A novel reaction of the 'Huisgen zwitterion' with benzofuran-2,3-diones: An efficient strategy for the synthesis of spirocyclic benzofuran-2-one derivatives

Tetrahedron Letters

Volumn 54, Issue 40, 2013, Pages 5473-5476

  Wang, Ze Dong ^a   Dong, Nan ^a   Wang, Feng ^a   Li, Xin ^a   Cheng, Jin Pei ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Benzofuran 2,3 diones; Huisgen zwitterion; Spirocyclic benzofuran 2 ones

Indexed keywords

AMPHOLYTE; BENZOFURAN 2,3 DIONE DERIVATIVE; BENZOFURAN DERIVATIVE; NUCLEOPHILE; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; CRYSTAL STRUCTURE; MITSUNOBU REACTION; PURIFICATION; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 84883456135     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.07.129     Document Type: Article

References (54)

1. For review, see: K. Ding, Z. Han, and Z. Wang Chem. Asian J. 4 2009 32
2. For review, see: B.S. Kotha, C.A. Deb, and K. Lahiri Synthesis 2 2009 165
3. M. Sannigrahi Tetrahedron 55 1999 9007
4. For review, see: L. Hong, and R. Wang Adv. Synth. Catal. 255 2013 1023
5. G.S. Singh, and Z.Y. Desta Chem. Rev. 112 2012 6104
6. R. Rios Chem. Soc. Rev. 41 2012 1060
7. N.R. Ball-Jones, J.J. Badillo, and A.K. Franz Org. Biomol. Chem. 10 2012 5165
8. J.E.M.N. Klein, and R.J.K. Taylor Eur. J. Org. Chem. 2011 6821
9. F. Zhou, Y.-L. Liu, and J. Zhou Adv. Synth. Catal. 352 2010 1381
10. A.A. Esmaeili, and M. Nazer Synlett 2009 2119
11. A.A. Esmaeili, H. Vesalipour, R. Hosseinabadi, A.F. Zavareh, M.A. Naseri, and E. Ghiamati Tetrahedron Lett. 52 2011 4865
12. X. Li, F. Wang, N. Dong, and J.-P. Cheng Org. Biomol. Chem. 11 2013 1451
13. C. Cassani, X. Tian, E.C. Escudero-Adán, and P. Melchiorre Chem. Commun. 2011 233
14. M.B. Trost, N. Cramer, and S.M. Silverman J. Am. Chem. Soc. 129 2007 12396
15. G. Bergonzini, and P. Melchiorre Angew. Chem., Int. Ed. 51 2012 971
16. Y. Cao, X. Jiang, L. Liu, F. Shen, F. Zhang, and R. Wang Angew. Chem., Int. Ed. 50 2011 9124
17. K. Ohmatsu, M. Ito, T. Kunieda, and T. Ooi J. Am. Chem. Soc. 135 2013 590
18. X. Companyó, A. Zea, A.N.R. Alba, A. Mazzanti, A. Moyano, and R. Rios Chem. Commun. 2010 6953
19. F. Pesciaioli, X. Tian, G. Bencivenni, G. Bartoli, and P. Melchiorre Synlett 2010 1704
20. X.-F. Cheng, Y. Li, Y.-M. Su, F. Yin, J.-Y. Wang, J. Sheng, H.U. Vora, X.-S. Wang, and J.-Q. Yu J. Am. Chem. Soc. 135 2013 1236
21. M.W. Pertino, C. Theoduloz, J.A. Rodríguez, and V. Lazo J. Nat. Prod. 73 2010 639
22. B. Sontag, M. Ruth, P. Spiteller, N. Arnold, W. Steglich, M. Reichert, and G. Bringmann Eur. J. Org. Chem. 2006 1023
23. N. Nakatani, and R. Inatani Agric. Biol. Chem. 47 1983 353
24. C.H. Brieskorn, and A. Fuchs Chem. Ver. 95 1962 3034
25. H. Linde Helv. Chim. Acta 47 1964 1234
26. R. Huisgen J.I. Seeman, The Adventure Playground of Mechanisms and Novel Reactions: Profiles, Pathways and Dreams 1994 American Chemical Society Washington, DC 62
27. R. Huisgen, H. Blaschke, and E. Brunn Tetrahedron Lett. 7 1966 405
28. E. Brunn, and R. Huisgen Angew. Chem., Int. Ed. 8 1969 513
29. O. Mitsunobu Synthesis 1981 1
30. D.L. Hughes Org. Prep. Proced. Int. 28 1996 127
31. T. Watanabe, I.D. Gridnav, and T. Imamoto Chirality 12 2000 346
32. For review, see: O. Mitsunobu Synthesis 1981 1
33. For examples, see: D.L. Hughes Org. React. 42 1992 335
34. D. Camp, and I.D. Jenkins J. Org. Chem. 54 1989 3045
35. D. Camp, and I.D. Jenkins J. Org. Chem. 54 1989 3049
36. S.R. Wilson, J. Perez, and A. Pasternak J. Am. Chem. Soc. 115 1993 1994
37. D.L. Hughes, and R.A. Reamer J. Org. Chem. 61 1996 2967
38. T. Watanabe, I.D. Gridnev, and T. Imamoto Chirality 12 2000 346
39. C. Ahn, R. Correia, and P. DeShong J. Org. Chem. 67 2002 1751
40. J. McNulty, A. Capretta, V. Laritchev, J. Dyck, and A.J. Robertson Angew. Chem., Int. Ed. 42 2003 4051
41. C.J. Dinsmore, and S.P. Mercer Org. Lett. 6 2004 2885
42. R.D. Otte, T. Sakata, I.A. Guzei, and D. Lee Org. Lett. 7 2005 495
43. V. Nair, R.S. Menon, A.R. Sreekanth, N. Abhilash, and A.T. Biju Acc. Chem. Res. 39 2006 520
44. V. Nair, S.C. Mathew, A.T. Biju, and E. Suresh Angew. Chem., Int. Ed. 46 2007 2070
45. V. Nair, A.T. Biju, K. Mohanan, and E. Suresh Org. Lett. 8 2006 2213
46. V. Nair, A.T. Biju, K.G. Abhilash, R.S. Menon, and E. Suresh Org. Lett. 7 2005 2121
47. V. Nair, A.T. Biju, A.U. Vinod, and E. Suresh Org. Lett. 7 2005 5139
48. X. Li, Z. Xi, S. Luo, and J.-P. Cheng Adv. Synth. Catal. 352 2010 1097
49. X. Li, S. Hu, Z. Xi, L. Zhang, S. Luo, and J.-P. Cheng J. Org. Chem. 75 2010 8697
50. C. Liu, B.-X. Tan, J.-L. Jin, Y.-Y. Zhang, N. Dong, X. Li, and J.-P. Cheng J. Org. Chem. 76 2011 5838
51. X. Li, X.-S. Xue, C. Liu, B. Wang, B.-X. Tan, J.-L. Jin, Y.-Y. Zhang, N. Dong, and J.-P. Cheng Org. Biomol. Chem. 10 2012 413
52. X. Li, Y.-Y. Zhang, X.-S. Xue, J.-L. Jin, B.-X. Tan, C. Liu, N. Dong, and J.-P. Cheng Eur. J. Org. Chem. 2012 1774
53. X. Li, C. Yang, J.-L. Jin, X.-S. Xue, and J.-P. Cheng Chem. Asian J. 8 2013 997
54. CCDC 932053 contains the supplementary crystallographic data for compound 5a. This data can be obtained free of charge from the Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data-request/cif.