Alum catalyzed simple and efficient synthesis of Bis(indolyl)methanes by ultrasound approach

Bulletin of the Korean Chemical Society

Volumn 30, Issue 4, 2009, Pages 825-828

  Sonar, Swapnil S ^a   Sadaphal, Sandip A ^a   Kategaonkar, Amol H ^a   Pokalwar, Rajkumar U ^a   Shingate, Bapurao B ^a   Shingare, Murlidhar S ^a  

^a DR BABASAHEB AMBEDKAR MARATHWADA UNIVERSITY   (India)

Author keywords

1H indole; Aldehydes ketones; Alum; Bis(indolyl)methanes; Ultrasound irradiation

Indexed keywords

1H-INDOLE; ALDEHYDES/KETONES; ALUM; BIS(INDOLYL)METHANES; ULTRASOUND IRRADIATION;

ACOUSTIC WAVES; CATALYSIS; CATALYSTS; IRRADIATION; METHANE; TOXIC MATERIALS; ULTRASONICS;

SULFATE MINERALS;

EID: 70349777320     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2009.30.4.825     Document Type: Article

References (57)

1. Sundberg, R. J. In The Chemistry of Indoles; Academic Press: New York, 1996; p 113.
2. Snieckus, V. In The Alkaloids; Academic Press: New York, 1968; Vol. 11, p 1.
3. nd ed.; Pergamom Press: New York, 1996; Vol. 2, p 211.
4. Morris, S. A.; Anderson, R. J. Tetrahedron 1990, 46, 715.
5. Bifulco, G.; Bruno, I.; Riccio, R.; Lavayre, J.; Bourdy, G. J. Nat. Prod. 1995, 58, 1254.
6. Miyake, F. Y.; Yakushijin, K.; Horne, D. A. Org. Lett. 2002, 4, 941.
7. Jiang, B.; Yang, C. G.; Wang, J. J. J. Org. Chem. 2002, 67, 1389.
8. Hong, C.; Firestone, G. L.; Bjeldanes, L. F. Biochem. Pharmacol. 2002, 63, 1085.
9. Ge, X.; Yannai, S.; Rennert, G.; Gruener, N.; Fares, F. A. Biochem. Biophys. Res. Commun. 1996, 228, 153.
10. Kamal, A.; Qureshi, A. A. Tetrahedron 1963, 19, 513.
11. Babu, G.; Sridhar, N.; Perumal, P. T. Synth. Commun. 2000, 30, 1609.
12. Yadav, J. S.; Reddy, B. V. S.; Murthy, V. S. R.; Kumar, G. M.; Madan, C. Synthesis 2001, 783.
13. Koshima, H.; Matsuaka, W. J. Heterocyclic Chem. 2002, 39, 1089.
14. Nagarajan, R.; Perumal, P. T. Synth. Commun. 2002, 32, 105.
15. Ramesh, C.; Banerjee, J.; Pal, R.; Das, B. Adv. Synth. Catal. 2003, 345, 557.
16. Ramesh, C.; Ravindranath, N.; Das, B. J. Chem. Res. Synop. 2003, 72.
17. Bandgar, B. P.; Shaikh, K. A. J. Chem. Res. Synop. 2004, 34.
18. Nagarajan, R.; Perumal, P. T. Chem. Lett. 2004, 33, 288.
19. Nagawade, R. R.; Shide, D. B. Bull. Korean Chem. Soc. 2005, 26, 12.
20. Nagawade, R. R.; Shinde, D. B. Acta Chin. Slov. 2006, 53, 210.
21. Zolfigol, M. A.; Salehi, P.; Shiri, M.; Tankouchian, Z. Catal. Commun. 2007, 8, 173l.
22. Hasaninejad, A.; Zare, A.; Sharghi, H.; Niknam, K.; Shekouhya, M. Arkivoc 2007, xiv, 39.
23. Srinivasa, A.; Varma, P. P.; Hulikal, V. Monat. Fur. Chemie. 2008, 139, 111.
24. Nezhad, A. K.; Parhami, A.; Zare, A.; Zare, A. R. M.; Hasaninejad, A.; Panahi, F. Synthesis 2008, 617.
25. Reddy, A. V.; Ravinder, R.; Reddy, V. L. N.; Goud, T. V.; Ravikanth, V.; Venkateseswarlu, Y. Synth. Commun. 2003, 33, 3687.
26. Karthik, M.; Tripathi, A. K.; Gupta, N. M.; Palanichamy, M.; Murugesan, V. Catal. Commun. 2004, 5, 371.
27. Chakrabarty, M.; Gosh, N.; Basak, R.; Harigaya, Y. Tetrahedron Lett. 2002, 43, 4075.
28. Pnieres-Carrillo, G.; Garcia-Estrada, J. G.; Gutierrez-Ramirez, J. L.; Alvarez-Toledano, C. Green Chem. 2003, 5, 337.
29. Yadav, J. S.; Reddy, B. V. S.; Sunitha, S. Adv. Synth. Catal. 2003, 345, 349.
30. Ji, S. J.; Zhou, M. F.; Gu, D. G.; Wang, S. Y.; Loh, T. P. Synlett 2003, 2077.
31. Ji, S. J.; Zhou, M. F.; Gu, D. G.; Jiang, Z. Q.; Loh, T. P. Eur. J. Org. Chem. 2004, 1584.
32. Sadaphal, S. A.; Sonar, S. S.; Shingare, M. S. Central Euro. J. Chem. 2008, 6, 622.
33. Chen, D.; Yu, L.; Wang, P. G. Tetrahedron Lett. 1996, 37, 4467.
34. Nagarajan, R.; Perumal, P. T. Tetrahedron 2002, 58, 1229.
35. Mi, X. L.; Luo, S. Z.; He, J. Q.; Cheng, J. P. Tetrahedron Lett. 2004, 45, 4567.
36. Feng, X. L.; Guan, C. J.; Zhao, C. X. Synth. Commun. 2004, 34, 487.
37. Wang, L. M.; Han, J. W.; Tian, H.; Sheng, J.; Fan, Z. Y.; Tang, X. P. Synlett 2005, 337.
38. Tanaka, K. F. Chem. Rev. 2000, 100, 1025.
39. Mason, T. J.; Lorimer, J. P. In Sonochemistry: Theory, Application and Uses of Ultrasound in Chemistry; John Wiley and Son: New York, 1988.
40. Suslick, K. S. In Ultrasound, its Chemical, Physical and Biological Effects; VCH: Weinheim, 1988.
41. Gaplovsky, A.; Gaplovsky, M.; Toma, S.; Luche, J. L. J. Org. Chem. 2000, 65, 8444.
42. Deshmukh, R. R.; Rajagopal, R.; Srinivasan, K. V. Chem. Commun. 2001, 1544.
43. Azizian, J.; Mohammadi, A. A.; Karimi, A. R.; Mohammadizadeh, M. R. J. Org. Chem. 2005, 70, 350.
44. Dabiri, M.; Salehi, P.; Otokesh, S.; Baghbanzadeh, M.; Kozehgary, G.; Mohammadi, A. A. Tetrahedron Lett. 2005, 46, 6123.
45. Azizian, J.; Mohammadi, A. A.; Karimi, A. R.; Mohammadizadeh, M. R. Applied Catalysis 2006, 300, 85.
46. Dabiri, M.; Baghbanzadeh, M.; Kiani, S.; Vakilzadeh, Y. Monatshefte Fur Chieme 2007, 138, 997.
47. Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Bahramnejad, M. Monatshefte Fur Chieme, 2007, 138, 1253.
48. Dabiri, M.; Baghbanzadeh, M.; Nikcheh, M. S.; Arzroomchilar, E. Bioorg. Med. Chem. Lett. 008, 18, 436.
49. Mahajan, D.; Nagvi, T.; Sharma, R. L.; Kapoor, K. K. Australian J. Chem. 2008, 61, 159.
50. Mohammadi, A. A.; Mivechi, M.; Kefayati, H. Monatshefte Fur Chieme 2008, 139, 935.
51. Pawar, S. S.; Dekhane, D. V.; Shingare, M. S.; Thore, S. N. Australian J. Chem. 2008, 61, 905.
52. Hangarge, R. V.; Sonwane, S. A.; Jarikote, D. V.; Shingare, M. S. Green Chem. 2001, 3, 310.
53. Hangarge, R. V.; Jarikote, D. V.; Shingare, M. S. Green Chem. 2002, 4, 266.
54. Madje, B. R.; Patil, P. T.; Shindalkar, S. S.; Benjamin, S. B.; Dongare, M. K.; Shingare, M. S. Catalysis Commun. 2004, 5, 353.
55. Pawar, S. S.; Dekhane, D. V.; Shingare, M. S.; Thore, S. N. Tetrahedron Lett. 2008, 49, 4252.
56. Pawar, S. S.; Uppalla, L. S.; Shingare, M. S.; Thore, S. N. Tetrahedron Lett. 2008, 49, 5858.
57. 3, 400 MHz) δ 5.89 (1H, s), 6.67 (2H, s), 7.09-7.58 (13H, m), 7.94 (2H, bs, NH). ES-MS: m/z 322 (M+1).