One-pot multistep synthesis of 4-acetoxy-2-amino-3-arylbenzofurans from 1-aryl-2-nitroethylenes and cyclohexane-1,3-diones

Organic Letters

Volumn 7, Issue 7, 2005, Pages 1211-1214

  Ishikawa, Teruhiko ^a   Miyahara, Tadashi ^a   Asakura, Mami ^a   Higuchi, Shuichi ^a   Miyauchi, Yayoi ^a   Saito, Seiki ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; CYCLOHEXANE DERIVATIVE; ETHYLENE DERIVATIVE; TRIETHYLAMINE;

ARTICLE; CATALYSIS; CATALYST; REACTION ANALYSIS; SYNTHESIS;

EID: 17444402508     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047540b     Document Type: Article

References (31)

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7. For leading references, see: (a) Brady, W. T.; Giang, Y. F. J. Org. Chem. 1986, 51, 2145-2147. (b) Nicolaou, K. C.; Snyder, S. A.; Bigot, A.; Pfefferkon, J. A. Angew. Chem., Int. Ed. 2000, 39, 1093-1096; Angew. Chem. 2000, 112, 1135-1138. (c) Meshram, H. M.; Sekhar, K. C. Ganesh, Y. S. S. Yadav, J. S. Synlett 2000, 1273-1274. (d) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031-1032. (e) Katritzky, A. R.; Ji, Y.; Fang, Y.; Prakash, I. J. Org. Chem. 2001, 66, 5613-5615.
8. For leading references, see: (a) Brady, W. T.; Giang, Y. F. J. Org. Chem. 1986, 51, 2145-2147. (b) Nicolaou, K. C.; Snyder, S. A.; Bigot, A.; Pfefferkon, J. A. Angew. Chem., Int. Ed. 2000, 39, 1093-1096; Angew. Chem. 2000, 112, 1135-1138. (c) Meshram, H. M.; Sekhar, K. C. Ganesh, Y. S. S. Yadav, J. S. Synlett 2000, 1273-1274. (d) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031-1032. (e) Katritzky, A. R.; Ji, Y.; Fang, Y.; Prakash, I. J. Org. Chem. 2001, 66, 5613-5615.
9. For palladium-catalyzed synthesis of benzofurans from 2-alkynylphenol derivatives, see: (a) Larock, R. C.; Yum. E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, 3270-3271 and references therein. (b) Arcadi, A.; Cacchi, S.; Rosario, M. D.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280-9288. (c) Nan, Y.; Miao, H.; Yang, Z. Org. Lett. 2000, 2, 297-299. (d) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368.
10. For palladium-catalyzed synthesis of benzofurans from 2-alkynylphenol derivatives, see: (a) Larock, R. C.; Yum. E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, 3270-3271 and references therein. (b) Arcadi, A.; Cacchi, S.; Rosario, M. D.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280-9288. (c) Nan, Y.; Miao, H.; Yang, Z. Org. Lett. 2000, 2, 297-299. (d) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368.
11. For palladium-catalyzed synthesis of benzofurans from 2-alkynylphenol derivatives, see: (a) Larock, R. C.; Yum. E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, 3270-3271 and references therein. (b) Arcadi, A.; Cacchi, S.; Rosario, M. D.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280-9288. (c) Nan, Y.; Miao, H.; Yang, Z. Org. Lett. 2000, 2, 297-299. (d) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368.
12. For palladium-catalyzed synthesis of benzofurans from 2-alkynylphenol derivatives, see: (a) Larock, R. C.; Yum. E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, 3270-3271 and references therein. (b) Arcadi, A.; Cacchi, S.; Rosario, M. D.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280-9288. (c) Nan, Y.; Miao, H.; Yang, Z. Org. Lett. 2000, 2, 297-299. (d) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368.
13. Ishikawa, T.; Kadoya, R.; Arai, M.; Takahashi, H.; Kaisi, Y.; Mizuta, T.; Yoshikai, K.; Saito, S. J. Org. Chem. 2001, 66, 8000-8009.
14. For reviews of domino reactions, see: (a) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. 1993, 32, 131-163. (b) Waldmann, H. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995; p 193.
15. For reviews of domino reactions, see: (a) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. 1993, 32, 131-163. (b) Waldmann, H. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995; p 193.
16. For the preparation of trans-1-aryl-2-nitroethylenes (1), see Supporting Information.
17. Formation of cyclic oximes of this class was fragmentally reported; see: (a) Larson, H. O.; Oot, T.-C.; Sin, A. K. Q.; Hollenbeak, K. H.; Cue, F. L. Tetrahedron 1969, 25, 4005-4010. (b) Ansell, G. B.; Moore, D. W.; Nielsen, A. T. Chem. Commun. 1970, 1602-1603.
18. Formation of cyclic oximes of this class was fragmentally reported; see: (a) Larson, H. O.; Oot, T.-C.; Sin, A. K. Q.; Hollenbeak, K. H.; Cue, F. L. Tetrahedron 1969, 25, 4005-4010. (b) Ansell, G. B.; Moore, D. W.; Nielsen, A. T. Chem. Commun. 1970, 1602-1603.
19. For example, although the yield of 4e was 23%, the average yield per step can be calculated to be 85% if the process involves eight intermediates as shown in Scheme 3.
20. CCDC-251515 and -251516 contain the supplementary crystallographic data for this paper. These data can be obtained online free of charge (or from the Cambridge Crystallographic Data Center, 12, Union Road, Cambridge CB2 1EZ, UK; fax (+44) 1223-336-033; e-mail deposit@ccdc.cam.ac.uk). For similar information, see Supporting Information (CIF).
21. Among them, 2a-c are commercially available: for the synthesis of 2d, see ref 4.
22. For a 1,8-elimination reaction, see: Klaus, R.; Koenig, T. Tetrahedron Lett. 1985, 26, 4835-4838.
23. For benzofuran derivatives with an oxygen-linking substituent such as a alkoxycarbonyloxy group at C(2) and their synthetic implications, see: (a) Black, T. H.; Arrivo, S. M.; Schumm, J. S.; Knobeloch, J. M. J. Chem. Soc., Chem. Commun. 1986, 1524-1525. (b) Black, T. H.; Arrivo, S. M.; Schumm, J. S.; Knobeloch, J. M. J. Org. Chem. 1987, 52, 5425-5430. (c) Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4770-4773. (d) Hills, I. D.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 3921-3924. (e) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031-1032.
24. For benzofuran derivatives with an oxygen-linking substituent such as a alkoxycarbonyloxy group at C(2) and their synthetic implications, see: (a) Black, T. H.; Arrivo, S. M.; Schumm, J. S.; Knobeloch, J. M. J. Chem. Soc., Chem. Commun. 1986, 1524-1525. (b) Black, T. H.; Arrivo, S. M.; Schumm, J. S.; Knobeloch, J. M. J. Org. Chem. 1987, 52, 5425-5430. (c) Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4770-4773. (d) Hills, I. D.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 3921-3924. (e) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031-1032.
25. For benzofuran derivatives with an oxygen-linking substituent such as a alkoxycarbonyloxy group at C(2) and their synthetic implications, see: (a) Black, T. H.; Arrivo, S. M.; Schumm, J. S.; Knobeloch, J. M. J. Chem. Soc., Chem. Commun. 1986, 1524-1525. (b) Black, T. H.; Arrivo, S. M.; Schumm, J. S.; Knobeloch, J. M. J. Org. Chem. 1987, 52, 5425-5430. (c) Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4770-4773. (d) Hills, I. D.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 3921-3924. (e) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031-1032.
26. For benzofuran derivatives with an oxygen-linking substituent such as a alkoxycarbonyloxy group at C(2) and their synthetic implications, see: (a) Black, T. H.; Arrivo, S. M.; Schumm, J. S.; Knobeloch, J. M. J. Chem. Soc., Chem. Commun. 1986, 1524-1525. (b) Black, T. H.; Arrivo, S. M.; Schumm, J. S.; Knobeloch, J. M. J. Org. Chem. 1987, 52, 5425-5430. (c) Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4770-4773. (d) Hills, I. D.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 3921-3924. (e) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031-1032.
27. For benzofuran derivatives with an oxygen-linking substituent such as a alkoxycarbonyloxy group at C(2) and their synthetic implications, see: (a) Black, T. H.; Arrivo, S. M.; Schumm, J. S.; Knobeloch, J. M. J. Chem. Soc., Chem. Commun. 1986, 1524-1525. (b) Black, T. H.; Arrivo, S. M.; Schumm, J. S.; Knobeloch, J. M. J. Org. Chem. 1987, 52, 5425-5430. (c) Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4770-4773. (d) Hills, I. D.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 3921-3924. (e) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031-1032.
28. For example, see: (a) Mitchison, T. J. Chem. Biol. 1994, 1, 3-6. (b) Schreiber, S. L. Science 2000, 287, 1964-1969. (c) Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417-3421; Angew. Chem. 2001, 113, 3525-3529.
29. For example, see: (a) Mitchison, T. J. Chem. Biol. 1994, 1, 3-6. (b) Schreiber, S. L. Science 2000, 287, 1964-1969. (c) Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417-3421; Angew. Chem. 2001, 113, 3525-3529.
30. For example, see: (a) Mitchison, T. J. Chem. Biol. 1994, 1, 3-6. (b) Schreiber, S. L. Science 2000, 287, 1964-1969. (c) Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417-3421; Angew. Chem. 2001, 113, 3525-3529.
31. For example, see: (a) Mitchison, T. J. Chem. Biol. 1994, 1, 3-6. (b) Schreiber, S. L. Science 2000, 287, 1964-1969. (c) Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417-3421; Angew. Chem. 2001, 113, 3525-3529.