Synthesis of cyclopentadiene-fused chromanones via one-pot multicomponent reactions

Journal of Organic Chemistry

Volumn 78, Issue 6, 2013, Pages 2611-2616

  Ghandi, Mehdi ^a   Ghomi, Ali Tabatabaei ^a   Kubicki, MacIej ^b  

^a UNIVERSITY OF TEHRAN   (Iran)

^b ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

2-HYDROXYBENZALDEHYDES; ETHYLACETOACETATE; FUNCTIONALIZED; MICHAEL ADDITIONS; MULTI-COMPONENT REACTIONS; ONE POT; ONE-POT METHOD; ZWITTERIONIC INTERMEDIATE;

ADDITION REACTIONS; CARBOXYLATION; CYANIDES; CYCLIZATION; OLEFINS; SCAFFOLDS;

REACTION INTERMEDIATES;

CHROMAN DERIVATIVE; CYCLOPENTADIENE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CROSS LINKING; MICHAEL ADDITION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84875147954     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302790y     Document Type: Article

References (50)

1. Zhu, J. and Bienamye, H. Multicomponent Reactions; VCH: Weinheim, 2005.
2. Simon, C.; Constantieux, T.; Rodriguez, J. Eur. J. Org. Chem. 2004, 4957-4980
3. Murakami, M. Angew. Chem., Int. Ed. 2003, 42, 718-720
4. Jacobi Von Vangelin, A.; Neumann, H.; Grdes, D.; Klaus, S.; Strübing, D.; Beller, M. Chem.-Eur. J. 2003, 9, 4286-4294
5. Balme, G.; Bossharth, E.; Monterio, N. Eur. J. Org. Chem. 2003, 4101-4111
6. Dömling, A. Chem. Rev. 2006, 106, 17-89
7. Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51-80
8. Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathen, J. S.; Balagopal, L. Acc. Chem. Res. 2003, 36, 899-907
9. Ugi, I.; Verner, B.; Dmling, A. Molecules 2003, 8, 53-66
10. Zhu, J. Eur. J. Org. Chem. 2003, 1133-1144
11. Zhou, L. H.; Su, G.; Zhang, W.; Yan, B. J. Comb. Chem. 2009, 11, 1083-1093
12. Lu, K.; Luo, T.; Xiang, Z.; You, Z.; Fathi, R.; Chen, J.; Yang, Z. J. Comb. Chem. 2005, 7, 958-967
13. Zhu, J. Eur. J. Org. Chem. 2003, 1133-1144
14. Weber, L. Curr. Med. Chem. 2002, 9, 1241-1253
15. Bienayme, H.; Hulme, C.; Oddon, G.; Schmidt, P. Chem.-Eur. J. 2000, 6, 3321-3329
16. R. Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471-1499
17. Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210
18. Lee, D.; Sello, J. K.; Schreiber, S. L. Org. Lett. 2000, 2, 709-712
19. Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, A. D.; Thomas, A. K. Acc. Chem. Res. 1996, 29, 123-131
20. Hall, D. G.; Manku, S.; Wang, F. J. Comb. Chem. 2001, 3, 125-150
21. Nicolaou, K. C.; Pfefferkorn, J. A.; Barluenga, S.; Mitchell, H. J.; Roecker, A. J.; Cao, G.-Q. J. Am. Chem. Soc. 2000, 122, 9968-9976
22. Wipf, P.; Reeves, J. T.; Balachandran, R.; Giuliano, K. A.; Hamel, E.; Day, B. W. J. Am. Chem. Soc. 2000, 122, 9391-9395
23. Boger, D. L.; Fink, B. E.; Hedrick, M. P. J. Am. Chem. Soc. 2000, 122, 6382-6394
24. Lee, K. J.; Angulo, A.; Ghazal, P.; Janda, K. D. Org. Lett. 1999, 1, 1859-1862
25. Xu, R.; Greiveldinger, G.; Marenus, L. E.; Cooper, A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 4898-4899
26. Nicolaou, K. C.; Winssinger; Vourloumis, D. T. J. Am. Chem. Soc. 1998, 120, 10814-10826
27. Ugi, I. Angew. Chem., Int. Ed. 1962, 1, 8-20
28. Winterfeldt, E.; Schumann; Dillinger, H. J. Chem. Ber. 1969, 102, 1656-1664
29. Stachulski, A. V.; Berry, N. G.; Low, A. C. L.; Moores, S. L.; Row, E.; Warhurst, D. C.; Adagu, I. S.; Rossignol, J.-F. J. Med. Chem. 2006, 49, 1450-1454
30. Nawrot-Modranka, J.; Nawrot, E.; Graczyk, J. Eur. J. Med. Chem. 2006, 41, 1301-1309
31. Zarganes-Tzitzikas, T.; Terzidis, M. A.; Stephanidou-Stephanatou, J.; Tsoleridis, C. A.; Kostakis, J. E. J. Org. Chem. 2011, 76, 9008-9014
32. Terzidis, M. A.; Stephanidou-Stephanatou, J.; Tsoleridis, C. A. J. Org. Chem. 2010, 75, 1948-1955
33. Nawrot-Modranka, J.; Nawrot, E.; Graczyk, J. Eur. J. Med. Chem. 2006, 41, 1301-1309
34. Kirkiacharian, S.; Thuy, D. T.; Sicsic, S.; Bakhchinian, R.; Kurkjian, R.; Tonnaire, T. Farmaco 2002, 57, 703-708
35. Mao, P.C.-M.; Mouscadet, J. F.; Leh, H.; Auclair, C.; Hsu, L. Y. Chem. Pharm. Bull. (Tokyo) 2002, 50, 1634-1637 (c)
36. Kawase, M.; Varu, B.; Shah, A.; Motohashi, N.; Tani, S.; Saito, S.; Debnath, S.; Mahapatra, S.; Dastidar, S. G.; Chakrabarty, A. N. Arzneim.-Forsch./Drug Res. 2001, 51, 67-71
37. Kayser, O.; Kolodziej, H. Z. Naturforsch. 1999, 54, 169-174
38. Jimenez-Orozco, F. A.; Lopez-Gonzalez, J. S.; Nieto-Rodriquez, A.; Velasco-Velazquez, M. A.; Molina-Guarneros, J. A.; Mendoza-Patino, N.; Garcia-Mondragon, M. J.; Elizalde-Galvan, P.; Leon-Cedeno, F.; Mandoki, J. J. Lung Cancer 2001, 34, 185-194
39. Valenti, P.; Fabbri, G.; Rampa, A.; Bisi, A.; Gobbi, S.; Da Re, P.; Carrara, M.; Sgevano, A.; Cima, L. Anti-Cancer Drug Des. 1996, 11, 243-252
40. Kamat, D. P.; Tilve, S. G.; Kamat, V. P. Tetrahedron Lett. 2012, 53, 4469-4472
41. Neel, M.; Gouin, J.; Voituriez, A.; Marinett, A. Synthesis 2011, 2003-2009
42. Ghandi, M.; Zarezadeh, N.; Taheri, A. Tetrahedron Lett. 2012, 53, 3353-3356
43. Ghandi, M.; Zarezadeh, N.; Taheri, A. Tetrahedron Lett. 2011, 52, 1228-1232
44. Ghandi, M.; Zarezadeh, N.; Taheri, A. Tetrahedron 2010, 66, 8231-8237
45. Nair, V.; Vinod, A. U.; Abhilash, N.; Menon, R. S.; Santhi, V.; Varma, R. L.; Viji, S.; Mathew, S.; Srinivas, R. Tetrahedron 2003, 59, 10279-10286
46. Junjappa, H.; Saxena, M. K.; Ramaiah, D.; Loharay, B. B.; Rath, N. P.; George, M. V. J. Org. Chem. 1998, 63, 9801-9805
47. Dillinger, H. J.; Fengler, G.; Schumann, D.; Winterfeldt, E. Tetrahedron 1974, 30, 2553-2559
48. Oakes, T. R.; David, H. G.; Nagel, F. J. J. Am. Chem. Soc. 1969, 91, 4761-4765
49. Winterfeldt, E.; Giesler, G. Chem. Ber. 1968, 101, 4022-4031
50. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, Part A: Structure and Mechanisms, 5 th ed.; Springer: New York, 2007; 344.