A robust one-pot synthesis of benzothiazoles from carboxylic acids including examples with hydroxyl and amino substituents

Tetrahedron Letters

Volumn 53, Issue 51, 2012, Pages 6950-6953

  Meghdadi, Soraia ^a   Amirnasr, Mehdi ^b   Ford, Peter C ^b  

^a ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

2 Aminothiophenol; Benzothiazole; Ionic liquid; Substituted carboxylic acid; Triphenyl phosphite

Indexed keywords

BENZOTHIAZOLE DERIVATIVE; CARBOXYLIC ACID; HYDROXYL GROUP; PHOSPHITE; TETRABUTYLAMMONIUM; TRIPHENYL PHOSPHITE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; ONE POT SYNTHESIS; REACTION TIME;

EID: 84869237289     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.10.035     Document Type: Article

References (47)

1. I. Hutchinson, S.A. Jennings, B.R. Vishnuvajjala, A.D. Westwell, and M.F.G. Stevens J. Med. Chem. 45 2002 744 747
2. S. Aiello, G. Wells, E.L. Stone, H. Kadri, R. Bazzi, D.R. Bell, M.F.G. Stevens, C.S. Matthews, and T.D. Bradshaw J. Med. Chem. 51 2008 5135 5239
3. V.R. Solomon, C. Hu, and H. Lee Bioorg. Med. Chem. 17 2009 7585 7592
4. L. Racane, M. Kralj, L. Suman, R. Stojković, V. Tralić-Kulenović, and G. Karminski-Zamola Bioorg. Med. Chem. 18 2010 1038 1044
5. S. Tzanopoulou, M. Sagnou, M. Paravatou-Petsotas, E. Gourni, G. Loudos, S. Xanthopoulos, D. Lafkas, H. Kiaris, A. Varvarigou, I.C. Pirmettis, M. Papadopoulos, and M. Pelecanou J. Med. Chem. 53 2010 4633 4641
6. W. Huang, and G.-F. Yang Bioorg. Med. Chem. 14 2006 8280 8285
7. C. Sheng, X. Che, W. Wang, S. Wang, Y. Cao, J. Yao, Z. Miao, and W. Zhang Eur. J. Med. Chem. 46 2011 1706 1712
8. P. Patel, J. Pillai, N. Darji, and B. Patel Int. J. Drug Res. Technol. 2 2012 170 176
9. S. Shafi, M.M. Alam, N. Mulakayala, C. Mulakayala, G. Vanaja, A.M. Kalle, R. Pallu, and M.S. Alam Eur. J. Med. Chem. 49 2012 324 333
10. S. Bondock, W. Fadaly, and M.A. Metwally Eur. J. Med. Chem. 44 2009 4813 4818
11. S. Saeed, N. Rashid, P.G. Jones, M. Ali, and R. Hussain Eur. J. Med. Chem. 45 2010 1323 1331
12. S.R. Nagarajan, G.A. De Crescenzo, D.P. Getman, H.-F. Lu, J.A. Sikorski, J.L. Walker, J.J. McDonald, K.A. Houseman, G.P. Kocan, N. Kishore, P.P. Mehta, C.L. Funkes-Shippy, and L. Blystone Bioorg. Med. Chem. 11 2003 4769 4777
13. S.L. Johnson, L.H. Chen, E. Barile, A. Emdadi, M. Sabet, H. Yuan, J. Wei, D. Guiney, and M. Pellecchia Bioorg. Med. Chem. 17 2009 3352 3368
14. K.M. Khan, F. Rahim, S.A. Halim, M. Taha, M. Khan, S. Perveen, M. Zaheer-ul-Haq, M.A. Mesaik, and M.I. Choudhary Bioorg. Med. Chem. 19 2011 4286 4294
15. L. Huang, T. Su, W. Shan, Z. Luo, Y. Sun, F. He, and X. Li Bioorg. Med. Chem. 20 2012 3038 3048
16. M. Ono, S. Hayashi, H. Kimura, H. Kawashima, M. Nakayama, and H. Saji Bioorg. Med. Chem. 17 2009 7002 7007
17. M.-C. Cui, Z.-J. Li, R.-K. Tang, and B.-L. Liu Bioorg. Med. Chem. 18 2010 2777 2784
18. M. Qureshi, Z. Khan, and S. Sundar Manoharan Chem. Phys. Lett. 473 2009 184
19. N.M. Shavaleev, R. Scopelliti, F. Gumy, and J.-C.G. Bünzli Inorg. Chem. 48 2009 2908
20. S.-G. Roh, Y.-H. Kim, K.D. Seo, D.H. Lee, H.K. Kim, Y.-I. Park, J.-W. Park, and J.-H. Lee Adv. Funct. Mater. 19 2009 1663
21. T. Iijima, A. Momotake, Y. Shinohara, T. Sato, Y. Nishimura, and T.J. Aria Phys. Chem. A 114 2010 1603
22. M.M.M. Rapso, M.C.R. Castro, A.M.C. Fonseca, P. Schellenberg, and M. Belsley Tetrahedron 67 2011 5189
23. K.C. Song, J.S. Kim, S.M. Park, K.-C. Chung, S. Ahn, and S.-K. Chang Org. Lett. 8 2006 3413
24. Haughland, R. P.; Zhang, Y.-Z.; Yue, S. T.; TerpetSching, E.; Olsen, N. A.; Naleway, J. J.; Larison, K. D.; Huang, Z. U.S. Patent 5,316,906, 1994; Chem. Abstr. 1994, 119, 198570.
25. T.-I. Kim, H.J. Kang, G. Han, S.J. Chung, and Y. Kim Chem. Commun. 2009 5895 5897
26. J.A. Seijas, M.P. Vazquez-Tato, M.R. Carballido-Reboredo, J. Crecente-Campo, and L. Romar-Lopez Synlett 2007 313 317
27. X. Wen, J. El Bakali, R. Deprez-Poulain, and B. Deprez Tetrahedron Lett. 53 2012 2440 2443
28. M.B. Maradolla, S.K. Allam, A. Mandha, and G.V.P. Ghandramouli Arkivoc xv 2008 42 46
29. S. Billeau, F. Chatel, M. Robin, R. Faure, and J.-P. Galy Magn. Reson. Chem. 44 2006 102 105
30. H. Sharghi, and O. Asemani Synth. Commun. 39 2009 860 867
31. A.K. Chakraborti, C. Selvam, J. Kaur, and S. Bhagat Synlett 2004 851 855
32. A.J. Blacker, M.M. Farah, M.I. Hall, S.P. Marsden, O. Saidi, and J.M.J. Williams Org. Lett. 11 2009 2039 2042
33. Y. Riadi, R. Mamouni, R. Azzalou, M.E. Haddad, S. Routier, G. Guillaumet, and S. Lazar Tetrahedron Lett. 52 2011 3492 3495
34. R.G. Kalkhambkar, and K.K. Laali Tetrahedron Lett. 53 2012 4212 4215
35. D. Ma, S. Xie, P. Xue, X. Zhang, J. Dong, and Y. Jiang Angew. Chem., Int. Ed. 48 2009 4222 4225
36. Y. Cheng, Y. Qu, and P. Li Org. Lett. 14 2012 98 101
37. C.W. Phoon, P.Y. Ng, A.E. Ting, S.-L. Yeo, and M.-M. Sim Bioorg. Med. Chem. Lett. 11 2001 1647 1650
38. S. Dey, A. Efimov, C. Giri, K. Rissanen, and H. Lemmetyinen Eur. J. Org. Chem. 2011 6226 6232
39. G.-W. Lin, Y. Wang, Q.-M. Jin, T.-T. Yang, J.-M. Song, Y. Lu, Q.-J. Huang, K. Song, J. Zhou, and T. Lu Inorg. Chim. Acta 382 2012 35 42
40. S. Meghdadi, K. Mereiter, A. Amiri, N.S. Mohammadi, F. Zamani, and M. Amirnasr Polyhedron 29 2010 2225 2231
41. S. Meghdadi, V. Mirkhani, and P.C. Ford Synth. Commun. 42 2012 246 250
42. V. Meghdadi, V. Mirkhani, and P.C. Ford ChemInform 43 2012 49
43. L.-H. Gao, M. Guan, K.-Z. Wang, L.-P. Jin, and C.-H. Huang Eur. J. Inorg. Chem. 2006 3731 3737
44. Fabrega, O.; James, A.; Salwatura, V. L.; Orenga, S.; Stanforth, S.P. PCT Int. WO 152306 A2, 2008; Chem. Abstr. 2008, 150, 50003.
45. M. Cellier, O.J. Fabrega, E. Fazackerley, A.L. James, S. Orenga, J.D. Perry, V.L. Salwatura, and S.P. Stanforth Bioorg. Med. Chem. 19 2011 2903 2910
46. A. Pla-Dalmau J. Org. Chem. 60 1995 5468 5473
47. C. Rodriguez-Rodriguez, N. Sánchez de Groot, A. Rimola, Á. Álvarez-Larena, V. Lloveras, J. Vidal-Gancedo, S. Ventura, J. Vendrell, M. Sodupe, and P. González-Duarte J. Am. Chem. Soc. 131 2009 1436 1451