An unusual Me3SiI-promoted [4+2] annulation and reduction: An efficient approach to construct 4H-benzopyrans

Chemical Communications

Volumn 48, Issue 3, 2012, Pages 437-439

  Wang, Feijun ^a   Qu, Mingliang ^a   Chen, Feng ^a   Li, Li ^a   Shi, Min ^a,b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

4H BENZOPYRAN; BENZOPYRAN DERIVATIVE; CARBONYL DERIVATIVE; ETHER; SALICYLALDEHYDE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CYCLIZATION; SUBSTITUTION REACTION;

EID: 82955186884     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c1cc16028a     Document Type: Article

References (50)

1. S. Wawzonek, in Heterocyclic Compounds, ed. R. C. Elderfield, John Wiley & Sons, New York, 1951, vol. 2
2. L. Merlini, in Advances in Heterocyclic Chemistry, ed. A. R. Katritzky, Academic, New York, 1975, vol. 18
3. J. D. Hepworth, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky, Pergamon, New York, 1984, vol. 3
4. B. E. Evans, K. E. Rittle, M. G. Bock, R. M. DiPardo, R. M. Freidinger, W. L. Whittle, G. F. Lundell, D. F. Veber, P. S. Anderson, R. S. L. Chang, V. J. Lotti, D. J. Cerino, T. B. Chen, P. J. Kling, K. A. Kunkel, J. P. Springer, J. Hirshfield, J. Med. Chem., 1988:31, 2235
5. C. D. Duarte, E. J. Barreiro, C. A. M. Fraga, Mini-Rev. Med. Chem., 2007:7, 1108
6. L. Costantino, D. Barlocco, Curr. Med. Chem., 2005:13, 65
7. G. P. Ellis, Chromenes, Chromanones, and Chromones (Chemistry of Heterocyclic Compounds), Wiley, New York, 1977, vol. 31
8. S. M. Sethna, Chem. Rev., 1945:36, 1
9. J. A. Joule and K. Mills, Heterocyclic Chemistry, Blackwell Science, Oxford, UK, 4th edn, 2000
10. K. C. Nicolaou, J. A. Pfefferkorn, H. J. Mitchell, A. J. Roecker, S. Barluenga, G.-Q. Cao, R. L. Affleck, J. E. Lillig, J. Am. Chem. Soc., 2000:122, 9954
11. Y.-D. Gong, J. Seo, Y. S. Chon, J. Y. Hwang, J. Y. Park, S. Yoo, J. Comb. Chem., 2003:5, 577
12. Y. Gaoni, R. Mechoulam, J. Am. Chem. Soc., 1964:86, 1646
13. C. R. Lupica, A. C. Riegel, A. F. Hoffman, Br. J. Pharmacol., 2004:143, 227
14. N. Bai, K. He, M. Roller, B. Zheng, X. Chen, Z. Shao, T. Peng, Q. Zheng, J. Agric. Food Chem., 2008:56, 11668
15. M. Mondal, V. G. Puranik, N. P. Argade, J. Org. Chem., 2007:72, 2068
16. H. O. House, Modern Synthetic Reactions, ed. W. A. Benjamin, Benjamin/Cummings Publishing, Los Angles, CA, 2nd edn, 1972
17. A. Menzek, J. Chem. Educ., 2002:79, 700
18. M. Hudlicky, Reduction in Organic Chemistry, ACS Monograph 188, 2nd edn, 1996
19. J. March, Advanced Organic Chemistry, Wiley, New York, 4th edn, 1992, 1214
20. J. Seyden-Penne, Reductions by the Alumino- and Borohydrides in Organic Synthesis, Wiley-VCH, Weinheim, 1997, ch. 2
21. G. A. Olah, S. C. Narang, Tetrahedron, 1982:38, 2225
22. G. A. Olah, G. K. S. Prakach and R. Krishnamurtiy, Adv. Silicon Chem., ed. Gerald L. Larson, Jai Press, Inc., Greenwich, CT, 1991, vol. 1
23. T. Sakai, K. Miyata, S. Tsuboi, M. Utaka, Bull. Chem. Soc. Jpn., 1989:62, 4072
24. R. D. Miller, D. R. McKean, Synthesis, 1979, 730
25. H. H. Hergott, G. Simchen, Liebigs Ann. Chem., 1980, 1718
26. O. Babot, P. Cazeau, F. Duboudin, J. Organomet. Chem., 1987:326, C57
27. T. Pei, R. A. Widenhoefer, Chem. Commun., 2002, 650
28. H.-X. Wei, S. H. Kim, G. Li, Org. Lett., 2002:4, 3691
29. C. Timmons, A. Kattuboina, L. McPherson, J. Mills, G. Li, Tetrahedron, 2005:61, 11837
30. M. E. Jung, A. B. Mossman, M. A. Lyster, J. Org. Chem., 1978:43, 3698
31. K. C. Nicolaou, J. A. Pfefferkorn, A. J. Roecker, G.-Q. Cao, S. Barluenga, H. J. Mitchell, J. Am. Chem. Soc., 2000:122, 9939
32. D. A. Horton, G. T. Bourne, M. L. Smythe, Chem. Rev., 2003:103, 893
33. Y.-L. Shi, M. Shi, Org. Lett., 2005:7, 3057
34. G.-L. Zhao, Y.-L. Shi, M. Shi, Org. Lett., 2005:7, 4527
35. Y.-L. Shi, M. Shi, Chem.-Eur. J., 2006:12, 3374
36. Y.-W. Guo, Y.-L. Shi, H.-B. Li, M. Shi, Tetrahedron, 2006:62, 5875
37. M. Shi, X.-Y. Tang, Y.-H. Yang, Org. Lett., 2007:9, 4017
38. L.-Z. Dai, Y.-L. Shi, G.-L. Zhao, M. Shi, Chem.-Eur. J., 2007:13, 3701
39. M. Jiang, M. Shi, Org. Lett., 2010:12, 2606
40. Y.-W. Sun, X.-Y. Guan, M. Shi, Org. Lett., 2010:12, 5664
41. E. Knoevenagel, Chem. Ber., 1894:27, 2345
42. G. Marciniak, A. Delgado, G. Leelere, J. Velly, N. Decken, J. Schwartz, J. Med. Chem., 1989:32, 1402
43. Y. Liu, R. Zhang, C. He, D. Dang, C. Duan, Chem. Commun., 2010:46, 746
44. B. C. Ranu, R. Jana, Eur. J. Org. Chem., 2006, 3767
45. C. C. Malakar, D. Schmidt, J. Conrad, U. Beifuss, Org. Lett., 2011:13, 1972
46. Y. Fang, C. Li, J. Org. Chem., 2006:71, 6427
47. J. Fan, Z. Wang, Chem. Commun., 2008, 5381
48. K. D. Paull, R. H. Shoemaker, L. Hodes, A. Monks, D. A. Scudiero, L. Rubinstein, J. Plowman, M. R. Boyd, J. Natl. Cancer Inst., 1989:81, 1088
49. J. Z. Deng, D. J. Newman, S. M. Hecht, J. Nat. Prod., 2000:63, 1269
50. B. N. Zhou, J. M. Hoch, R. K. Johnson, M. R. Mattern, W. K. Eng, J. Ma, S. M. Hecht, D. J. Newman, D. G. I. Kingston, J. Nat. Prod., 2000:63, 1273