Radical annulations with nitriles: Novel cascade reactions of cyano- substituted alkyl and sulfanyl radicals with isonitriles

Tetrahedron

Volumn 54, Issue 21, 1998, Pages 5587-5598

  Camaggi, Carlo Maurizio ^a   Leardini, Rino ^a   Nanni, Daniele ^a   Zanardi, Giuseppe ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ISONITRILE DERIVATIVE;

ARTICLE; CYCLIZATION; ELECTRON TRANSPORT; PRIORITY JOURNAL; PROTEIN TRANSPORT; REACTION ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0032554907     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00230-0     Document Type: Article

References (48)

1. 1. Curran, D. P. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4; p. 779. Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. Ryu, I; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177.
2. 1. Curran, D. P. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4; p. 779. Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. Ryu, I; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177.
3. 1. Curran, D. P. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4; p. 779. Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. Ryu, I; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177.
4. 2. a) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1991, 113, 2127.
5. b) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863.
6. c) Curran, D. P.; Josien, H.; Ko, S.-B. Angew. Chem. Int. Ed. 1995, 34, 2683.
7. d) Curran, D. P.; Liu, H.; Josien, H.; Ko, S.-B. Tetrahedron 1996, 52, 11385.
8. 3. a) Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1984, 1320.
9. b) Leardini, R.; Tundo, A.; Zanardi, G.; Pedulli, G. F. Synthesis 1985, 107.
10. c) Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Perkin Trans. 1 1986, 1591.
11. d) Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. Gazz. Chim. Ital. 1989, 119, 637.
12. e) Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1989, 757.
13. f) Leardini, R.; Nanni, D.; Santori, M.; Zanardi, G. Tetrahedron 1992, 48, 3961.
14. g) Guidotti, S.; Leardini, R.; Nanni, D.; Pareschi, P.; Zanardi, G. Tetrahedron Lett. 1995, 36, 451.
15. h) Leardini, R.; McNab, H.; Nanni, D. Tetrahedron 1995, 51, 12143.
16. i) Nanni, D.; Pareschi, P.; Rizzoli, C.; Sgarabotto, P.; Tundo, A. Tetrahedron 1995, 51, 9045.
17. j) Nanni, D.; Pareschi, P.; Tundo, A. Tetrahedron Lett. 1996, 37, 9337.
18. 4. Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394. This paper also contains a comprehensive literature citation on the chemistry and spectroscopic properties of imidoyl radicals.
19. 5. a) McNab, H. J. Chem. Soc., Perkin Trans. 1 1984, 371.
20. b) McNab, H. J. Chem. Soc., Perkin Trans, 1 1984, 377.
21. c) McNab, H.; Smith, G. S. J. Chem. Soc., Perkin Trans. 1 1984, 381.
22. d) Hickson, C. L.; McNab, H. J. Chem. Soc., Perkin Trans, 1 1984, 1569.
23. 6. Hydrolysis of the isonitriles - in the reaction mixture or during column chromatography - should afford the corresponding formamides, which showed no tendency to hydrolyse further to amines under the reaction conditions or chromatographic work up. The only other by-products expected were the corresponding nitriles, since isonitriles are known to isomerise under various conditions (see: Casanova, J.; Werner, N. D.; Schuster, R. E. J. Org. Chem. 1966, 31, 3473. Wolber, E. K. A.; Schmittel, M.; Rüchardt, C. Chem. Ber. 1992, 725, 525). Actually, considerable amounts of nitriles were formed during the reactions. Of course, all of the reactions were carried out with isonitriles uncontaminated by any significant trace of amines.
24. 6. Hydrolysis of the isonitriles - in the reaction mixture or during column chromatography - should afford the corresponding formamides, which showed no tendency to hydrolyse further to amines under the reaction conditions or chromatographic work up. The only other by-products expected were the corresponding nitriles, since isonitriles are known to isomerise under various conditions (see: Casanova, J.; Werner, N. D.; Schuster, R. E. J. Org. Chem. 1966, 31, 3473. Wolber, E. K. A.; Schmittel, M.; Rüchardt, C. Chem. Ber. 1992, 725, 525). Actually, considerable amounts of nitriles were formed during the reactions. Of course, all of the reactions were carried out with isonitriles uncontaminated by any significant trace of amines.
25. 7. Compound 11 could also be trapped by the excess isonitrile to give polymeric products and tars, which were actually detected in the reaction mixtures. Evidence for the formation of 11 was not obtained, neither by NMR spectroscopy nor by GC-MS analysis of the reaction crude. On the other hand, these compounds are expected to be very easily hydrolysed, especially if R is a trimethyltin moiety.
26. 8. Curran, D. P.; Kim, D.; Liu, H. T.; Shen, W. J. Am. Chem. Soc. 1988, 110, 5900. Curran, D. P.; Shen, W. J. Am. Chem. Soc. 1993, 115, 6051.
27. 8. Curran, D. P.; Kim, D.; Liu, H. T.; Shen, W. J. Am. Chem. Soc. 1988, 110, 5900. Curran, D. P.; Shen, W. J. Am. Chem. Soc. 1993, 115, 6051.
28. 9. a) Saegusa, T.; Kobayashi, S.; Ito, Y. J. Org. Chem. 1970, 35, 2118.
29. b) Blum, P. M.; Roberts, B. P. J. Chem. Soc., Chem. Commun. 1976, 535.
30. c) Blum, P. M.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1978, 1313.
31. d) Bachi, M. D.; Balanov, A.; Bar-Ner N. J. Org. Chem. 1994, 59, 7752.
32. e) Bachi, M. D.; Melman, A. J. Org. Chem. 1995, 60, 6242.
33. 1H-NMR analysis of the reaction crude (see Experimental Section).
34. 1H-NMR analysis - seem to indicate an unexpected, selective addition of the sulfanyl radical to the 4-position of 28b. In our opinion, this outcome is worthy of further investigation: the results will be published elsewhere, together with the X-ray structure of 29b.
35. 12. We never succeeded in obtaining crystals of the reaction products suitable for X-ray crystallographic determinations.
36. 13. Leonard, N. J.; Goode, W. E. J. Am. Chem. Soc. 1950, 72, 5404.
37. 14. Booth, B. L.; Jibodu, K. O.; Proença, M. F. J. J. Chem. Soc., Perkin Trans, 1 1983, 1067.
38. 15. Ugi, I.; Fetzer, U.; Eholzer, U.; Knupfer, H.; Offermann, K. Angew. Chem. Int. Ed. 1965, 4, 472.
39. 16. Ugi, I.; Meyr, R. Chem. Ber. 1960, 93, 239.
40. 17. Ingold, C. K. J. Chem. Soc. 1924, 125, 97.
41. 18. Bauer, L.; Welsh, T. J. Org. Chem. 1961, 26, 1443.
42. 19. Johnston, T. P.; Gallagher, A. J. Org. Chem. 1963, 28, 1436.
43. 20. Beck, J. R.; Yahner, J. A. J. Org. Chem. 1978, 43, 1604.
44. 21. Murphy, S. T.; Taylor, W. C.; Vadasz, A. Aust. J. Chem. 1982, 35, 1215.
45. 22. Tilak, B. D.; Ravindranathan, T.; Subbaswami, K. N. Indian J. Chem. 1968, 6, 422.
46. 23. Zimmermann, J. Chem. Ber. 1880, 13, 1963.
47. 24. Haddadin, M. J.; Alkaysi, H. N.; Saheb, S. E. Tetrahedron 1970, 26, 1115.
48. 25. Bezdrik, A.; Friedländer, P.; Koeniger, P. Chem. Ber. 1908, 41, 227.