Highly Substituted Pyrrolidinones and Pyridones by 4-CR/2-CR Sequence

Organic Letters

Volumn 6, Issue 1, 2004, Pages 39-42

  Beck, Barbara ^a   Picard, Anne ^a   Herdtweck, Eberhardt ^b   Dömling, Alexander ^a  

^a Biovertis AG   (Germany)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; ALDEHYDE DERIVATIVE; AMINE; CYANIDE; GLYOXAL; PHOSPHONOACETIC ACID; PYRIDONE DERIVATIVE;

ARTICLE; RING CLOSING METATHESIS; SUBSTITUTION REACTION; WITTIG REACTION;

EID: 0742304186     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035787n     Document Type: Article

References (15)

1. For comprehensive reviews, see: Maccarchini, S.; Torroba, P. Org. Prep. Proc. Intl. 1993, 25, 141. Dömling, A.; Ugi, I. Angew. Chem., Intl. Ed. 2000, 39, 3168.
2. For comprehensive reviews, see: Maccarchini, S.; Torroba, P. Org. Prep. Proc. Intl. 1993, 25, 141. Dömling, A.; Ugi, I. Angew. Chem., Intl. Ed. 2000, 39, 3168.
3. Isocyano carboxylic acids as educts, e.g.: (a) Gockel, G.; Lüdke, Ugi, I. In Isonitrile Chemistry; Ugi, I. Ed.; Academic Press: New York, 1971; p 159. Bossio, R.; Marcaccini, S.; Paoli, P.; Pepino, R. Synthesis 1994, 672. Formyl(keto)carboxylic acids as educts, e.g.: (b) Gross, H.; Gloede, J.; Keitel, I.; Kunath, D. J. Prakt. Chem. 1968, 37, 192. Harriman, G. C. B. Tetrahedron Lett. 1997, 38, 5591. β-Amino acids and peptides as educts, e.g.: (c) Ugi, I. Angew. Chem., Int. Ed. Engl. 1982, 21, 810. Failli, A.; Immer, H.; Götz, M. Can. J. Chem. 1979, 57, 3257. Cyclic Schiff bases, e.g.: (d) Dömling, A.; Ugi, I. Angew. Chem., Intl. Ed. Engl. 1993, 32, 563. Dömling, A.; Ugi, I. Herdtweck, E. Acta Chem. Scand. 1998 52, 107. Unprotected isocyano amines with a primary or secondary amine are mostly unstable, but see, e.g., p-isocyano aniline: (f) New, R. G. A.; Sutton, L. S. J. Chem. Soc. 1932, 1415. Kim, M.; Euler, W. B.; Rosen, W. J. Org. Chem. 1997, 62, 3766. Protected isocyano amines are known and very useful compounds, e.g., in PNA synthesis: (g) Dömling, A. Nucleosides Nucleotides 1998, 17, 1667.
4. Isocyano carboxylic acids as educts, e.g.: (a) Gockel, G.; Lüdke, Ugi, I. In Isonitrile Chemistry; Ugi, I. Ed.; Academic Press: New York, 1971; p 159. Bossio, R.; Marcaccini, S.; Paoli, P.; Pepino, R. Synthesis 1994, 672. Formyl(keto)carboxylic acids as educts, e.g.: (b) Gross, H.; Gloede, J.; Keitel, I.; Kunath, D. J. Prakt. Chem. 1968, 37, 192. Harriman, G. C. B. Tetrahedron Lett. 1997, 38, 5591. β-Amino acids and peptides as educts, e.g.: (c) Ugi, I. Angew. Chem., Int. Ed. Engl. 1982, 21, 810. Failli, A.; Immer, H.; Götz, M. Can. J. Chem. 1979, 57, 3257. Cyclic Schiff bases, e.g.: (d) Dömling, A.; Ugi, I. Angew. Chem., Intl. Ed. Engl. 1993, 32, 563. Dömling, A.; Ugi, I. Herdtweck, E. Acta Chem. Scand. 1998 52, 107. Unprotected isocyano amines with a primary or secondary amine are mostly unstable, but see, e.g., p-isocyano aniline: (f) New, R. G. A.; Sutton, L. S. J. Chem. Soc. 1932, 1415. Kim, M.; Euler, W. B.; Rosen, W. J. Org. Chem. 1997, 62, 3766. Protected isocyano amines are known and very useful compounds, e.g., in PNA synthesis: (g) Dömling, A. Nucleosides Nucleotides 1998, 17, 1667.
5. Isocyano carboxylic acids as educts, e.g.: (a) Gockel, G.; Lüdke, Ugi, I. In Isonitrile Chemistry; Ugi, I. Ed.; Academic Press: New York, 1971; p 159. Bossio, R.; Marcaccini, S.; Paoli, P.; Pepino, R. Synthesis 1994, 672. Formyl(keto)carboxylic acids as educts, e.g.: (b) Gross, H.; Gloede, J.; Keitel, I.; Kunath, D. J. Prakt. Chem. 1968, 37, 192. Harriman, G. C. B. Tetrahedron Lett. 1997, 38, 5591. β-Amino acids and peptides as educts, e.g.: (c) Ugi, I. Angew. Chem., Int. Ed. Engl. 1982, 21, 810. Failli, A.; Immer, H.; Götz, M. Can. J. Chem. 1979, 57, 3257. Cyclic Schiff bases, e.g.: (d) Dömling, A.; Ugi, I. Angew. Chem., Intl. Ed. Engl. 1993, 32, 563. Dömling, A.; Ugi, I. Herdtweck, E. Acta Chem. Scand. 1998 52, 107. Unprotected isocyano amines with a primary or secondary amine are mostly unstable, but see, e.g., p-isocyano aniline: (f) New, R. G. A.; Sutton, L. S. J. Chem. Soc. 1932, 1415. Kim, M.; Euler, W. B.; Rosen, W. J. Org. Chem. 1997, 62, 3766. Protected isocyano amines are known and very useful compounds, e.g., in PNA synthesis: (g) Dömling, A. Nucleosides Nucleotides 1998, 17, 1667.
6. Isocyano carboxylic acids as educts, e.g.: (a) Gockel, G.; Lüdke, Ugi, I. In Isonitrile Chemistry; Ugi, I. Ed.; Academic Press: New York, 1971; p 159. Bossio, R.; Marcaccini, S.; Paoli, P.; Pepino, R. Synthesis 1994, 672. Formyl(keto)carboxylic acids as educts, e.g.: (b) Gross, H.; Gloede, J.; Keitel, I.; Kunath, D. J. Prakt. Chem. 1968, 37, 192. Harriman, G. C. B. Tetrahedron Lett. 1997, 38, 5591. β-Amino acids and peptides as educts, e.g.: (c) Ugi, I. Angew. Chem., Int. Ed. Engl. 1982, 21, 810. Failli, A.; Immer, H.; Götz, M. Can. J. Chem. 1979, 57, 3257. Cyclic Schiff bases, e.g.: (d) Dömling, A.; Ugi, I. Angew. Chem., Intl. Ed. Engl. 1993, 32, 563. Dömling, A.; Ugi, I. Herdtweck, E. Acta Chem. Scand. 1998 52, 107. Unprotected isocyano amines with a primary or secondary amine are mostly unstable, but see, e.g., p-isocyano aniline: (f) New, R. G. A.; Sutton, L. S. J. Chem. Soc. 1932, 1415. Kim, M.; Euler, W. B.; Rosen, W. J. Org. Chem. 1997, 62, 3766. Protected isocyano amines are known and very useful compounds, e.g., in PNA synthesis: (g) Dömling, A. Nucleosides Nucleotides 1998, 17, 1667.
7. Isocyano carboxylic acids as educts, e.g.: (a) Gockel, G.; Lüdke, Ugi, I. In Isonitrile Chemistry; Ugi, I. Ed.; Academic Press: New York, 1971; p 159. Bossio, R.; Marcaccini, S.; Paoli, P.; Pepino, R. Synthesis 1994, 672. Formyl(keto)carboxylic acids as educts, e.g.: (b) Gross, H.; Gloede, J.; Keitel, I.; Kunath, D. J. Prakt. Chem. 1968, 37, 192. Harriman, G. C. B. Tetrahedron Lett. 1997, 38, 5591. β-Amino acids and peptides as educts, e.g.: (c) Ugi, I. Angew. Chem., Int. Ed. Engl. 1982, 21, 810. Failli, A.; Immer, H.; Götz, M. Can. J. Chem. 1979, 57, 3257. Cyclic Schiff bases, e.g.: (d) Dömling, A.; Ugi, I. Angew. Chem., Intl. Ed. Engl. 1993, 32, 563. Dömling, A.; Ugi, I. Herdtweck, E. Acta Chem. Scand. 1998 52, 107. Unprotected isocyano amines with a primary or secondary amine are mostly unstable, but see, e.g., p-isocyano aniline: (f) New, R. G. A.; Sutton, L. S. J. Chem. Soc. 1932, 1415. Kim, M.; Euler, W. B.; Rosen, W. J. Org. Chem. 1997, 62, 3766. Protected isocyano amines are known and very useful compounds, e.g., in PNA synthesis: (g) Dömling, A. Nucleosides Nucleotides 1998, 17, 1667.
8. Isocyano carboxylic acids as educts, e.g.: (a) Gockel, G.; Lüdke, Ugi, I. In Isonitrile Chemistry; Ugi, I. Ed.; Academic Press: New York, 1971; p 159. Bossio, R.; Marcaccini, S.; Paoli, P.; Pepino, R. Synthesis 1994, 672. Formyl(keto)carboxylic acids as educts, e.g.: (b) Gross, H.; Gloede, J.; Keitel, I.; Kunath, D. J. Prakt. Chem. 1968, 37, 192. Harriman, G. C. B. Tetrahedron Lett. 1997, 38, 5591. β-Amino acids and peptides as educts, e.g.: (c) Ugi, I. Angew. Chem., Int. Ed. Engl. 1982, 21, 810. Failli, A.; Immer, H.; Götz, M. Can. J. Chem. 1979, 57, 3257. Cyclic Schiff bases, e.g.: (d) Dömling, A.; Ugi, I. Angew. Chem., Intl. Ed. Engl. 1993, 32, 563. Dömling, A.; Ugi, I. Herdtweck, E. Acta Chem. Scand. 1998 52, 107. Unprotected isocyano amines with a primary or secondary amine are mostly unstable, but see, e.g., p-isocyano aniline: (f) New, R. G. A.; Sutton, L. S. J. Chem. Soc. 1932, 1415. Kim, M.; Euler, W. B.; Rosen, W. J. Org. Chem. 1997, 62, 3766. Protected isocyano amines are known and very useful compounds, e.g., in PNA synthesis: (g) Dömling, A. Nucleosides Nucleotides 1998, 17, 1667.
9. Isocyano carboxylic acids as educts, e.g.: (a) Gockel, G.; Lüdke, Ugi, I. In Isonitrile Chemistry; Ugi, I. Ed.; Academic Press: New York, 1971; p 159. Bossio, R.; Marcaccini, S.; Paoli, P.; Pepino, R. Synthesis 1994, 672. Formyl(keto)carboxylic acids as educts, e.g.: (b) Gross, H.; Gloede, J.; Keitel, I.; Kunath, D. J. Prakt. Chem. 1968, 37, 192. Harriman, G. C. B. Tetrahedron Lett. 1997, 38, 5591. β-Amino acids and peptides as educts, e.g.: (c) Ugi, I. Angew. Chem., Int. Ed. Engl. 1982, 21, 810. Failli, A.; Immer, H.; Götz, M. Can. J. Chem. 1979, 57, 3257. Cyclic Schiff bases, e.g.: (d) Dömling, A.; Ugi, I. Angew. Chem., Intl. Ed. Engl. 1993, 32, 563. Dömling, A.; Ugi, I. Herdtweck, E. Acta Chem. Scand. 1998 52, 107. Unprotected isocyano amines with a primary or secondary amine are mostly unstable, but see, e.g., p-isocyano aniline: (f) New, R. G. A.; Sutton, L. S. J. Chem. Soc. 1932, 1415. Kim, M.; Euler, W. B.; Rosen, W. J. Org. Chem. 1997, 62, 3766. Protected isocyano amines are known and very useful compounds, e.g., in PNA synthesis: (g) Dömling, A. Nucleosides Nucleotides 1998, 17, 1667.
10. Isocyano carboxylic acids as educts, e.g.: (a) Gockel, G.; Lüdke, Ugi, I. In Isonitrile Chemistry; Ugi, I. Ed.; Academic Press: New York, 1971; p 159. Bossio, R.; Marcaccini, S.; Paoli, P.; Pepino, R. Synthesis 1994, 672. Formyl(keto)carboxylic acids as educts, e.g.: (b) Gross, H.; Gloede, J.; Keitel, I.; Kunath, D. J. Prakt. Chem. 1968, 37, 192. Harriman, G. C. B. Tetrahedron Lett. 1997, 38, 5591. β-Amino acids and peptides as educts, e.g.: (c) Ugi, I. Angew. Chem., Int. Ed. Engl. 1982, 21, 810. Failli, A.; Immer, H.; Götz, M. Can. J. Chem. 1979, 57, 3257. Cyclic Schiff bases, e.g.: (d) Dömling, A.; Ugi, I. Angew. Chem., Intl. Ed. Engl. 1993, 32, 563. Dömling, A.; Ugi, I. Herdtweck, E. Acta Chem. Scand. 1998 52, 107. Unprotected isocyano amines with a primary or secondary amine are mostly unstable, but see, e.g., p-isocyano aniline: (f) New, R. G. A.; Sutton, L. S. J. Chem. Soc. 1932, 1415. Kim, M.; Euler, W. B.; Rosen, W. J. Org. Chem. 1997, 62, 3766. Protected isocyano amines are known and very useful compounds, e.g., in PNA synthesis: (g) Dömling, A. Nucleosides Nucleotides 1998, 17, 1667.
11. Isocyano carboxylic acids as educts, e.g.: (a) Gockel, G.; Lüdke, Ugi, I. In Isonitrile Chemistry; Ugi, I. Ed.; Academic Press: New York, 1971; p 159. Bossio, R.; Marcaccini, S.; Paoli, P.; Pepino, R. Synthesis 1994, 672. Formyl(keto)carboxylic acids as educts, e.g.: (b) Gross, H.; Gloede, J.; Keitel, I.; Kunath, D. J. Prakt. Chem. 1968, 37, 192. Harriman, G. C. B. Tetrahedron Lett. 1997, 38, 5591. β-Amino acids and peptides as educts, e.g.: (c) Ugi, I. Angew. Chem., Int. Ed. Engl. 1982, 21, 810. Failli, A.; Immer, H.; Götz, M. Can. J. Chem. 1979, 57, 3257. Cyclic Schiff bases, e.g.: (d) Dömling, A.; Ugi, I. Angew. Chem., Intl. Ed. Engl. 1993, 32, 563. Dömling, A.; Ugi, I. Herdtweck, E. Acta Chem. Scand. 1998 52, 107. Unprotected isocyano amines with a primary or secondary amine are mostly unstable, but see, e.g., p-isocyano aniline: (f) New, R. G. A.; Sutton, L. S. J. Chem. Soc. 1932, 1415. Kim, M.; Euler, W. B.; Rosen, W. J. Org. Chem. 1997, 62, 3766. Protected isocyano amines are known and very useful compounds, e.g., in PNA synthesis: (g) Dömling, A. Nucleosides Nucleotides 1998, 17, 1667.
12. Isocyano carboxylic acids as educts, e.g.: (a) Gockel, G.; Lüdke, Ugi, I. In Isonitrile Chemistry; Ugi, I. Ed.; Academic Press: New York, 1971; p 159. Bossio, R.; Marcaccini, S.; Paoli, P.; Pepino, R. Synthesis 1994, 672. Formyl(keto)carboxylic acids as educts, e.g.: (b) Gross, H.; Gloede, J.; Keitel, I.; Kunath, D. J. Prakt. Chem. 1968, 37, 192. Harriman, G. C. B. Tetrahedron Lett. 1997, 38, 5591. β-Amino acids and peptides as educts, e.g.: (c) Ugi, I. Angew. Chem., Int. Ed. Engl. 1982, 21, 810. Failli, A.; Immer, H.; Götz, M. Can. J. Chem. 1979, 57, 3257. Cyclic Schiff bases, e.g.: (d) Dömling, A.; Ugi, I. Angew. Chem., Intl. Ed. Engl. 1993, 32, 563. Dömling, A.; Ugi, I. Herdtweck, E. Acta Chem. Scand. 1998 52, 107. Unprotected isocyano amines with a primary or secondary amine are mostly unstable, but see, e.g., p-isocyano aniline: (f) New, R. G. A.; Sutton, L. S. J. Chem. Soc. 1932, 1415. Kim, M.; Euler, W. B.; Rosen, W. J. Org. Chem. 1997, 62, 3766. Protected isocyano amines are known and very useful compounds, e.g., in PNA synthesis: (g) Dömling, A. Nucleosides Nucleotides 1998, 17, 1667.
13. Isocyano carboxylic acids as educts, e.g.: (a) Gockel, G.; Lüdke, Ugi, I. In Isonitrile Chemistry; Ugi, I. Ed.; Academic Press: New York, 1971; p 159. Bossio, R.; Marcaccini, S.; Paoli, P.; Pepino, R. Synthesis 1994, 672. Formyl(keto)carboxylic acids as educts, e.g.: (b) Gross, H.; Gloede, J.; Keitel, I.; Kunath, D. J. Prakt. Chem. 1968, 37, 192. Harriman, G. C. B. Tetrahedron Lett. 1997, 38, 5591. β-Amino acids and peptides as educts, e.g.: (c) Ugi, I. Angew. Chem., Int. Ed. Engl. 1982, 21, 810. Failli, A.; Immer, H.; Götz, M. Can. J. Chem. 1979, 57, 3257. Cyclic Schiff bases, e.g.: (d) Dömling, A.; Ugi, I. Angew. Chem., Intl. Ed. Engl. 1993, 32, 563. Dömling, A.; Ugi, I. Herdtweck, E. Acta Chem. Scand. 1998 52, 107. Unprotected isocyano amines with a primary or secondary amine are mostly unstable, but see, e.g., p-isocyano aniline: (f) New, R. G. A.; Sutton, L. S. J. Chem. Soc. 1932, 1415. Kim, M.; Euler, W. B.; Rosen, W. J. Org. Chem. 1997, 62, 3766. Protected isocyano amines are known and very useful compounds, e.g., in PNA synthesis: (g) Dömling, A. Nucleosides Nucleotides 1998, 17, 1667.
14. Beck, B.; Magnin-Lachaux, M.; Herdtweck E.; Dömling, A. Org. Lett. 2001, 3, 2875.
15. A versatile source of isocyanides: www.priaton.de