Synthesis of isoindolinones by palladium-catalyzed carbonylative cyclization of 2-bromobenzaldehyde with diamines

Synthetic Communications

Volumn 28, Issue 5, 1998, Pages 849-857

  Cho, C S ^a   Jiang, L H ^a   Shim, S C ^a  

^a Kyungpook National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDEHYDE DERIVATIVE; CARBON MONOXIDE; DIAMINE; ISOINDOLE DERIVATIVE; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; SYNTHESIS;

EID: 0031929221     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00032719808006483     Document Type: Article

References (17)

1. For recent reviews, see: (a) Tamaru, Y. and Yoshida, Z. J. Organomet. Chem. 1987, 334, 213. (b) Sakamoto, T., Kondo, Y. and Yamanaka, H. Heterocycles 1988, 27, 2225. (c) Hegedus, L.S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113. (d) Hegedus, L.S. "Transition Metals in the Synthesis of Complex Organic Molecules," University Science Book, California, 1994. (e) Thebtaranonth, C. and Thebtaranonth, Y. "Cyclization Reaction," CRC Press, London, 1994. (f) Tsuji, J. "Palladium Reagents and Catalysts," Wiley, Chichester, 1995. (g) Negishi, E., Coperet, C., Ma, S., Lee, S.-Y. and Lui, F. Chem. Rev. 1996, 96, 365.
2. For recent reviews, see: (a) Tamaru, Y. and Yoshida, Z. J. Organomet. Chem. 1987, 334, 213. (b) Sakamoto, T., Kondo, Y. and Yamanaka, H. Heterocycles 1988, 27, 2225. (c) Hegedus, L.S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113. (d) Hegedus, L.S. "Transition Metals in the Synthesis of Complex Organic Molecules," University Science Book, California, 1994. (e) Thebtaranonth, C. and Thebtaranonth, Y. "Cyclization Reaction," CRC Press, London, 1994. (f) Tsuji, J. "Palladium Reagents and Catalysts," Wiley, Chichester, 1995. (g) Negishi, E., Coperet, C., Ma, S., Lee, S.-Y. and Lui, F. Chem. Rev. 1996, 96, 365.
3. For recent reviews, see: (a) Tamaru, Y. and Yoshida, Z. J. Organomet. Chem. 1987, 334, 213. (b) Sakamoto, T., Kondo, Y. and Yamanaka, H. Heterocycles 1988, 27, 2225. (c) Hegedus, L.S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113. (d) Hegedus, L.S. "Transition Metals in the Synthesis of Complex Organic Molecules," University Science Book, California, 1994. (e) Thebtaranonth, C. and Thebtaranonth, Y. "Cyclization Reaction," CRC Press, London, 1994. (f) Tsuji, J. "Palladium Reagents and Catalysts," Wiley, Chichester, 1995. (g) Negishi, E., Coperet, C., Ma, S., Lee, S.-Y. and Lui, F. Chem. Rev. 1996, 96, 365.
4. For recent reviews, see: (a) Tamaru, Y. and Yoshida, Z. J. Organomet. Chem. 1987, 334, 213. (b) Sakamoto, T., Kondo, Y. and Yamanaka, H. Heterocycles 1988, 27, 2225. (c) Hegedus, L.S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113. (d) Hegedus, L.S. "Transition Metals in the Synthesis of Complex Organic Molecules," University Science Book, California, 1994. (e) Thebtaranonth, C. and Thebtaranonth, Y. "Cyclization Reaction," CRC Press, London, 1994. (f) Tsuji, J. "Palladium Reagents and Catalysts," Wiley, Chichester, 1995. (g) Negishi, E., Coperet, C., Ma, S., Lee, S.-Y. and Lui, F. Chem. Rev. 1996, 96, 365.
5. For recent reviews, see: (a) Tamaru, Y. and Yoshida, Z. J. Organomet. Chem. 1987, 334, 213. (b) Sakamoto, T., Kondo, Y. and Yamanaka, H. Heterocycles 1988, 27, 2225. (c) Hegedus, L.S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113. (d) Hegedus, L.S. "Transition Metals in the Synthesis of Complex Organic Molecules," University Science Book, California, 1994. (e) Thebtaranonth, C. and Thebtaranonth, Y. "Cyclization Reaction," CRC Press, London, 1994. (f) Tsuji, J. "Palladium Reagents and Catalysts," Wiley, Chichester, 1995. (g) Negishi, E., Coperet, C., Ma, S., Lee, S.-Y. and Lui, F. Chem. Rev. 1996, 96, 365.
6. For recent reviews, see: (a) Tamaru, Y. and Yoshida, Z. J. Organomet. Chem. 1987, 334, 213. (b) Sakamoto, T., Kondo, Y. and Yamanaka, H. Heterocycles 1988, 27, 2225. (c) Hegedus, L.S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113. (d) Hegedus, L.S. "Transition Metals in the Synthesis of Complex Organic Molecules," University Science Book, California, 1994. (e) Thebtaranonth, C. and Thebtaranonth, Y. "Cyclization Reaction," CRC Press, London, 1994. (f) Tsuji, J. "Palladium Reagents and Catalysts," Wiley, Chichester, 1995. (g) Negishi, E., Coperet, C., Ma, S., Lee, S.-Y. and Lui, F. Chem. Rev. 1996, 96, 365.
7. For recent reviews, see: (a) Tamaru, Y. and Yoshida, Z. J. Organomet. Chem. 1987, 334, 213. (b) Sakamoto, T., Kondo, Y. and Yamanaka, H. Heterocycles 1988, 27, 2225. (c) Hegedus, L.S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113. (d) Hegedus, L.S. "Transition Metals in the Synthesis of Complex Organic Molecules," University Science Book, California, 1994. (e) Thebtaranonth, C. and Thebtaranonth, Y. "Cyclization Reaction," CRC Press, London, 1994. (f) Tsuji, J. "Palladium Reagents and Catalysts," Wiley, Chichester, 1995. (g) Negishi, E., Coperet, C., Ma, S., Lee, S.-Y. and Lui, F. Chem. Rev. 1996, 96, 365.
8. For the synthesis of isoindolinones via transition metal-catalyzed carbonylative cyclizations: (a) Bird, C.W. J. Organomet. Chem. 1973, 47, 296. (b) Thompson, J.M. and Heck, R.F. J. Org. Chem. 1975, 40, 2667. (c) Mori, M., Chiba, K. and Ban Y. J. Org. Chem. 1978, 43, 1684. (d) Brunet, J.J., Sidot, C. and Caubere, P. J. Org. Chem. 1983, 48, 1166. (e) Shim, S.C., Jiang, L.H., Lee, D.Y. and Cho, C.S. Bull. Korean Chem. Soc. 1995, 16, 1064.
9. For the synthesis of isoindolinones via transition metal-catalyzed carbonylative cyclizations: (a) Bird, C.W. J. Organomet. Chem. 1973, 47, 296. (b) Thompson, J.M. and Heck, R.F. J. Org. Chem. 1975, 40, 2667. (c) Mori, M., Chiba, K. and Ban Y. J. Org. Chem. 1978, 43, 1684. (d) Brunet, J.J., Sidot, C. and Caubere, P. J. Org. Chem. 1983, 48, 1166. (e) Shim, S.C., Jiang, L.H., Lee, D.Y. and Cho, C.S. Bull. Korean Chem. Soc. 1995, 16, 1064.
10. For the synthesis of isoindolinones via transition metal-catalyzed carbonylative cyclizations: (a) Bird, C.W. J. Organomet. Chem. 1973, 47, 296. (b) Thompson, J.M. and Heck, R.F. J. Org. Chem. 1975, 40, 2667. (c) Mori, M., Chiba, K. and Ban Y. J. Org. Chem. 1978, 43, 1684. (d) Brunet, J.J., Sidot, C. and Caubere, P. J. Org. Chem. 1983, 48, 1166. (e) Shim, S.C., Jiang, L.H., Lee, D.Y. and Cho, C.S. Bull. Korean Chem. Soc. 1995, 16, 1064.
11. For the synthesis of isoindolinones via transition metal-catalyzed carbonylative cyclizations: (a) Bird, C.W. J. Organomet. Chem. 1973, 47, 296. (b) Thompson, J.M. and Heck, R.F. J. Org. Chem. 1975, 40, 2667. (c) Mori, M., Chiba, K. and Ban Y. J. Org. Chem. 1978, 43, 1684. (d) Brunet, J.J., Sidot, C. and Caubere, P. J. Org. Chem. 1983, 48, 1166. (e) Shim, S.C., Jiang, L.H., Lee, D.Y. and Cho, C.S. Bull. Korean Chem. Soc. 1995, 16, 1064.
12. For the synthesis of isoindolinones via transition metal-catalyzed carbonylative cyclizations: (a) Bird, C.W. J. Organomet. Chem. 1973, 47, 296. (b) Thompson, J.M. and Heck, R.F. J. Org. Chem. 1975, 40, 2667. (c) Mori, M., Chiba, K. and Ban Y. J. Org. Chem. 1978, 43, 1684. (d) Brunet, J.J., Sidot, C. and Caubere, P. J. Org. Chem. 1983, 48, 1166. (e) Shim, S.C., Jiang, L.H., Lee, D.Y. and Cho, C.S. Bull. Korean Chem. Soc. 1995, 16, 1064.
13. For broad biological activities of isoindolinones: Takahashi, I., Kawakami, T., Hirano, E., Yokota, H. and Kitajima, H. Synlett 1996, 353 and references cited therein.
14. Cho, C.S., Lee, J.W., Lee, D.Y., Shim, S.C. and Kim, T.J. J. Chem. Soc., Chem. Commun. 1996, 2115.
15. Cho, C.S., Jiang, L.H., Lee, D.Y. and Shim, S.C. Bull. Korean Chem. Soc. 1996, 17, 1095.
16. Cho, C.S., Jiang, L.H., Lee, D.Y., Shim, S.C., Lee, H.S. and Cho, S.-D. J. Heterocyclic Chem. in press.
17. Cho, C.S., Chu, D.Y., Lee, D.Y., Shim, S.C., Kim, T.J., Lim, W.T. and Heo, N.H. Synth. Commun. in press.