Palladium-Catalyzed Synthesis of 3-(Alkylamino)isoindolin-1-ones by Carbonylative Cyclization of 2-Bromobenzaldehyde with Primary Amines

Journal of Heterocyclic Chemistry

Volumn 34, Issue 4, 1997, Pages 1371-1374

  Cho, Chan Sik ^d   Jiang, Li Hong ^d   Lee, Dong Yub ^d   Shim, Sang Chul ^a   Lee, Hyung Soo ^b   Cho, Sung Dong ^c  

^a Kyungpook National University   (South Korea)

^b Catholic University of Daegu   (South Korea)

^c Chosun University   (South Korea)

^d NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001316960     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570340446     Document Type: Article

References (21)

1. R. F. Heck, Palladium Reagents in Organic Syntheses, Academic Press, London, 1985, pp 341-400; H. M. Colquhoun, H. M. Tompson and M. V. Twigg, Carbonylation: Direct Synthesis of Carbonyl Compounds, Plenum Press; New York, 1991; M. Iwasald, Y. Ishii and M. Hidai, J. Synth. Org. Chem., Japan, 49, 909 (1991); C. Thebtaranonth and Y. Thebtaranonth, Cyclization Reaction, CRC Press, London, 1994, pp 255-330.
2. R. F. Heck, Palladium Reagents in Organic Syntheses, Academic Press, London, 1985, pp 341-400; H. M. Colquhoun, H. M. Tompson and M. V. Twigg, Carbonylation: Direct Synthesis of Carbonyl Compounds, Plenum Press; New York, 1991; M. Iwasald, Y. Ishii and M. Hidai, J. Synth. Org. Chem., Japan, 49, 909 (1991); C. Thebtaranonth and Y. Thebtaranonth, Cyclization Reaction, CRC Press, London, 1994, pp 255-330.
3. R. F. Heck, Palladium Reagents in Organic Syntheses, Academic Press, London, 1985, pp 341-400; H. M. Colquhoun, H. M. Tompson and M. V. Twigg, Carbonylation: Direct Synthesis of Carbonyl Compounds, Plenum Press; New York, 1991; M. Iwasald, Y. Ishii and M. Hidai, J. Synth. Org. Chem., Japan, 49, 909 (1991); C. Thebtaranonth and Y. Thebtaranonth, Cyclization Reaction, CRC Press, London, 1994, pp 255-330.
4. R. F. Heck, Palladium Reagents in Organic Syntheses, Academic Press, London, 1985, pp 341-400; H. M. Colquhoun, H. M. Tompson and M. V. Twigg, Carbonylation: Direct Synthesis of Carbonyl Compounds, Plenum Press; New York, 1991; M. Iwasald, Y. Ishii and M. Hidai, J. Synth. Org. Chem., Japan, 49, 909 (1991); C. Thebtaranonth and Y. Thebtaranonth, Cyclization Reaction, CRC Press, London, 1994, pp 255-330.
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10. For the synthesis of isoindolinones via transition metal-catalyzed carbonylative cyclization see: C. W. Bird, J. Organomet. Chem., 47, 296 (1973); J. M. Thompson and R. F. Heck, J. Org. Chem., 40, 2667 (1975); M. Mori, K. Chiba and Y. Ban, J. Org. Chem., 43, 1684 (1978); J. J. Brunet, C. Sidot and P. Caubere, J. Org. Chem., 48, 1166 (1983).
11. For the synthesis of isoindolinones via transition metal-catalyzed carbonylative cyclization see: C. W. Bird, J. Organomet. Chem., 47, 296 (1973); J. M. Thompson and R. F. Heck, J. Org. Chem., 40, 2667 (1975); M. Mori, K. Chiba and Y. Ban, J. Org. Chem., 43, 1684 (1978); J. J. Brunet, C. Sidot and P. Caubere, J. Org. Chem., 48, 1166 (1983).
12. For the synthesis of isoindolinones via transition metal-catalyzed carbonylative cyclization see: C. W. Bird, J. Organomet. Chem., 47, 296 (1973); J. M. Thompson and R. F. Heck, J. Org. Chem., 40, 2667 (1975); M. Mori, K. Chiba and Y. Ban, J. Org. Chem., 43, 1684 (1978); J. J. Brunet, C. Sidot and P. Caubere, J. Org. Chem., 48, 1166 (1983).
13. For the synthesis of isoindolinones via transition metal-catalyzed carbonylative cyclization see: C. W. Bird, J. Organomet. Chem., 47, 296 (1973); J. M. Thompson and R. F. Heck, J. Org. Chem., 40, 2667 (1975); M. Mori, K. Chiba and Y. Ban, J. Org. Chem., 43, 1684 (1978); J. J. Brunet, C. Sidot and P. Caubere, J. Org. Chem., 48, 1166 (1983).
14. C. S. Cho, J. W. Lee, D. Y. Lee, S. C Shim and T. J. Kim, J. Chem. Soc., Chem, Commun., 2115 (1996).
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16. S. C. Shim, D. Y. Lee, L. H. Jiang, T. J. Kim and S.-D. Cho, J. Heterocyclic Chem., 32, 363 (1995).
17. Based on 2-bromobenzaldehyde (1), the formation of 0.5 equivalent of 6 corresponds to 100% yield.
18. C. Coperet, T. Sugihara, G. Wu, I. Shimoyama and E. Negishi, J. Am. Chem. Soc., 117, 3422 (1995).
19. A. S. Guram, R. A. Rennels and S. L. Buchwald, Angew. Chem., Int. Ed. Engl., 34, 1348 (1995).
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