Investigation towards an efficient synthesis of benzo[g]isoquinoline-1,5, 10(2H)-triones

Tetrahedron

Volumn 67, Issue 45, 2011, Pages 8747-8756

  Mbala, Blaise Mavinga ^a   Jacobs, Jan ^a   Claes, Pieter ^a   Mudogo, Virima ^b   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

^b UNIVERSITY OF KINSHASA   (Congo)

Author keywords

Benzo g furo 4,3,2 de isoquinoline 2,5(4H) diones; Benzo g isoquinoline 1,5, 10(2H) triones; Nenitzescu reaction; Pentalongin

Indexed keywords

1,4 DIHYDROXY 2 NAPHTHOIC ACID; 1,4 DIHYDROXYNAPHTHALENE 2 CARBOXYLATE; 2 ETHYL 3 METHYL 1,2,5,10 TETRAHYDRO 1,5,10 TRIOXOBENZO[G]ISOQUINOLINE 4 CARBOXYLIC ACID; 2 METHOXYCARBONYL 1,4 NAPHTHOQUINONE; 2,3 DIETHYL 1,2,5,10 TETRAHYDRO 1,5,10 TRIOXOBENZO[G]ISOQUINOLINE 4 CARBOXYLIC ACID; 2,3 DISUBSTITUTED BENZO[G]ISOQUINOLINE 1,5,10 (2H)TRIONE DERIVATIVE; 3,4 DIETHYL 6 HYDROXYBENZO[G]FURO [4,3,2 DE]ISOQUINOLINE 2,5 (4H)DIONE; 3,4 DISUBSTITUTED 6 HYDROXYBENZO[G]FURO [4,3,2 DE]ISOQUINOLINE 2,5 (4H)DIONE DERIVATIVE; 4 ETHYL 6 HYDROXY 3 METHYLBENZO[G]FURO [4,3,2 DE]ISOQUINOLINE 2,5 (4H)DIONE; 6 HYDROXY 3 METHYL 4 PROPYLBENZO[G]FURO [4,3,2 DE]ISOQUINOLINE 2,5 (4H)DIONE; AMINE; BETA OXOCARBOXYLIC ACID ESTER; ESTER DERIVATIVE; ETHYL 2 ETHYL 3 PHENYL 1,2,5,10 TETRAHYDRO 1,5,10 TRIOXOBENZO[G]ISOQUINOLINE 4 CARBOXYLATE; ETHYL 3 METHYL 2 PROPYL 1,2,5,10 TETRAHYDRO 1,5,10 TRIOXOBENZO[G]ISOQUINOLINE 4 CARBOXYLATE; ETHYL 3 PHENYL 2 PROPYL 1,2,5,10 TETRAHYDRO 1,5,10 TRIOXOBENZO[G]ISOQUINOLINE 4 CARBOXYLATE; ISOQUINOLINE DERIVATIVE; METHYL 1,2 DIHYDRO 5,10 DIHYDROXY 2 ETHYL 3 METHYL 1 OXOBENZO[G]ISOQUINOLINE 4 CARBOXYLATE; METHYL 2 3 DIETHYL 1,2,5,10 TETRAHYDRO 1,5,10 TRIOXOBENZO[G]ISOQUINOLINE 4 CARBOXYLATE; METHYL 2 ETHYL 3 METHYL 1,2,5,10 TETRAHYDRO 1,5,10 TRIOXOBENZO[G]ISOQUINOLINE 4 CARBOXYLATE; METHYL 2 PROPYL 3 METHYL 1,2,5,10 TETRAHYDRO 1,5,10 TRIOXOBENZO[G]ISOQUINOLINE 4 CARBOXYLATE; METHYL 2,3 DIHYDRO 5 HYDROXY 2 OXONAPHTHO [1,2 BETA]FURAN 4 CARBOXYLATE; METHYL 2,3 DIHYDRO 5 HYDROXY 3 (1 OXO PROPYL)NAPHTHO [1,2-BETA]FURAN 4 CARBOXYLATE; METHYL 2,3 DIHYDRO 5 HYDROXY 3 (1 OXOISOBUTYRYL)NAPHTHO [1,2 BETA]FURAN 4 CARBOXYLATE; METHYL 3 ACETYL 2,3 DIHYDRO 5 HYDROXY 2 OXONAPHTHO[1,2 BETA]FURAN 4 CARBOXYLATE; METHYL 3 BENZOYL 2,3 DIHYDRO 5 HYDROXY 2 OXO NAPHTHO [1,2 BETA]FURAN 4 CARBOXYLATE; METHYL 3 ETHYL 2 PROPYL 1,2,5,10 TETRAHYDRO 1,5,10 TRIOXOBENZO[G]ISOQUINOLINE 4 CARBOXYLATE; METHYL 5 HYDROXY 2 METHYLNAPHTHO [1,2 BETA]FURAN 4 CARBOXYLATE; NAPHTHOQUINONE; SUBSTITUTED BENZO[G]ISOQUINOLINE 1,5,10 (2H)TRIONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; OXIDATION; PRIORITY JOURNAL; SYNTHESIS;

PENTAS LONGIFLORA;

EID: 80053581282     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.09.021     Document Type: Article

References (54)

1. J. Sperry, I. Lorenzo-Castrillejo, M.A. Brimble, and F. Machín Bioorg. Med. Chem. 17 2009 7131 7137
2. M.A. Brimble, L.J. Duncalf, and M.R. Nairn Nat. Prod. Rep. 16 1999 267 281
3. J. Sperry, P. Bachu, and M.A. Brimble Nat. Prod. Rep. 25 2008 376 400
4. S.R. Jammula, S.B. Pepalla, H. Telikepalli, K.V.J. Rao, and R.H. Thomson Phytochemistry 30 1991 3741 3744
5. S. Claessens, G. Verniest, J. Jacobs, E. Van Hende, P. Habonimana, T. Nguyen Van, L. Van Puyvelde, and N. De Kimpe Synlett 2007 829 850
6. B. Kesteleyn, and N. De Kimpe J. Org. Chem. 64 1999 1173 1179
7. B. Kesteley, N. De Kimpe, and L. Van Puyvelde Syntheis 1999 1881 1883
8. A. Plubrukarn, S. Yuenyongsawad, T. Thammasaroj, and A. Jitsue Pharm. Biol. 41 2003 439 442
9. G.P. Arsenault Tetrahedron Lett. 45 1965 4033 4037
10. P.S. Steyn, P.L. Wessels, and W.F.O. Marasas Tetrahedron 35 1979 1551 1555
11. P.N. Solis, C. Langat, M.P. Gupta, G.C. Kirby, D.S. Warhurst, and J.D. Phillipson Planta Med. 61 1995 62 65
12. J.D. Phillipson Phytochemistry 38 1995 1319 1343
13. B. Kesteleyn, and N. De Kimpe J. Org. Chem. 65 2000 640 644
14. Y. Moriyasu, H. Miyagawa, N. Hamada, H. Miyakawi, and T. Ueno Phytochemistry 58 2001 239 241
15. A. Miljkovic, P.G. Mantle, D.J. Williams, and B. Rassing J. Nat. Prod. 64 2001 1251 1253
16. D. Parisot, M. Devys, M.Z. Barbier, and B. Naturforsch Tetrahedron 44 1989 1473 1474
17. T. Nguyen Van, G. Verniest, S. Claessens, and N. De Kimpe Tetrahedron 61 2005 2295 2300
18. J.A. Valderrama, M.F. Gonzalez, D. Pessoa-Mahana, R.A. Tapia, H. Fillion, F. Pautet, J.A. Rodriguez, C. Theoduloz, and G. Schmeda-Hirschmann Bioorg. Med. Chem. 14 2006 5003 5011
19. T. Choshi, T. Kumermura, J. Nobuhiro, and S. Hibino Tetrahedron Lett. 49 2008 3727 3728
20. M. Croisy-Delcey, and L. Bisagni J. Chem. Soc., Chem. Commun. 1984 897 898
21. A.A. Armamonov, T. Shneider, and N.V. Baranova Chem. Heterocycl. Compd. 16 1980 397 401
22. D.W. Cameron, K.R. Deutscher, G.I. Feutrill, and D.E. Hunt Aust. J. Chem. 35 1982 1451 1468
23. T. Welzel, D. Weib, R. Beckert, and H. Gorls Z. Naturforsh. 65b 2010 833 842
24. A.S. Rebstock, F. Mongin, F. Trecourt, and G. Quéguiner Org. Biomol. Chem. 2 2004 291 295
25. J. Jacobs, S. Claessens, B.M. Mbala, K. Huygen, and N. De Kimpe Tetrahedron 65 2009 1193 1199
26. J. Jacobs, B.M. Mbala, B. Kesteleyn, G. Diels, and N. De Kimpe Tetrahedron 64 2008 6364 6371
27. J. Jacobs, B. Kesteleyn, and N. De Kimpe Tetrahedron 64 2008 4985 4992
28. J. Jacobs, J. Deblander, B. Kesteleyn, K. Abbaspour Tehrani, and N. De Kimpe Tetrahedron 64 2008 5345 5353
29. S. Claessens, J. Jacobs, and N. De Kimpe Synlett 2007 741 744
30. J. Jacobs, S. Claessens, B. Kesteleyn, K. Huygen, and N. De Kimpe Tetrahedron 63 2007 2505 2510
31. J. Jacobs, B. Kesteleyn, and N. De Kimpe Tetrahedron 64 2008 7545 7554
32. D.L. Sloman, B. Mitasev, S.S. Scully, J.A. Beutler, and J.A. Porco Jr. Angew. Chem., Int. Ed. 50 2011 2511 2515
33. R. Ratnayake, E. Lacey, S. Tennant, J.H. Gill, and R.J. Capon Chem. - Eur. J. 13 2007 1610 1619
34. H.J. Lee, S.Y. Park, J.S. Kim, H.M. Song, M.E. Suh, and C.O. Lee Bioorg. Med. Chem. 11 2003 4791 4796
35. M. Makosza, and S. Nizamov Tetrahedron 57 2001 9615 9621
36. J. Aleman, B. Richter, and J.A. Jorgensen Angew. Chem. 46 2007 5515 5518
37. G.A. Reynolds, J.A. Van Allan, and R.E. Adel J. Org. Chem. 30 1965 3819 3824
38. E. Widmer, J.W. Meyer, A. Walser, and E. Hardegger Helv. Chim. Acta 48 1965 538 555
39. C.M. Tseng, Y.L. Wu, and C.P. Chuang Tetrahedron 60 2004 12249 12260
40. C.M. Tseng, Y.L. Wu, and C.P. Chuang Tetrahedron 58 2002 7625 7633
41. A.I. Tsai, Y.L. Wu, and C.P. Chuang Tetrahedron 57 2001 7829 7837
42. S.F. Wang, C.P. Chuang, and J.H. Lee Heterocycles 50 1999 489 497
43. C.P. Chuang, and S.F. Wang Tetrahedron 54 1998 10043 10052
44. W.S. Murphy, D. Neville, and G. Ferguson Tetrahedron Lett. 37 1996 7615 7618
45. N.V.S. Mudiganti, S. Claessens, and N. De Kimpe Tetrahedron 65 2009 1716 1723
46. K.K. Irikura, M. Meot-Ner, and L.W. Sieck J. Org. Chem. 61 1996 3167 3171
47. C.D. Nenitzescu Bull. Soc. Chim. Romania 11 1929 37 43
48. G.R. Allen, and M.J. Weiss J. Org. Chem. 33 1968 198 200
49. L.W. Schenck, A. Sippel, K. Kuna, W. Frank, A. Albert, and U. Kucklaender Tetrahedron 61 2005 9129 9139
50. U. Kucklander, H. Pitzler, and K. Kuna Arch. Pharmacol. 327 1994 137 142
51. V.M. Lyubchanskaya, L.M. Alekseeva, S.A. Savina, A.S. Shashkov, and V.G. Granik Russ. Chem. Bull. 51 2002 1886 1893
52. S.A. Patil, R. Patil, and D. Miller Curr. Org. Chem. 12 2008 691 717
53. J.A. Valderrama, J.A. Ibacache, V. Arancibia, J. Rodriguez, and C. Theoduloz Bioorg. Med. Chem. 17 2009 2894 2901
54. P.G. Baraldi, D. Simoni, and S. Manfredini Synthesis 1983 902 903