A copper(II) perchlorate-promoted tandem reaction of internal alkynol and salicyl N-tosylhydrazone: Direct access to isochromeno[3,4-b]chromene

Chemical Communications

Volumn 50, Issue 62, 2014, Pages 8514-8517

  Siyang, Hai Xiao ^a   Wu, Xu Rui ^a   Ji, Xiao Yue ^a   Wu, Xin Yan ^a   Liu, Pei Nian ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; CHROMENE DERIVATIVE; CUPRIC ION; DIOXANE; HYDRAZONE DERIVATIVE; ISOCHROMENO[3,4 B]CHROMENE; NATURAL PRODUCT; PERCHLORATE; SALICYLIC ACID; TOLUENE; UNCLASSIFIED DRUG; ALKYNE; BENZOPYRAN DERIVATIVE; COPPER; COPPER(II) PERCHLORATE;

ACETALIZATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; CYCLOISOMERIZATION; ELECTROPHILICITY; ELIMINATION REACTION; STEREOSPECIFICITY; CHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

ALKYNES; BENZOPYRANS; CATALYSIS; COPPER; CYCLOADDITION REACTION; HYDRAZONES; MOLECULAR STRUCTURE; PERCHLORATES; X-RAY DIFFRACTION;

EID: 84904088227     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc02862g     Document Type: Article

References (49)

1. F. Perron, K. F. Albizati, Chem. Rev. 1989, 89, 1617.
2. D. O'Hagan, Nat. Prod. Rep. 1995, 12, 1.
3. R. D. Norcross, I. Paterson, Chem. Rev. 1995, 95, 2041.
4. J. E. Aho, P. M. Pihko, T. K. Rissa, Chem. Rev. 2005, 105, 4406.
5. B. R. Raju, A. K. Saikia, Molecules, 2008, 13, 1942.
6. S. Favre, P. Vogel, S. Gerber-Lemaire, Molecules, 2008, 13, 2570.
7. J. Sperry, Z. E. Wilson, D. C. K. Rathwell, M. A. Brimble, Nat. Prod. Rep. 2010, 27, 1117.
8. B. Fraser-Reid, L. Magdzinski, B. F. Molino, D. R. Mootoo, J. Org. Chem. 1987, 52, 4495.
9. D. R. Mootoo, B. Fraser-Reid, J. Org. Chem. 1989, 54, 5548.
10. G. V. Baddeley, J. J. H. Simes, T.-H. Ai, Aust. J. Chem. 1980, 33, 2071.
11. E. E. Waldner, M. Hesse, W. I. Taylor, H. Schmid, Helv. Chim. Acta, 1967, 50, 1926.
12. C. Audin, J.-M. Lancelin, J.-M. Beau, Tetrahedron Lett. 1988, 29, 3691.
13. N. Moufid, Y. Chapleur, P. Mayon, J. Chem. Soc. Perkin Trans. 1, 1992, 999.
14. O. Rhode, H. M. R. Hoffmann, Tetrahedron, 2000, 56, 6479.
15. T. Mikami, A. Katoh, O. Mitsunobu, Tetrahedron Lett. 1990, 31, 539.
16. N. Beaulieu, R. A. Dickinson, P. Deslongchamps, Can. J. Chem. 1980, 58, 2531.
17. P. Duhamel, A. Deyine, G. Dujardin, G. Plé, J.-M. Poirier, J. Chem. Soc. Perkin Trans. 1, 1995, 2103.
18. F. Wang, M. Qu, X. Lu, F. Chen, M. Shi, Chem. Commun. 2012, 48, 6259.
19. C. Taillefumier, Y. Chapleur, D. Bayeul, A. Aubry, J. Chem. Soc. Chem. Commun. 1995, 937.
20. C. Taillefumier, Y. Chapleur, Can. J. Chem. 2000, 78, 708.
21. R. S. Kumar, R. Nagarajan, P. T. Perumal, Synthesis, 2004, 949.
22. J. Wang, F.-X. Xu, X.-F. Lin, Y.-G. Wang, Tetrahedron Lett. 2008, 49, 5208.
23. L. Diao, C. Yang, P. Wan, J. Am. Chem. Soc. 1995, 117, 5369.
24. R. M. Jones, C. Selenski, T. R. R. Pettus, J. Org. Chem. 2002, 67, 6911.
25. A. Tenaglia, F. Karl, Synlett, 1996, 327.
26. J. S. Yadav, B. V. S. Reddy, L. Chandraiah, B. Jagannadh, S. K. Kumar, A. C. Kunwar, Tetrahedron Lett. 2002, 43, 4527.
27. J. S. Yadav, B. V. S. Reddy, M. Aruna, C. Venugopal, T. Ramalingam, S. K. Kumar, A. C. Kunwar, J. Chem. Soc. Perkin Trans. 1, 2002, 165.
28. M. Anniyappan, D. Muralidharan, P. T. Perumal, Tetrahedron, 2002, 58, 10301.
29. J. S. Yadav, B. V. S. Reddy, C. Madhuri, G. Sabitha, B. Jagannadh, S. K. Kumar, A. C. Kunwar, Tetrahedron Lett. 2001, 42, 6381.
30. J.-i. Matsuo, S. Sasaki, H. Tanaka, H. Ishibashi, J. Am. Chem. Soc. 2008, 130, 11600.
31. M. M. A. R. Moustafa, A. C. Stevens, B. P. Machin, B. L. Pagenkopf, Org. Lett. 2010, 12, 4736.
32. B. Alcaide, P. Almendros, J. M. Alonso, Org. Biomol. Chem. 2011, 9, 4405.
33. A. Corma, A. Leyva-Pérez, M. J. Sabater, Chem. Rev. 2011, 111, 1657.
34. B. Alcaide, P. Almendros, J. M. Alonso, Molecules, 2011, 16, 7815.
35. S. F. Tlais, G. B. Dudley, Beilstein J. Org. Chem. 2011, 7, 570.
36. X. Zeng, Chem. Rev. 2013, 113, 6864.
37. L. Zhou, Y. Shi, Q. Xiao, Y. Liu, F. Ye, Y. Zhang, J. Wang, Org. Lett. 2011, 13, 968.
38. N. D. Paul, S. Mandal, M. Otte, X. Cui, X. P. Zhang, B. D. Bruin, J. Am. Chem. Soc. 2014, 136, 1090.
39. P. N. Liu, F. H. Su, T. B. Wen, H. H.-Y. Sung, I. D. Williams, G. Jia, Chem. - Eur. J. 2010, 16, 7889.
40. D. Y. Li, X. S. Shang, G. R. Chen, P. N. Liu, Org. Lett. 2013, 15, 3848.
41. H. X. Siyang, X. R. Wu, H. L. Liu, X. Y. Wu, P. N. Liu, J. Org. Chem. 2014, 79, 1505.
42. D. Végh, P. Zalupsky, J. Kováč, Synth. Commun. 1990, 20, 1113.
43. B. Gabriele, G. Salerno, E. Lauria, J. Org. Chem. 1999, 64, 7687.
44. Y. Liu, F. Song, Z. Song, M. Liu, B. Yan, Org. Lett. 2005, 7, 5409.
45. J. Barluenga, A. Diéguez, A. Fernández, F. Rodríguez, F. J. Fañanás, Angew. Chem. Int. Ed. 2006, 45, 2091.
46. M. Rueping, M.-Y. Lin, Chem. - Eur. J. 2010, 16, 4169.
47. H. Wu, Y.-P. He, L.-Z. Gong, Org. Lett. 2013, 15, 460.
48. T. Sordo, P. Campomanes, A. Diéguez, F. Rodríguez, F. J. Fañanás, J. Am. Chem. Soc. 2005, 127, 944.
49. J. Barluenga, A. Diéguez, F. Rodríguez, F. J. Fañanás, T. Sordo, P. Campomanes, Chem. - Eur. J. 2005, 11, 5735.