Pyrrolidine and iodine catalyzed domino aldol-Michael-dehydrogenative synthesis of flavones

Tetrahedron Letters

Volumn 55, Issue 22, 2014, Pages 3340-3343

  Naik, Mayuri M ^a   Tilve, Santosh G ^a   Kamat, Vijayendra P ^a  

^a GOA UNIVERSITY   (India)

Author keywords

Aldol; Domino; Flavones; Iodine; Pyrrolidine

Indexed keywords

2' HYDROXYACETOPHENONE DERIVATIVE; ACETOPHENONE DERIVATIVE; ALDEHYDE; DIMETHYL SULFOXIDE; FLAVONE DERIVATIVE; IODINE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG STRUCTURE; ONE POT SYNTHESIS; OXIDATION;

EID: 84901201838     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.04.051     Document Type: Article

References (72)

1. E. Middleton Jr. Adv. Exp. Med. Biol. 439 1998 175 182
2. S.A. Aherne, and N.M. O'Brien Nutrition 18 2002 75 81
3. The Flavonoids, advances in research since 1986 J.B. Harborne 1986 Chapman and Hall London 1993
4. J.A. Seijas, M.P. Vázquez-Tato, and R. Carballido-Reboredo J. Org. Chem. 70 2005 2855 2858 and references cited therein
5. A.K. Verma, and R. Pratap Tetrahedron 68 2012 8523 8538 and references cited therein
6. F. Orallo Curr. Med. Chem. 15 2008 1887 1898
7. X.H. Han, S.S. Hong, J.S. Hwang, M.K. Lee, B.Y. Hwang, and J.S. Ro Arch. Pharm. Res. 30 2007 13 17
8. S. Öksüz, H. Ayyildiz, and C. Johansson J. Nat. Prod. 47 1984 902 903
9. Y. Lin, R. Shi, X. Wang, and H.M. Shen Curr. Cancer Drug Targets 8 2008 634 646
10. S. Martens, and A. Mithöfer Phytochemistry 66 2005 2399 2407
11. J. Gabrielska, M. Soczyńska-Kordala, and S. Przestalski J. Agric. Food Chem. 53 2005 76 83
12. W. Baker J. Chem. Soc. 1933 1381 1389
13. H.S. Mahal, and K. Venkataraman J. Chem. Soc. 1934 1767 1769
14. H.S. Mahal, and K. Venkataraman Curr. Sci. 4 1933 214 216
15. T.S. Wheeler Org. Synth. 32 1952 72
16. T.S. Wheeler Org. Synth. 4 1963 478 For recent examples of the Baker-Venkataraman rearrangement, see
17. C. Riva, C. De Toma, L. Donadd, C. Boi, R. Pennini, G. Motta, and A. Leonardi Synthesis 1997 195 201
18. F. Bois, C. Beney, A.M. Mariotte, and A. Boumendjel Synlett 1999 1480 1482
19. A.K. Ganguly, S. Kaur, P.K. Mahata, D. Biswas, B.N. Pramanik, and T.M. Chan Tetrahedron Lett. 46 2005 4119 4121
20. A.K. Ganguly, P.K. Mahata, and D. Biswas Tetrahedron Lett. 47 2006 1347 1349
21. C.F. Chee, M.J.C. Buckle, and N.A. Rahman Tetrahedron Lett. 52 2011 3120 3123
22. J. Allan, and R. Robinson J. Chem. Soc. 125 1924 2192 2195
23. K.V. Auwers, and T. Markovists Ber. Dtsch. Chem. Ges. 41 1908 2332 2340
24. K.V. Auwers, and P. Pohl Ber. Dtsch. Chem. Ges. 48 1915 85 90
25. K.V. Auwers Ber. Dtsch. Chem. Ges. 49 1916 809 819
26. K.V. Auwers, and P. Pohl Liebigs Ann. Chem. 405 1914 243 294
27. K.V. Sashidhara, M. Kumar, and A. Kumar Tetrahedron Lett. 53 2012 2355 2359
28. P. Venkatesan, and T. Maruthavanan Bull. Chem. Soc. Ethiop. 25 2011 419 425
29. D.N. Theja, T.P. Choudary, M.I. Reddy, G. Avsss, and K.U. Reddy Int. J. Pharm. Pharm. Sci. 3 2011 51 54
30. K.R. Babu, K.V. Kumar, M. Vijaya, and V. Madhavarao Int. J. Pharm. Technol. 4 2012 3943 3950
31. S.R. Sarda, W.N. Jadhav, and R.P. Pawar Int. J. ChemTech. Res. 1 2009 539 543
32. P.S. Kulkarni, D.D. Kondhare, R. Varala, and P.K. Zubaidha J. Serb. Chem. Soc. 77 2012 1 12
33. N. Ahmed, H. Ali, and J.E. Van Lier Tetrahedron Lett. 46 2005 253 256
34. M.J. Menezes, S. Manjrekar, V. Pai, R.E. Patre, and S.G. Tilve Indian J. Chem. 48B 2009 1311 1314
35. S.L. Borse, M.R. Patel, and L.B. Borse Int. J. Pharm. Res. Dev. 3 2011 147 152
36. J.A. Seijas, M.P. Vázquez-Tato, and R. Carballido-Reboredo J. Org. Chem. 70 2005 2855 2858
37. G.W. Kabalka, and A.R. Mereddy Tetrahedron Lett. 46 2005 6315 6317
38. M. Muthukrishnan, P.S. Patil, S.V. More, and R.A. Joshi Mendeleev Commun. 15 2005 100 101 and references cited therein
39. O.V. Singh, M. Muthukrishnan, and G. Raj Synth. Commun. 35 2005 2723 2728 and references cited therein
40. P. Bovicelli, V. D'Angelo, D. Collalto, A. Verzina, N. D'Antona, and D. Lambusta J. Pharm. Pharmacol. 59 2007 1697 1701
41. Z. Zhou, P. Zhao, W. Huang, and G. Yang Adv. Synth. Catal. 348 2006 63 67
42. M. Lamba, and J.K. Makrandi J. Chem. Res. 2008 2008 225 226
43. E. Awuah, and A. Capretta Org. Lett. 11 2009 3210 3213
44. M. Lorenz, M.S. Kabir, and J.M. Cook Tetrahedron Lett. 51 2010 1095 1098
45. D. Kim, K. Ham, and S. Hong Org. Biomol. Chem. 10 2012 7305 7312
46. G.A. Kraus, and V. Gupta Org. Lett. 12 2010 5278 5280
47. K.H. Kim, H.S. Lee, S.H. Kim, and J.N. Kim Tetrahedron Lett. 53 2012 2761 2764
48. M. Khoobi, M. Alipour, S. Zarei, F. Jafarpour, and A. Shafiee Chem. Commun. 2012 2985 2987
49. H. Miao, and Z. Yang Org. Lett. 2 2000 1765 1768
50. Q. Yang, and H. Alper J. Org. Chem. 75 2010 948 950
51. X.-F. Wu, H. Neumann, and M. Beller Chem. Eur. J. 18 2012 12595 12598
52. B. Liang, M. Huang, Z. You, Z. Xiong, K. Lu, R. Fathi, J. Chen, and Z. Yang J. Org. Chem. 70 2005 6097 6100
53. S.R. Sarda, M.Y. Pathan, V.V. Paike, P.R. Pachmase, W.N. Jadhav, and R.P. Pawar ARKIVOC xvi 2006 43 48 and references cited therein
54. R.S. Bhosale, S.R. Sarda, R.P. Giram, D.S. Raut, S.P. Parwe, S.S. Ardhapure, and R.P. Pawar J. Iran. Chem. Soc. 6 2009 519 522 and references cited therein
55. Z. Du, H. Ng, K. Zhang, H. Zeng, and J. Wang Org. Biomol. Chem. 9 2011 6930 6933
56. J.I. Lee, H.S. Son, and H. Park Bull. Korean Chem. Soc. 25 2004 1945 1947
57. J.I. Lee, H.S. Son, and M.G. Jung Bull. Korean Chem. Soc. 26 2005 1461 1463
58. D. Nagarathnam, and M. Cushman J. Org. Chem. 56 1991 4884 4887
59. D.O. Bennardi, G.P. Romanelli, J.L. Jios, J.C. Autino, G.T. Baronetti, and H.J. Thomas ARKIVOC xi 2008 123 130
60. M.E. Pérez, D.M. Ruiz, J.C. Autino, M.N. Blanco, L.R. Pizzio, and G.P. Romanelli J. Porous Mater. 20 2013 1433 1440
61. J. Zhao, Y. Zhao, and H. Fu Org. Lett. 14 2012 2710 2713
62. G. Maiti, R. Karmakar, R.N. Bhattacharya, and U. Kayal Tetrahedron Lett. 52 2011 5610 5612
63. M. Yoshida, Y. Fujino, K. Saito, and T. Doi Tetrahedron 67 2011 9993 9997
64. P. Kumar, and M.S. Bodas Org. Lett. 2 2000 3821 3823
65. J. Das, and S. Ghosh Tetrahedron Lett. 52 2011 7189 7194
66. V.I. Yakovenko, É.T. Oganesyan, and G.N. Dorofeenko Chem. Heterocycl. Compd. 17 1981 115 118
67. A.G. Golub, V.G. Bdzhola, O.V. Ostrynska, I.V. Kyshenia, V.M. Sapelkin, A.O. Prykhod'ko, O.P. Kukharenko, and S.M. Yarmoluk Bioorg. Med. Chem. 21 2013 6681 6689
68. V. Kavala, C. Lin, C.-W. Kuo, H. Fang, and C.-F. Yao Tetrahedron 68 2012 1321 1329
69. T. Kálai, G. Kulcsar, E. Osz, J. Jeko, B. Sumegi, and K. Hidega ARKIVOC vii 2004 266 276
70. C. Zhou, A.V. Dubrovsky, and R.C. Larock J. Org. Chem. 71 2006 1626 1632
71. V.P. Khilya, and V.V. Ishchenko Chem. Heterocycl. Compd. 38 2002 883 899
72. P.D. Lokhande, S.S. Sakate, K.N. Taksande, and B. Navghare Tetrahedron Lett. 46 2005 1573 1574