An efficient one-pot, regio- and stereoselective synthesis of novel pentacyclic-fused pyrano[3,2,c]chromenone or quinolinone benzosultone derivatives in water

Tetrahedron

Volumn 69, Issue 24, 2013, Pages 4979-4989

  Ghandi, Mehdi ^a   Taghi Nazeri, Mohammad ^a   Kubicki, Maciej ^b  

^a UNIVERSITY OF TEHRAN   (Iran)

^b ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

Benzosultones; Fused pyranochromenone; Knoevenagel hetero Diels Alder

Indexed keywords

2 FORMYLPHENYL (E) 2 PHENYLETHENESULFONATE DERIVATIVE; 2 HYDROXYBENZALDEHYDE DERIVATIVE; 2 PHENYLETHENESULFONYL; 4 HYDROXYCOUMARIN DERIVATIVE; 4 HYDROXYQUINOLINONE; BENZALDEHYDE DERIVATIVE; CHROMENE DERIVATIVE; PYRANO [3,2,C] CHROMENONE; PYRANOQUINOLINONE BENZOSULTONE DERIVATIVE; QUINOLINE DERIVATIVE; SULFONIC ACID DERIVATIVE; SULTONE; UNCLASSIFIED DRUG; WATER;

ARTICLE; DIELS ALDER REACTION; DRUG STRUCTURE; KNOEVENAGEL CONDENSATION; ONE POT SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY; SULFONATION;

ALNUS;

EID: 84877584250     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.04.018     Document Type: Article

References (74)

1. P. Borah, P.S. Naidu, and P.J. Bhuyan Tetrahedron Lett. 53 2012 5034 5037
2. Z. Zareai, K. Khoobi, A. Ramazani, A. Foroumadi, A. Souldozi, K. Slepokura, T. Lis, and A. Shafiee Tetrahedron 68 2012 6721 6726
3. R. Durga, R.S. Manian, J. Jayashankaran, and R. Raghunathan Tetrahedron Lett. 48 2007 1385 1389
4. K.C. Majumdar, A. Taher, and P. Ponra Tetrahedron Lett. 51 2010 2297 2300
5. A.T. Khan, D.K. Das, K. Islam, and P. Das Tetrahedron Lett. 53 2012 6418 6422
6. J. Jayashankaran, R. Durga, S. Manian, and R. Raghunathan Tetrahedron Lett. 47 2006 2265 2270
7. T.O. Olomola, R. Klein, K.A. Lobb, Y. Sayed, and P.T. Kaye Tetrahedron Lett. 51 2010 6325 6328
8. A.A. Mahmoud, A.A. Ahmed, M. Linuma, and T. Tanaka Phytochemistry 47 1998 543 544
9. D.A. Mulholland, S.E. Lourine, D.A.H. Taylor, and F.M. Dean Phytochemistry 47 1998 1641 1644
10. M. Shanmugasundaram, S. Manikandan, and R. Raghunatan Tetrahedron 55 2002 997 1003
11. R.P. Rastogi, and B.N. Mehrotra R.P. Rastogi, Compendium Of Indian Medicinal Plants Vol. 3 1993 273
12. M.F. Grundon A. Brossi, Quinoline Alkaloids Related to Anthranilic Acid The Alkaloids Vol. 32 1988 Academic London, UK 341
13. A. Ulubelen, A.H. Mericli, F. Mericli, and Kaya Phytochemistry 35 1994 1600 1601
14. S.-J. Wu, and I.-S. Chen Phytochemistry 34 1993 1659 1661
15. W.E. Campbell, B. Davidowitz, and G.E. Jackson Phytochemistry 29 1990 1303 1306
16. S.A. Khalid, and P.G. Waterman Phytochemistry 20 1981 2761 2763
17. M.S. Hifnawy, J. Vaquette, T. Sévenet, J.-L. Pousset, and A. Cavé Phytochemistry 16 1977 1035 1039
18. F.R. Stermitz, and I.A. Sharifi Phytochemistry 16 1977 2003 2006
19. I.-S. Chen, S.-J. Wu, I.J. Tsai, T.-S. Wu, J.M. Pezzuto, M.C. Lu, H. Chai, N. Suh, and C.-M. Teng J. Nat. Prod. 57 1994 1206 1211
20. S. Manikandan, M. Shanmugasundaram, and R. Raghunathan Tetrahedron 58 2002 8957 8962
21. S. Ahmad J. Nat. Prod. 47 1984 391 392
22. S. Mitaku, A.L. Skaltsounis, F. Tillequin, M. Koch, J. Pusset, and G. Chauviere J. Nat. Prod. 48 1985 772 777
23. K.C. Majumdar, S. Mondal, and D. Ghosh Tetrahedron Lett. 50 2009 4781 4874
24. S. Mondal Chem. Rev. 2012 10.1021/cr2003294
25. D.W. Roberts, D.L. Williams, and D. Bethell Chem. Res. Toxicol. 20 2007 61 67
26. E. Meschkat, M.D. Barratt, and J.-P. Lepoittevin Chem. Res. Toxicol. 14 2001 110 117
27. S. Braverman, T. Pechenick-Azizi, D.T. Major, and M. Sprecher J. Org. Chem. 72 2007 6824 6831
28. D.W. Roberts Org. Process Res. Dev. 2 1998 194 202
29. S. Ma, and Z. Shi J. Org. Chem. 63 1998 6387 6389
30. M.J. Pérez-Péreza, J. Balzarinib, M. Hosoyab, E. De Clercq, and M.J. Camarasa Bioorg. Med. Chem. Lett. 2 1992 697 698
31. D.W. Roberts, and D.L. Williams Tetrahedron 43 1987 1027 1062
32. E.T. Kaiser, and K.W. Lo J. Am. Chem. Soc. 91 1969 4912 4918
33. J. Wolinsky, D.R. Dimmel, and T. Gibson J. Am. Chem. Soc. 89 1967 2087 2097
34. A. Mustafa, and M.K. Hilmy J. Chem. Soc. 1952 1339 1342
35. G. Schetty Helv. Chim. Acta 32 1949 24 30
36. G. Schetty Helv. Chim. Acta 30 1947 1650 1660
37. P. Metz, M. Fleischer, and R. Frohlich Tetrahedron 51 1995 711 732
38. P. Metz, and M. Fleischer Synlett 1993 399 400
39. E. Bovenschult, P. Metz, and G. Henkel Angew. Chem., Int. Ed. Engl. 28 1989 202 203
40. S.A. Wolckenhauer, A.S. Devlin, and J. Du Bois Org. Lett. 9 2007 4363 4366
41. A.L. Flohic, C. Meyer, and J. Cossy Tetrahedron 62 2006 9017 9037
42. A.L. Flohic, C. Meyer, and J. Cossy Org. Lett. 7 2005 339 342
43. J. Cossy, J.-R. Desmurs, and J.-C. Galland Synlett 2003 667 670
44. S. Karsch, P. Schwab, and P. Metz Synlett 2002 2015 2022
45. K. Okuma, M. Koda, S. Maekawa, K. Shioji, T. Inoue, T. Kurisaki, H. Wakita, and Y. Yokomorib Org. Biomol. Chem. 4 2006 2745 2752
46. R.K. Boeckman Jr., S.M. Hanson, and J.A. Cody Heterocycles 70 2006 519 530
47. S. Periyaraja, A.B. Mandal, and P. Shanmugam Org. Lett. 13 2011 4980 4983
48. K.M. Maloney, J.T. Kuethe, and K. Linn Org. Lett. 13 2011 102 105
49. L.F. Tietze, and N. Rackelman J. Zhu, H. Bienayme, Multicomponent Reaction 2005 Wiely-VCH Weinheim, Germany 121 167
50. L.F. Tietze, and N. Rackelmann Pure Appl. Chem. 76 2004 1967 1983
51. L.F. Tietze J. Heterocycl. Chem. 27 1990 47 69
52. L.F. Tietze, N. Rackelmann, and I. Müller Chem. - Eur. J. 10 2004 2722 2731
53. L.F. Tietze, and A. Modi Med. Res. Rev. 20 2000 304 322
54. H.O. House, and T.H. Cronin J. Org. Chem. 30 1965 1061 1070
55. W.R. Roush J. Am. Chem. Soc. 100 1978 3599 3601
56. W.R. Roush, and S.M. Psckis J. Am. Chem. Soc. 103 1981 6696 6704
57. K.J. Sha, and J.W. Gilman Tetrahedron Lett. 24 1983 657 660
58. M. Kiamehr, and F.M. Moghaddam Tetrahedron Lett. 50 2009 6723 6727
59. K.C. Nicolaou, J.A. Pfefferkorn, A.J. Roecker, G.-Q. Cao, S. Barluenga, and H.J. Mitchell J. Am. Chem. Soc. 122 2000 9939 9953
60. D.A. Horton, G.T. Bourne, and M.L. Smythe Chem. Rev. 103 2003 893 930
61. K.C. Nicolaou, J.A. Pfefferkorn, H.J. Mitchell, A.J. Roecker, S. Barluenga, G.-Q. Cao, R.L. Affleck, and J.E. Lillig J. Am. Chem. Soc. 122 2000 9954 9967
62. K.C. Nicolaou, J.A. Pfefferkorn, S. Barluenga, H.J. Mitchell, A.J. Roecker, and G.-Q. Cao J. Am. Chem. Soc. 122 2000 9968 9976
63. P.A. Grieco Organic Synthesis in Water 1998 Blacky Academic & Professional London, UK p. 82
64. U.M. Lindstrom Chem. Rev. 102 2002 2751 2772
65. C.-J. Li Chem. Rev. 105 2005 3095 3166
66. C.-J. Li, and T.-H. Chan Comprehensive Organic Reaction in, Aqueous Media 2007 Wiley and Sons New York, NY
67. M. Ghandi, A. Hasani Bozcheloei, S.H. Nazari, and M. Sadeghzadeh J. Org. Chem. 76 2011 9975 9982
68. Crystallographic Data Centre with the deposition number CCDC-919218. Copies of these, data can be obtained free of charge via http://www.ccdc.cam.ac. uk/conts/retrieving.html (or, from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK; fax: +44 1223 336 033; or e-mail: deposit@ccdc.cam.ac.uk).
69. L.F. Tietze Chem. Rev. 96 1996 115 136
70. M. Ghandi, E. Mohammadimehr, M. Sadeghzadeh, and A. Hasani Bozcheloei Tetrahedron 67 2011 8484 8491
71. F.M. Matloubi, M. Kiamehr, M.R. Khodabakhshi, Z. Mirjafary, S. Fathi, and H. Saeidian Tetrahedron 66 2010 8615 8622
72. K.C. Majumdar, A. Taher, and K. Ray Tetrahedron Lett. 50 2009 3889 3891
73. Y.R. Yong Rok Lee, Y.M. Kim, and S.H. Kim Tetrahedron 65 2009 101 108
74. Y.R. Lee, and T.V. Hung Tetrahedron 64 2008 7338 7346