261.
28. Karmarkar, S. N.; Kelkar, S. L.; Wadia, M. S. Synthesis 1985, 510.
29. Gairaud, C. B.; Lappin, G.R. J. Org. Chem. 1953, 18, 1.
30. (a) Varma, R. S.; Chatterjee, A. K.; Varma, M. Tetrahedron Lett. 1993, 34, 3207;
31. (b) Varma, R. S.; Chatterjee, A. K.; Varma, M. Tetrahedron Lett. 1993, 34, 4603;
32. (c) Varma, R. S.; Varma, M.; Chatterjee, A. K. J. Chem. Soc., Perkin. Trans. I 1993, 999;
33. (d) Varma, R. S.; Lamture, J. B.; Varma, M. Tetrahedron Lett. 1993, 34, 3029;
34. (e) Varma, R. S.; Dahiya, R.; Kumar, S. Tetrahedron Lett. 1997, 38, 2039;
35. (f) Varma, R. S.; Dahiya, R. Tetrahedron Lett. 1997, 38, 2043;
36. (g) Varma, R. S.; Saini, R. K. Tetrahedron Lett. 1997, 38, in press.
37. For recent reviews on microwave-assisted chemical reactions, see (a) Abramovich, R. A. Org. Prep. Proced. Int. 1991, 23, 683;
38. (b) Whittaker, A. G.; Mingos, D. M. P. J. Microwave Power Electromagn. Energy 1994, 29, 195;
39. (c) Majetich, G.; Hicks, R. J. Microwave Power Electromagn. Energy 1995, 30, 27;
40. (d) Caddick, S. Tetrahedron 1995, 51, 10403;
41. (e) For commentary on the First World Congress on Microwave Processing, see Dagani, D. Chem. Eng. News February 10,1997, 26.
42. (a) Giguere, R. J.; Namen, A. M.; Lopez, B. O.; Arepally, A.; Ramos, D. E.; Majetich, G.; Defauw, J. Tetrahedron Lett. 1987, 28, 6553 and references cited therein;
43. (b) Bose, A. K.; Manhas, M. S.; Ghosh, M.; Raju, V. S.; Tabei, K.; Urbanczyk-Lipkowska, Z. Heterocycles 1990, 30, 741;
44. (c) Bose, A. K.; Jayaraman, M.; Okawa, A.; Bari, S. S.; Robb, E. W.; Manhas, M. S. Tetrahedron Lett. 1996, 37, 6989 and references of this group cited therein.
45. (a) Bram, G.; Loupy, A.; Majdoub, M.; Gutierrez, E.; Ruiz-Hitzky, E. Tetrahedron 1990, 46, 5167;
46. (b) Marrero-Terrero, A. L.; Loupy, A. Synlett 1996, 245.
47. (a) Benalloum, A.; Labiad, B.; Villemin, D. J. Chem. Soc., Chem. Commun. 1989, 386;
48. (b) Villemin, D.; Labiad, B. Synth. Commun. 1990, 20, 3325 and 3333;
49. (c) Villemin, D.; Benalloum, A. Synth. Commun. 1991, 21, 1 and 63.
50. For a critical evaluation of activation process by microwaves see: Raner, K. D.; Strauss, C. R.; Vyskoc, F.; Mokbel, L. J. Org. Chem. 1993, 58, 950. The temperature of the reaction mixture inside the alumina bath (heat sink) in a Sears Kenmore microwave oven (2450 MHz) equipped with a turntable at its 40 % power level (full power level being 900 Watts) reached ∼90 °C after 2 minute of irradiation.
51. Trehan, I. R.; Bala, K.; Singh, J. B. Indian J. Chem. 1979, 18B, 295.
52. Koremura, M.; Oku, H.; Shono, T.; Nakanishi, T. Takamine Kenkyusho Nempo 1961, 13, 216.
53. Pulse sequence (2 min heating with 1 min interval) is needed only for the volatile nitroalkanes used.