FeCl3/ZnI2-catalyzed synthesis of benzo[D]imidazo[2,1-b]thiazole through aerobic oxidative cyclization between 2-aminobenzothiazole and ketone

Organic Letters

Volumn 16, Issue 23, 2014, Pages 6084-6087

  Mishra, Subhajit ^a   Monir, Kamarul ^a   Mitra, Shubhanjan ^a   Hajra, Alakananda ^a  

^a VISVA BHARATI UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOBENZOTHIAZOLE COMPOUND; BENZOTHIAZOLE DERIVATIVE; CHLORIDE; FERRIC CHLORIDE; FERRIC ION; IODIDE; KETONE; THIAZOLE DERIVATIVE; ZINC DERIVATIVE; ZINC IODIDE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; SYNTHESIS;

BENZOTHIAZOLES; CATALYSIS; CHLORIDES; CYCLIZATION; FERRIC COMPOUNDS; IODIDES; KETONES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; THIAZOLES; ZINC COMPOUNDS;

EID: 84916236096     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5028893     Document Type: Article

References (42)

1. Cremlyn, R. J. An Introduction to Organosulfur Chemistry; John Wiley & Sons: Chichester, 1996.
2. Hulten, J.; Bonham, N. M.; Nillroth, U.; Hansson, T.; Zuccarello, G.; Bouzide, A.; Aaqvist, J.; Classon, B.; Danielson, H. J. Med. Chem. 1997, 40, 885
3. Dauben, P.; Dodd, R. H. Org. Lett. 2000, 2, 2327
4. Katritzky, A. R.; Wu, J.; Rachwal, S.; Rachwal, B.; Macomber, D. W.; Smith, T. P. Org. Prep. Proced. 1992, 24, 463
5. Greig, I. R.; Tozer, M. J.; Wright, P. T. Org. Lett. 2001, 3, 369
6. Matthew, D. M.; Joseph, M. D.; Paul, R. H. Chem. Rev. 2004, 104, 2239
7. Dawson, P. E.; Muir, T. W.; Lewis, C. I.; Kent, S. B. H. Science 1994, 266, 776
8. Farag, A. M.; Mayhoub, A. S.; Barakat, S. E.; Bayomi, A. H. Bioorg. Med. Chem. 2008, 16, 4569
9. Al-Tel, T. H.; Al-Qawasmeh, R. A.; Zaarour, R. Eur. J. Med. Chem. 2011, 46, 1874
10. Furlan, A.; Colombo, F.; Kover, A.; Issaly, N. Eur. J. Med. Chem. 2012, 47, 239
11. Andreani, A.; Burnelli, S.; Granaiola, M.; Leoni, A. J. Med. Chem. 2008, 51, 809
12. Andreani, A.; Granaiola, M.; Locatelli, A.; Morigi, R. J. Med. Chem. 2012, 55, 2078
13. Andreani, A.; Burnelli, S.; Granaiola, M.; Leoni, A. J. Med. Chem. 2008, 51, 7508
14. Trapani, G.; Franco, M.; Latrofa, A.; Reho, A.; Liso, G. Eur. J. Pharm. Sci. 2001, 14, 209
15. Ager, I. R.; Barnes, A. C.; Danswan, G. W.; Hairsine, P. W. J. Med. Chem. 1988, 31, 1098
16. Palkar, M.; Noolvi, M.; Sankangoud, R.; Maddi, V. Arch. Pharm. Chem. Life Sci. 2010, 343, 353
17. Blackburn, C.; Duffey, M. O.; Gould, A. E.; Kulkarni, B. Bioorg. Med. Chem. Lett. 2010, 20, 4795
18. Andreani, A.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R. Eur. J. Med. Chem. 2011, 46, 4311
19. Yousefi, B. H.; Manook, A.; Drzezga, A.; Reutern, B. J. Med. Chem. 2011, 54, 949
20. Alagille, D.; DaCosta, H.; Baldwin, R. M.; Tamagnan, G. D. Bioorg. Med. Chem. Lett. 2011, 21, 2966
21. Yousefi, B. H.; Drzezga, A.; Reutern, B.; Manook, A. ACS Med. Chem. Lett. 2011, 2, 673
22. Mir, N. A.; Shah, T. A.; Ahmed, S.; Muneer, M.; Rath, N. P.; Ahmad, M. Tetrahedron Lett. 2014, 55, 1706
23. Kumbhar, V. V.; Hangirgekar, S. P.; Wadwale, N. B. Der Pharma Chem. 2013, 5, 274
24. Zhang, X.; Jia, J.; Ma, C. Org. Biomol. Chem. 2012, 10, 7944
25. Wu, Z.; Huang, Q.; Zhou, X.; Yu, L.; Li, Z.; Wu, D. Eur. J. Org. Chem. 2011, 5242
26. Kumbhare, R. M.; Kumar, K. V.; Ramaiah, M. J.; Dadmal, T.; Pushpavalli, S.N.C.V.L.; Mukhopadhyay, D.; Divya, B.; Dev, T. A.; Kosurkar, U.; Pal-Bhadra, M. Eur. J. Med. Chem. 2011, 46, 4258
27. Christodoulou, M. S.; Colombo, F.; Passarella, D.; Ieronimo, G.; Zuco, V.; De Cesare, M.; Zunino, F. Bioorg. Med. Chem. 2011, 19, 1649
28. Bakherad, M.; Nasr-Isfahani, H.; Keivanloo, A.; Sang, G. Tetrahedron Lett. 2008, 49, 6188
29. Guchhait, S. K.; Chaudhary, V. Org. Biomol. Chem. 2014, 12, 669
30. Louillat, M.-L.; Patureau, F. W. Chem. Soc. Rev. 2014, 43, 901
31. Shi, Z. Z.; Zhang, C.; Tang, C. H.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3381
32. Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439
33. Punniyamurthy, T.; Velusamy, S.; Iqbal, J. Chem. Rev. 2005, 105, 2329
34. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
35. Campbell, A. N.; Stahl, S. S. Acc. Chem. Res. 2012, 45, 851
36. Monir, K.; Bagdi, A. K.; Ghosh, M.; Hajra, A. Org. Lett. 2014, 16, 4630
37. Santra, S.; Mitra, S.; Bagdi, A. K.; Majee, A.; Hajra, A. Tetrahedron Lett. 2014, 55, 5151
38. Monir, K.; Bagdi, A. K.; Mishra, S.; Majee, A.; Hajra, A. Adv. Synth. Catal. 2014, 356, 1105
39. Bagdi, A. K.; Rahman, M.; Santra, S.; Majee, A.; Hajra, A. Adv. Synth. Catal. 2013, 355, 1741
40. Santra, S.; Bagdi, A. K.; Majee, A.; Hajra, A. Adv. Synth. Catal. 2013, 355, 1065
41. Stasyuk, A. J.; Banasiewicz, M.; Cyrański, M. K.; Gryko, D. T. J. Org. Chem. 2012, 77, 5552
42. Zhang, Y.; Chen, Z.; Wu, W.; Zhang, Y.; Su, W. J. Org. Chem. 2013, 78, 12494