Synthesis of α-isocyano-α-alkyl(aryl)acetamides and their use in the multicomponent synthesis of 5-aminooxazole, pyrrolo[3,4-a]pyridin-5-one and 4,5,6,7-tetrahydrofuro[2,3-c]pyridine

Synthesis

Volumn , Issue 1, 2005, Pages 161-165

  Fayol, Aude ^a   Housseman, Christopher ^a   Sun, Xiaowen ^a   Janvier, Pierre ^a   Bienaymé, Hugues ^b   Zhu, Jieping ^a  

^a CNRS   (France)

^b Chrysalon   (France)

Author keywords

Domino process; Heterocycles; Isonitrile; Multicomponent reaction; Oxazole; Pyrrolopyridinone; Tetrahydrofuropyridine

Indexed keywords

ALKYLATION; AMINES; AMINO ACIDS; AROMATIC COMPOUNDS;

Α-ISOCYANO-Β-PHENYLPROPIONAMIDE 1; BIFUNCTIONAL COMPOUND; MULTICOMPONENT SYNTHESIS;

SYNTHESIS (CHEMICAL);

4,5,6,7 TETRAHYDROFURO[2,3 C]PYRIDINE; 5 AMINOOXAZOLE; ACETAMIDE DERIVATIVE; ALPHA 1 ISOCYANO ALPHA ACETAMIDE; ALPHA ISOCYANO BETA PHENYLPROPIONAMIDE; AMINO ACID; HETEROCYCLIC COMPOUND; PHENYLPROPIONIC ACID DERIVATIVE; PYRIDINE DERIVATIVE; PYRROLO[3,4 B]PYRIDIN 5 ONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; MULTICOMPONENT REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 12344293588     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831225     Document Type: Article

References (32)

1. For recent reviews, see: (a) Ikeda, S. I. Acc. Chem. Res. 2000, 33, 511. (b) Weber, L. Curr. Med. Chem. 2002, 9, 2085. (c) Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306. (d) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51. (e) Orru, R. V. A.; De Greef, M. Synthesis 2003, 1471. (f) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101. (g) Jacobi von Wangelin, A.; Neumann, H.; Gördes, D.; Klaus, S.; Strübing, D.; Beller, M. Chem.-Eur. J. 2003, 9, 4286. (h) Murakami, M. Angew. Chem. Int. Ed. 2003, 42, 718.
2. For recent reviews, see: (a) Ikeda, S. I. Acc. Chem. Res. 2000, 33, 511. (b) Weber, L. Curr. Med. Chem. 2002, 9, 2085. (c) Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306. (d) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51. (e) Orru, R. V. A.; De Greef, M. Synthesis 2003, 1471. (f) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101. (g) Jacobi von Wangelin, A.; Neumann, H.; Gördes, D.; Klaus, S.; Strübing, D.; Beller, M. Chem.-Eur. J. 2003, 9, 4286. (h) Murakami, M. Angew. Chem. Int. Ed. 2003, 42, 718.
3. For recent reviews, see: (a) Ikeda, S. I. Acc. Chem. Res. 2000, 33, 511. (b) Weber, L. Curr. Med. Chem. 2002, 9, 2085. (c) Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306. (d) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51. (e) Orru, R. V. A.; De Greef, M. Synthesis 2003, 1471. (f) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101. (g) Jacobi von Wangelin, A.; Neumann, H.; Gördes, D.; Klaus, S.; Strübing, D.; Beller, M. Chem.-Eur. J. 2003, 9, 4286. (h) Murakami, M. Angew. Chem. Int. Ed. 2003, 42, 718.
4. For recent reviews, see: (a) Ikeda, S. I. Acc. Chem. Res. 2000, 33, 511. (b) Weber, L. Curr. Med. Chem. 2002, 9, 2085. (c) Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306. (d) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51. (e) Orru, R. V. A.; De Greef, M. Synthesis 2003, 1471. (f) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101. (g) Jacobi von Wangelin, A.; Neumann, H.; Gördes, D.; Klaus, S.; Strübing, D.; Beller, M. Chem.-Eur. J. 2003, 9, 4286. (h) Murakami, M. Angew. Chem. Int. Ed. 2003, 42, 718.
5. For recent reviews, see: (a) Ikeda, S. I. Acc. Chem. Res. 2000, 33, 511. (b) Weber, L. Curr. Med. Chem. 2002, 9, 2085. (c) Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306. (d) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51. (e) Orru, R. V. A.; De Greef, M. Synthesis 2003, 1471. (f) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101. (g) Jacobi von Wangelin, A.; Neumann, H.; Gördes, D.; Klaus, S.; Strübing, D.; Beller, M. Chem.-Eur. J. 2003, 9, 4286. (h) Murakami, M. Angew. Chem. Int. Ed. 2003, 42, 718.
6. For recent reviews, see: (a) Ikeda, S. I. Acc. Chem. Res. 2000, 33, 511. (b) Weber, L. Curr. Med. Chem. 2002, 9, 2085. (c) Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306. (d) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51. (e) Orru, R. V. A.; De Greef, M. Synthesis 2003, 1471. (f) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101. (g) Jacobi von Wangelin, A.; Neumann, H.; Gördes, D.; Klaus, S.; Strübing, D.; Beller, M. Chem.-Eur. J. 2003, 9, 4286. (h) Murakami, M. Angew. Chem. Int. Ed. 2003, 42, 718.
7. For recent reviews, see: (a) Ikeda, S. I. Acc. Chem. Res. 2000, 33, 511. (b) Weber, L. Curr. Med. Chem. 2002, 9, 2085. (c) Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306. (d) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51. (e) Orru, R. V. A.; De Greef, M. Synthesis 2003, 1471. (f) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101. (g) Jacobi von Wangelin, A.; Neumann, H.; Gördes, D.; Klaus, S.; Strübing, D.; Beller, M. Chem.-Eur. J. 2003, 9, 4286. (h) Murakami, M. Angew. Chem. Int. Ed. 2003, 42, 718.
8. For recent reviews, see: (a) Ikeda, S. I. Acc. Chem. Res. 2000, 33, 511. (b) Weber, L. Curr. Med. Chem. 2002, 9, 2085. (c) Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306. (d) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51. (e) Orru, R. V. A.; De Greef, M. Synthesis 2003, 1471. (f) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101. (g) Jacobi von Wangelin, A.; Neumann, H.; Gördes, D.; Klaus, S.; Strübing, D.; Beller, M. Chem.-Eur. J. 2003, 9, 4286. (h) Murakami, M. Angew. Chem. Int. Ed. 2003, 42, 718.
9. (a) Zhu, J. Eur. J. Org. Chem. 2003, 1133.
10. (b) Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168.
11. (a) Hoppe, D. Angew. Chem., Int. Ed. Engl. 1974, 13, 789.
12. (b) Schöllkopf, U. Angew. Chem., Int. Ed. Engl. 1977, 16, 339.
13. Van Leusen, D.; Van Leusen, A. M. Org. React. 2001, 57, 417.
14. Marcaccini, S.; Torroba, T. Org. Prep. Proced. Int. 1993, 25, 141.
15. Sun, X.; Janvier, P.; Zhao, G.; Bienaymé, H.; Zhu, J. Org. Lett. 2001, 3, 877.
16. Janvier, P.; Sun, X.; Bienaymé, H.; Zhu, J. J. Am. Chem. Soc. 2002, 124, 2560.
17. Fayol, A.; Zhu, J. Org. Lett. 2004, 6, 115.
18. Zhao, G.; Bughin, C.; Bienaymé, H.; Zhu, J. Synlett 2003, 1153.
19. (a) Urban, R.; Marquarding, D.; Seidel, P.; Ugi, I.; Weinelt, A. Chem. Ber. 1977, 110, 2012.
20. (b) Nunami, K. I.; Suzuki, M.; Matsumoto, K.; Yoneda, N.; Takiguchi, K. Agric. Biol. Chem. 1984, 48, 1073.
21. (c) Mazurkiewicz, R. Synthesis 1992, 941.
22. (a) Suzuki, M.; Nunami, K. I.; Moriya, T.; Matsumoto, K.; Yoneda, N. J. Org. Chem. 1978, 43, 4933.
23. (b) Bon, R. S.; Hong, C.; Bouma, M. J.; Schmitz, R. F.; De Kanter, F. J. J.; Lutz, M.; Spek, A. L.; Orru, R. V. A. Org. Lett. 2003, 5, 3759.
24. (a) Kulkarni, B. A.; Ganesan, A. Tetrahedron Lett. 1999, 40, 5633.
25. (b) Sisko, J.; Kassick, A. J.; Mellinger, M.; Filan, J. J.; Allen, A.; Olsen, M. A. J. Org. Chem. 2000, 65, 1516; and references cited therein.
26. (a) Zhao, G.; Sun, X.; Bienaymé, H.; Zhu, J. J. Am. Chem. Soc. 2001, 123, 6700.
27. (b) González-Zamora, E.; Fayol, A.; Bois-Choussy, M.; Chiaroni, A.; Zhu, J. J. Chem. Soc., Chem. Commun. 2001, 1684.
28. (c) Gámez-Montaño, R.; Zhu, J. J. Chem. Soc., Chem. Commun. 2002, 2448.
29. (d) Fayol, A.; Zhu, J. Angew. Chem. Int. Ed. 2002, 41, 3633.
30. (e) Janvier, P.; Bienaymé, H.; Zhu, J. Angew. Chem. Int. Ed. 2002, 41, 4291.
31. (f) Gámez-Montano, R.; González-Zamora, E.; Potier, P.; Zhu, J. Tetrahedron 2002, 58, 6351.
32. (g) Janvier, P.; Bois-Choussy, M.; Bienaymé, H.; J, Angew. Chem. Int. Ed. 2003, 42, 811.