A facile synthesis of 1,2,3-triazolyl indole hybrids via SbCl3-catalysed Michael addition of indoles to 1,2,3-triazolyl chalcones

Journal of Chemical Sciences

Volumn 124, Issue 4, 2012, Pages 941-950

  Shanmugavelan, Poovan ^a   Sathishkumar, Murugan ^a   Nagarajan, Sangaraiah ^a   Ponnuswamy, Alagusundaram ^a  

^a MADURAI KAMARAJ UNIVERSITY   (India)

Author keywords

1,2,3 triazolyl chalcone; 1,2,3 triazolyl indole; Environmentally benign; Michael addition

Indexed keywords

CATALYSIS; POLYCYCLIC AROMATIC HYDROCARBONS;

1,2,3-TRIAZOLYL INDOLE; CHALCONES; ENVIRONMENTALLY BENIGN; ENVIRONMENTALLY BENIGN SYNTHESIS; FACILE SYNTHESIS; MICHAEL ADDITIONS; SHORT REACTION TIME;

ADDITION REACTIONS;

EID: 84867187207     PISSN: 09743626     EISSN: 09737103     Source Type: Journal    
DOI: 10.1007/s12039-012-0281-x     Document Type: Article

References (67)

1. Nowakowska Z 2007 Eur. J. Med. Chem. 42 125
2. Akihisa T, Tokuda H, Hasegawa D, Ukiya M, Kimura Y and Enjo F 2006 J. Nat. Pro. 69 38
3. Modzelewska A, Pettit C, Achanta G, Davidson N E, Huang, P and Khan S R 2006 Bioorg. Med. Chem. 14 3491
4. Dominguez J N, Leon C, Rodrigues J, Gamboa de Dominguez N, Gut J and Rosenthal P J 2005 J. Med. Chem. 48 3654
5. Nielsen S F, Christensen S B, Cruciani G, Kharazmi A and Liljefors T 1998 J. Med. Chem. 41 4819
6. Yang HM, Shin H R, Cho S H, Bang S C, Song G Y and Ju J H 2007 Bioorg. Med. Chem. 15 104
7. Cheenpracha S, Karalai C, Ponglimanont C, Subhadhirasakul S and Tewtrakul S 2006 Bioorg. Med. Chem. 14 1710
8. Svetaz L, Tapia A, Lopez S N, Furlan R L F, Petenatti E and Pioli R 2004 J. Agri. Food Chem. 52 3297
9. Nerya R, Musa S, Khatib S, Tamir and Vaya J 2004 Phytochemistry 65 1389
10. Aufort M, Herscovici J, Bouhours P, Moreau N and Girard C 2008 Bioorg. Med. Chem. Lett. 18 1195;
11. Wang X L, Wan K and Zhou C H 2010 Eur. J. Med. Chem. 45 4631;
12. Odlo K, Hentzen J, Chabert J F D, Ducki S, Gani, O A B S M, Sylte I, Skrede M, Florenes V A and Hansen T V 2008 Bioorg. Med. Chem. 16 4829
13. Li W T, Wu W H, Tang C H, Tai R and Chen S T 2011 Combinatorial. Sci. 13 72
14. Alvarez R, Velazquez S, San-Felix A, Aquaro S, De Clerq E, Perno C F, Karlsson A, Balzarini J and Camarasa M J 1994 J. Med. Chem. 37 4194
15. Wang S, Wang Q, Wang Y, Liu L, Weng X, Zhang G L X and Zhou X 2008 Bioorg. Med. Chem. Lett. 18 6505
16. Aubry C, Patel A, Mahale S, Chaudhuri B, Marechal J D, Sutcliffe M J and Jenkins P R 2005 Tetrahedron. Lett. 46 1423;
17. Marugan J J, Manthey C, Anaclerio B, Lafrance L, Lu T, Markotan T, Leonard K. A, Crysler C, Eisennagel S, Dasgupta M and Tomczuk B 2005 J. Med. Chem. 48 926;
18. Fukuyama, T and Chen X Q 1994 J. Am. Chem. Soc. 116 3125
19. Zhang H C, Ye H, Moretto A F, Brumfield K K and Maryanoff B E 2000 Org. Lett. 2 89;
20. Faul M M, Winneroski L L and Krumrich C A 1998 J. Org. Chem. 63 6053;
21. Tani M, Matsumoto S, Aida Y, Arikawa S, Nakane A, Yokoyama Y and Murakami Y 1994 Chem. Pharm. Bull. 42 443
22. Gribble G W 2000 J. Chem. Soc. Perkin Trans. 1 1045;
23. Moore R E, Cheuk C, Yan X Q, Patterson G M L, Bonjouklian R, Smitka T A, Mynderse J S, Foster, R S, Jones N D, Swartzendruber, J K and Deeter, J B 1987 J. Org. Chem. 52 1036;
24. Moore R E, Cheuk C, Patterson G M L 1984 J. Am. Chem. Soc. 106 6456
25. Kamalraj V R, Senthil S and Kannan P 2008 J. Mol. Struct. 892 210
26. Iranpoor N, Kazemi F, Iranpoor N and Kazemi E 1998 Tetrahedron. 54 9475;
27. Narender T and Reddy K P 2007 Tetrahedron. Lett. 48 3177
28. Szell T and Sohar I 1969 Can. J. Chem. 47 1254
29. Drexler M T and Amiridis J 2003 J. Catal. 214 136;
30. Choudary B M, Ranganath K V, Yadav, J and Kantam M L 2005 Tetrahedron Lett. 46 1369;
31. Saravanamurugan S, Palanichamy M, Arabindoo B and Murugesan V 2004 J. Mol. Catal. A: Chem. 218 101
32. Daskiewicz J B, Comte G, Barron D, Pietro A D and Thomasson F 1999 Tetrahedron Lett. 40 7095;
33. Sebti S, Solhy A, Smahi A, Kossir A and Oumimoun H 2002 Catal. Commun. 3 335;
34. Wang X and Cheng S 2006 Catal. Commun. 7 689
35. Yang S D, Wu L Y, Yan ZY, Pan Z L and Liang Y M 2007 J. Mol. Catal. A: Chem. 268 107;
36. Dong F, Jian C, Hao F Z, Kai G and Liang L Z 2008 Catal. Commun. 9 1924;
37. Pilar F and Antonio G 2004 J. Mol. Catal., A: Chem. 214 137;
38. Shen J H, Wang H, Liu H C, Sun Y and Liu Z M 2008 J. Mol. Catal. A: Chem. 280 24
39. Gupta R, Gupta A K, Paul S and Kachroo P L 1995 Indian J. Chem. 34 61
40. Funiss B S, Hannford A J, Smith P W G Tatchell A R 2004 Vogel's Textbook of practical organic chemistry, fifth edition 19 1032;
41. Guantai, Kanyile Ncokazi E M, Timothy E J, Jiri Gut, Rosenthal, P J, Smith, P J and Kelly Chibale 2010 Bioorg. Med. Chem. 18 8243;
42. Ahmed Kamal S, Prabhakar M, Janaki Ramaiah P, Venkat Reddy, Ratna Reddy A, Mallareddy Nagula Shankaraiah T, Lakshmi Narayan Reddy S, Pushpavalli N C and Manika Pal Bhadra V L w2011 Eur. J. Med. Chem. 46 3820
43. Fun H K, Hemamalini M, Shanmugavelan P, Ponnuswamy A and Jagatheesan R 2011 Acta Cryst. E67 o2707
44. Fun H K, Hemamalini M, Shanmugavelan P, Ponnuswamy A and Jagatheesan R 2011 Acta Cryst. E67 o2776
45. Sundberg R J 1996 The Chemistry of Indoles, NewYork: Academic Press 113
46. Saxton J E 1997 Nat. Prod. Rep. 14 559;
47. Toyota M and Ihara N 1998 Nat. Prod. Rep. 15 327
48. Szmuszkovicz J 1957 J. Am. Chem. Soc. 79 2819;
49. Iqbal Z, Jackson AH, and Rao K R N 1988 Tetrahedron Lett. 29 2577;
50. Tahir R, Banert K, Solhy A, Sebt S. 2006 J. Mol. Catal. A. 39 246;
51. Zhou W, Xu L W, Yang L, Zhao P Q and Xia C G 2006 Eur. J. Org. Chem. (23) 5225
52. Zhan Z P and Lang K 2005 Synlett (10) 1551;
53. Yadav J S, Reddy B V S, Baishya G, Reddy K V and Narsaiah A V 2005 Tetrahedron 61 9541;
54. Zhan Z P, Yang R F and Lang K 2005 Tetrahedron Lett. 46 3859
55. Noland W E, Christensen G M, Sauer G L and Dutton G G S 1955 J. Am. Chem. Soc. 77 456
56. Harrington P and Kerr M A 1998 Can. J. Chem. 76 1256;
57. Loh T P and Wei L L 1998 Synlett (9) 975;
58. Loh T P, Pei J and Lin M 1996 Chem. Commun. (20) 2315;
59. Yadav J S, Abraham S, Reddy BVS and Sabitha G 2001 Synthesis. (14) 2165;
60. Bandini M, Cozzi PG, Giacomini M, Melchiorre P, Selva S and Umani-Ronchi A 2002 J. Org. Chem. 67 3700
61. Tahir R, Banert K, Solhy A and Sebti S 2006 J. Mol. Catal. A Chem. 246 39;
62. Ko S K Lin C C, Tu Z J, Wang Y F, Wang C C and Yao, C F 2006 Tetrahedron Lett. 47 487;
63. Bandini M, Cozzi P G, Giacomini M, Melchiorre P and Selva S 2002 J. Org. Chem. 67 3700;
64. Ji S J and Wang S Y 2005 Sonochem. 12 339;
65. Srivastava N and Banik B K 2003 J. Org. Chem. 68 2109;
66. Ekbote S S, Panda, A G, Bhor M D and Bhanage BM 2009 Catal. Commun. 10 1569;
67. Li D P, Guo Y C, Ding Y and Xiao W J 2006 Chem. Commun. 37 799