High pressure mediated three component Strecker synthesis of α-aminonitriles from ketones, aromatic amines and trimethylsilyl cyanide

Tetrahedron Letters

Volumn 43, Issue 50, 2002, Pages 9167-9169

  Matsumoto, Kiyoshi ^a   Kim, Jong Chul ^a   Hayashi, Naoto ^a   Jenner, Gérard ^b  

^a KYOTO UNIVERSITY   (Japan)

^b Polymers and Materials   (France)

Author keywords

aminonitriles; High pressure; Strecker reaction; Trimethylsilyl cyanide

Indexed keywords

AROMATIC AMINE; CYANIDE; KETONE DERIVATIVE; NITRILE; SOLVENT; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; PRESSURE; SOLUBILITY; STRECKER SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 0037049211     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02270-0     Document Type: Article

References (27)

1. For reviews of multicomponent reactions: Ugi, I.; Domling, A.; Ebert, B. Combinatorial Chem. 1999, 125; Ugi, I. Pure and Appl. Chem. 2001, 73, 187; Domling, A.; Ugi, I. Angew. Chem., Int. Ed. Engl. 2000, 39, 3168.
2. For reviews of multicomponent reactions: Ugi, I.; Domling, A.; Ebert, B. Combinatorial Chem. 1999, 125; Ugi, I. Pure and Appl. Chem. 2001, 73, 187; Domling, A.; Ugi, I. Angew. Chem., Int. Ed. Engl. 2000, 39, 3168.
3. For reviews of multicomponent reactions: Ugi, I.; Domling, A.; Ebert, B. Combinatorial Chem. 1999, 125; Ugi, I. Pure and Appl. Chem. 2001, 73, 187; Domling, A.; Ugi, I. Angew. Chem., Int. Ed. Engl. 2000, 39, 3168.
4. For examples of high pressured promoted multicomponent reactions: Mannich reaction; Matsumoto, K. Angew. Chem., Int. Ed. Engl. 1982, 21, 922; Matsumoto, K.; Uchida, T.; Hashimoto, S.; Iida, H.; Otani, S. Heterocycles 1993, 36, 2215. Ugi reaction; Yamada, T.; Yanagi, T.; Omote, Y.; Miyazawa, T.; Kuwata, S.; Sugiura, M.; Matsumoto, K. J. Chem. Soc., Chem. Commun. 1990, 1640. Passerini reaction; Yamada, T.; Motoyama, N.; Taniguchi, T.; Kazuta, Y.; Miyazawa, T.; Kuwata, S.; Matsumoto, K.; Sugiura, M. Chem. Lett. 1987, 723; Jenner, G. Tetrahedron Lett. 2002, 43, 1235. Domino-Horner-Wadsworth-Emmons-Michael reaction; Has-Becker, S.; Bodmann, K.; Kreuder, R.; Santoni, G.; Rein, T.; Reiser, O. Synlett 2001, 1395.
5. For examples of high pressured promoted multicomponent reactions: Mannich reaction; Matsumoto, K. Angew. Chem., Int. Ed. Engl. 1982, 21, 922; Matsumoto, K.; Uchida, T.; Hashimoto, S.; Iida, H.; Otani, S. Heterocycles 1993, 36, 2215. Ugi reaction; Yamada, T.; Yanagi, T.; Omote, Y.; Miyazawa, T.; Kuwata, S.; Sugiura, M.; Matsumoto, K. J. Chem. Soc., Chem. Commun. 1990, 1640. Passerini reaction; Yamada, T.; Motoyama, N.; Taniguchi, T.; Kazuta, Y.; Miyazawa, T.; Kuwata, S.; Matsumoto, K.; Sugiura, M. Chem. Lett. 1987, 723; Jenner, G. Tetrahedron Lett. 2002, 43, 1235. Domino-Horner-Wadsworth-Emmons-Michael reaction; Has-Becker, S.; Bodmann, K.; Kreuder, R.; Santoni, G.; Rein, T.; Reiser, O. Synlett 2001, 1395.
6. For examples of high pressured promoted multicomponent reactions: Mannich reaction; Matsumoto, K. Angew. Chem., Int. Ed. Engl. 1982, 21, 922; Matsumoto, K.; Uchida, T.; Hashimoto, S.; Iida, H.; Otani, S. Heterocycles 1993, 36, 2215. Ugi reaction; Yamada, T.; Yanagi, T.; Omote, Y.; Miyazawa, T.; Kuwata, S.; Sugiura, M.; Matsumoto, K. J. Chem. Soc., Chem. Commun. 1990, 1640. Passerini reaction; Yamada, T.; Motoyama, N.; Taniguchi, T.; Kazuta, Y.; Miyazawa, T.; Kuwata, S.; Matsumoto, K.; Sugiura, M. Chem. Lett. 1987, 723; Jenner, G. Tetrahedron Lett. 2002, 43, 1235. Domino-Horner-Wadsworth-Emmons-Michael reaction; Has-Becker, S.; Bodmann, K.; Kreuder, R.; Santoni, G.; Rein, T.; Reiser, O. Synlett 2001, 1395.
7. For examples of high pressured promoted multicomponent reactions: Mannich reaction; Matsumoto, K. Angew. Chem., Int. Ed. Engl. 1982, 21, 922; Matsumoto, K.; Uchida, T.; Hashimoto, S.; Iida, H.; Otani, S. Heterocycles 1993, 36, 2215. Ugi reaction; Yamada, T.; Yanagi, T.; Omote, Y.; Miyazawa, T.; Kuwata, S.; Sugiura, M.; Matsumoto, K. J. Chem. Soc., Chem. Commun. 1990, 1640. Passerini reaction; Yamada, T.; Motoyama, N.; Taniguchi, T.; Kazuta, Y.; Miyazawa, T.; Kuwata, S.; Matsumoto, K.; Sugiura, M. Chem. Lett. 1987, 723; Jenner, G. Tetrahedron Lett. 2002, 43, 1235. Domino-Horner-Wadsworth-Emmons-Michael reaction; Has-Becker, S.; Bodmann, K.; Kreuder, R.; Santoni, G.; Rein, T.; Reiser, O. Synlett 2001, 1395.
8. For examples of high pressured promoted multicomponent reactions: Mannich reaction; Matsumoto, K. Angew. Chem., Int. Ed. Engl. 1982, 21, 922; Matsumoto, K.; Uchida, T.; Hashimoto, S.; Iida, H.; Otani, S. Heterocycles 1993, 36, 2215. Ugi reaction; Yamada, T.; Yanagi, T.; Omote, Y.; Miyazawa, T.; Kuwata, S.; Sugiura, M.; Matsumoto, K. J. Chem. Soc., Chem. Commun. 1990, 1640. Passerini reaction; Yamada, T.; Motoyama, N.; Taniguchi, T.; Kazuta, Y.; Miyazawa, T.; Kuwata, S.; Matsumoto, K.; Sugiura, M. Chem. Lett. 1987, 723; Jenner, G. Tetrahedron Lett. 2002, 43, 1235. Domino-Horner-Wadsworth-Emmons-Michael reaction; Has-Becker, S.; Bodmann, K.; Kreuder, R.; Santoni, G.; Rein, T.; Reiser, O. Synlett 2001, 1395.
9. For examples of high pressured promoted multicomponent reactions: Mannich reaction; Matsumoto, K. Angew. Chem., Int. Ed. Engl. 1982, 21, 922; Matsumoto, K.; Uchida, T.; Hashimoto, S.; Iida, H.; Otani, S. Heterocycles 1993, 36, 2215. Ugi reaction; Yamada, T.; Yanagi, T.; Omote, Y.; Miyazawa, T.; Kuwata, S.; Sugiura, M.; Matsumoto, K. J. Chem. Soc., Chem. Commun. 1990, 1640. Passerini reaction; Yamada, T.; Motoyama, N.; Taniguchi, T.; Kazuta, Y.; Miyazawa, T.; Kuwata, S.; Matsumoto, K.; Sugiura, M. Chem. Lett. 1987, 723; Jenner, G. Tetrahedron Lett. 2002, 43, 1235. Domino-Horner-Wadsworth-Emmons-Michael reaction; Has-Becker, S.; Bodmann, K.; Kreuder, R.; Santoni, G.; Rein, T.; Reiser, O. Synlett 2001, 1395.
10. For a review, Duthaler, R. O. Tetrahedron 1994, 50, 1539.
11. For the most recent example: Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012 and references cited therein.
12. Strecker S. Liebigs Ann. Chem. 155:1870;177.
13. Shafran Y.M., Bakulev V.A., Mokrushin V.S. Russ. Chem. Rev. 1989;148.
14. Org. Synth. I, 21, 355; III, 66, 88, 225; IV, 274; V, 437.
15. Org. Synth. I, 21, 355; III, 66, 88, 225; IV, 274; V, 437.
16. Org. Synth. I, 21, 355; III, 66, 88, 225; IV, 274; V, 437.
17. Org. Synth. I, 21, 355; III, 66, 88, 225; IV, 274; V, 437.
18. Curini M., Epifano F., Marcotullio M.C., Rosati O., Rossi M. Synlett. 1999;315.
19. Typical procedure for the synthesis of 4: A mixture of ketone (3.0 mmol), aniline (3.0 mmol) and TMSCN (3.6 mmol) is diluted with toluene in a 4 ml Teflon capsule which is stored at 30°C for 24-48 h under high pressure. The mixture was cooled at 0°C and filtered. The solid was washed repeatedly with cyclohexane, and dried in vacuum. In the cases where the precipitates did not appear on cooling, the mixture was concentrated under reduced pressure, and the residue was chromatographed on silica gel.
20. In connection with this, no reaction of acetophenone with TMSCN without catalyst either at 0.1 and 300 MPa has been reported: Jenner, G. Tetrahedron Lett. 1999, 40, 491; see also, Choi, M. C.; Chen, S. S.; Matsumoto, K. Tetrahedron Lett. 1997, 38, 6669.
21. In connection with this, no reaction of acetophenone with TMSCN without catalyst either at 0.1 and 300 MPa has been reported: Jenner, G. Tetrahedron Lett. 1999, 40, 491; see also, Choi, M. C.; Chen, S. S.; Matsumoto, K. Tetrahedron Lett. 1997, 38, 6669.
22. High pressure apparatuses are now only moderately expensive, and can be employed, usefully and without much extra effort, in a much wider context than that originally envisaged. For examples of the reviews from our laboratories for organic reactions under high pressure: Jenner, G. Tetrahedron 2002, 58, 5185; Jenner, G. Tetrahedron 1997, 58, 5185; Matsumoto, K.; Acheson, R. M., Eds. Organic Reactions at High Pressures; New York: John Wiley & Sons, 1991; Ciobanu, M.: Matsumoto, K. Liebigs Ann./Recueil 1997, 623; Matsumoto, K.; Kaneko, M.; Katsura, H.; Hayashi, N.; Uchida, T.; Acheson, R. M. Heterocycles 1998, 47, 1135.
23. High pressure apparatuses are now only moderately expensive, and can be employed, usefully and without much extra effort, in a much wider context than that originally envisaged. For examples of the reviews from our laboratories for organic reactions under high pressure: Jenner, G. Tetrahedron 2002, 58, 5185; Jenner, G. Tetrahedron 1997, 58, 5185; Matsumoto, K.; Acheson, R. M., Eds. Organic Reactions at High Pressures; New York: John Wiley & Sons, 1991; Ciobanu, M.: Matsumoto, K. Liebigs Ann./Recueil 1997, 623; Matsumoto, K.; Kaneko, M.; Katsura, H.; Hayashi, N.; Uchida, T.; Acheson, R. M. Heterocycles 1998, 47, 1135.
24. High pressure apparatuses are now only moderately expensive, and can be employed, usefully and without much extra effort, in a much wider context than that originally envisaged. For examples of the reviews from our laboratories for organic reactions under high pressure: Jenner, G. Tetrahedron 2002, 58, 5185; Jenner, G. Tetrahedron 1997, 58, 5185; Matsumoto, K.; Acheson, R. M., Eds. Organic Reactions at High Pressures; New York: John Wiley & Sons, 1991; Ciobanu, M.: Matsumoto, K. Liebigs Ann./Recueil 1997, 623; Matsumoto, K.; Kaneko, M.; Katsura, H.; Hayashi, N.; Uchida, T.; Acheson, R. M. Heterocycles 1998, 47, 1135.
25. High pressure apparatuses are now only moderately expensive, and can be employed, usefully and without much extra effort, in a much wider context than that originally envisaged. For examples of the reviews from our laboratories for organic reactions under high pressure: Jenner, G. Tetrahedron 2002, 58, 5185; Jenner, G. Tetrahedron 1997, 58, 5185; Matsumoto, K.; Acheson, R. M., Eds. Organic Reactions at High Pressures; New York: John Wiley & Sons, 1991; Ciobanu, M.: Matsumoto, K. Liebigs Ann./Recueil 1997, 623; Matsumoto, K.; Kaneko, M.; Katsura, H.; Hayashi, N.; Uchida, T.; Acheson, R. M. Heterocycles 1998, 47, 1135.
26. High pressure apparatuses are now only moderately expensive, and can be employed, usefully and without much extra effort, in a much wider context than that originally envisaged. For examples of the reviews from our laboratories for organic reactions under high pressure: Jenner, G. Tetrahedron 2002, 58, 5185; Jenner, G. Tetrahedron 1997, 58, 5185; Matsumoto, K.; Acheson, R. M., Eds. Organic Reactions at High Pressures; New York: John Wiley & Sons, 1991; Ciobanu, M.: Matsumoto, K. Liebigs Ann./Recueil 1997, 623; Matsumoto, K.; Kaneko, M.; Katsura, H.; Hayashi, N.; Uchida, T.; Acheson, R. M. Heterocycles 1998, 47, 1135.
27. Recently, an intriguing method of high pressure (ca. 200 MPa) technology induced by water-freezing has been employed for Michael reaction: Hayashi, Y.; Nishimura, K. Chem. Lett. 2002, 296.