Ecofriendly and sustainable efficient synthesis of bis(indolyl)methanes based on recyclable Broønsted (CSA) or Lewis (ZrOCl2.8H 2O) acid catalysts

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

Volumn 50, Issue 11, 2011, Pages 1630-1636

  Mishra, Sarita ^a   Ghosh, Rina ^a  

^a JADAVPUR UNIVERSITY   (India)

Author keywords

Bis(indolyl)methane; CSA; Indole; ZrOCl2.8H2O

Indexed keywords

EID: 80755125272     PISSN: 03764699     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (58)

1. Sunderberg R J, The Chemistry of Indole (Academic press) 1970.
2. (a) Osawa T & Namiki M, Tetrahedron Lett, 24, 1983, 4719;
3. (b) Bell R, Carmelli S & Sar N, J Nat Prod, 57, 1994, 1587;
4. (c) Bifulco G, Bruno I, Riccio R, Lavayre J & Bourdy G, J Nat Prod, 58, 1995, 1254.
5. (a) Garbe T R, Kobayashi M, Shimizu N, Takesue N, Ozawa M & Yukawa H, J Nat Prod, 63, 2000, 596;
6. (b) Gillespie D E, Brady S F, Bettermann A D, Cianciotto N P, Liles M R, Rondon M R, Clardy J, Goodman R M & Handelsman J, Appl Environ Microbiol, 68, 2002, 4301.
7. Drasar B S & Hill M J, Human Intestinal Flora (Academic press, New York) 1974.
8. (a) Qin C, Morrow D, Stewart J, Spencer K, Porter W, Smith III R, Phillips T, Abdelrahim M, Samudio I & Safe S, Mol Cancer Ther, 3, 2004, 247;
9. (b) Contractor R, Samudio I J, Estrov Z, Harris D, McCubrey J A, Safe S H, Andreeff M & Konopleva M, Cancer Res, 65, 2005, 2890;
10. (c) Chintharlapalli S, Burghardt R, Papineni S, Ramaiah S, Yoon K & Safe S, J Biol Chem, 280, 2005, 24903.
11. Remers W A, Hetrocyclic Compounds, (Interscience Publishers, New York) 1972, p. 1.
12. Zeligs M A, J Med Food, 1, 1998, 67.
13. Martinez R, Espinosa A, Tarraga A & Molina P, Tetrahedron , 64, 2008, 2184.
14. (a) Xia M, Wang S -H & Yuan W -B, Synth Commun, 34, 2004, 3175;
15. (b) Chen D, Yu L, Wang P G, Tetrahedron Lett, 37, 1996, 4467;
16. (c) Nagarjan R, Perumal P T, Tetrahedron , 58, 2002, 1229;
17. (d) Mi X, Luo S, Hea J & Chenga J P, Tetrahedron Lett, 45, 2004, 4567.
18. (a) Babu G, Sridhar N & Perumal P T, Synth Commun, 30, 2000, 1609;
19. (b) Mo L -P, Chuan Z & Zhang H, Synth Commun, 35, 2005, 1997;
20. (c) Nagawade R R & Shinde D B, Bull Kor Chem Soc, 26, 2005, 1962;
21. (d) Selvam J J P, Srinivasulu M, Suryakiran N, Suresh V M, Reddy S & Venkateswarlu Y, Synth Commun, 38, 2008, 1760;
22. (e) Ji S J, Zhou M F, Gu D G, Jiang Z -Q, Loh T P, Eur J Org Chem, 2004, 1584;
23. (f) Zhang Z -H, Yin L & Wang Y -M, Synthesis, 2005 , 1949;
24. (g) 10 (g) Claudio C S, Samuel R M, Francieli M L & Eder J L, Gelson P, Tetrahedron Lett, 50, 2009, 6060.
25. Noland W E, Venkiteswaran M R, Richards C G, J Org Chem, 26, 1961, 4241.
26. Lee C -H & Lindsey J S, Tetrahedron, 50, 1994, 11427.
27. (a) Li J T, Dai H G, Xu W Z & Li T S, Ultrason Sonochem, 13, 2006, 24;
28. (b) Singh P R, Singh D U & Samant S D, Synth Commun, 35, 2005, 2133.
29. Azizian J, Teimouri F & Mohammadizadeh M R, Catal Commun, 8, 2007, 1117.
30. Azizi N, Torkian L & Saidi M R, J Mol Catal A: Chem, 275, 2007, 109.
31. Firouzabadi H, Iranpoor N, Jafarpour M, Ghaderi A, J Mol Catal A: Chem., 253, 2006, 249.
32. (a) Ramesh C, Banerjee J, Pal R & Das B, Adv Synth Catal, 345, 2003, 557;
33. (b) Bandagar B P, Patil A V & Kamble V T, Arkivoc , xvi, 2007, 252.
34. (c) Kamble V T, Kadam K R, Joshi N S & Muley D B, Catal Commun, 8, 2007, 498.
35. (a) Chakrabarty M & Sarkar S, Tetrahedron Lett, 43, 2002, 1351.
36. (b) Chakravarty M, Ghosh N, Basak R & Harigaya Y, Tetrahedron Lett, 43, 2002, 4075.
37. Bandgar B P & Shaikh K A, Tetrahedron Lett, 44, 2003, 1959.
38. Ramesh C, Ravindranath N & Das B, J Chem Res (S), 2003, 72.
39. Sharma G V M, Reddy J J, Lakshmi P S & Krishna P R, Tetrahedron Lett, 45, 2004, 7729.
40. (a) Ke B, Qin Y, Wang Y & Wang F, Synth Commun, 35, 2005, 1209;
41. (b) Feng X, Guan C & Zhao C, Synth Commun, 34, 2004, 487.
42. (a) Nadkarni S V, Gawande M B, Jayaram R V & Nagarkar J M, Cat Commun , 9, 2008, 1728;
43. (b) Satam J R, Parghi K D & Jayaram R V, Catal Commun, 9, 2008, 1071.
44. (a) Yadav J S, Reddy B V S & Sunitha S, Adv. Synth Catal, 345, 2003, 349;
45. (b) Dabiri M, Salehi P, Baghbanzadeh M, Shakuri M, Otokesh S, Ekrami T & Doosti R, J Iran Chem Soc, 4, 2007, 393;
46. (c) Kurosh R -M & Masoumeh S -K, Tetrahedron, 65, 2009, 8816.
47. (a) Firouzabadi H & Jafarpour M, J Iran Chem Soc, 5, 2008, 159;
48. (b) Zhang J-H & Li T-S, Curr Org Chem, 13, 2009, 1;
49. (c) Ghosh R, Maiti S, Chakraborty A, Chakraborty S & Mukherjee A K, Tetrahedron , 62, 2006, 4059;
50. (d) Mohammadpoor-Baltork I, Khosropour A R & Hojati S F, Catal Commun 8, 2007, 1865;
51. (e) Mantri K, Komura K & Sugi Y, Green Chem, 7, 2005, 677-682;
52. (f) Mantri K, Komura K & Sugi Y, Synthesis , 2005, 1939;
53. (g) Shi M, Cui S -C & Vin W -P, Eur J Org Chem, 2005, 2379;
54. (h) Hashemi M M, Eftekhari-sis B, Abdollahifar A & Khalili B, Tetrahedron, 62, 2006, 672;
55. (i) Moghaddam F M, Ismaili H, & Bardajee G R, Heteroatom Chem, 17, 2006, 136;
56. (j) Ghosh R, Maiti S, Chakraborty A, Chakraborty S & Mukherjee A K, Tetrahedron, 62, 2006, 4059;
57. (k) Ghosh R, Maiti S & Chakraborty A, Tetrahedron Lett, 46, 2005, 147.
58. Liao B-S, Chen J-T & Liu S-T, Synthesis, 2007, 3125.