One-pot synthesis of 1,3-benzo[d]thiazole derivatives promoted by Al(HSO4)3 under sonication conditions

Document Type : Short Communications

Authors

1 Department of Chemistry, College of Science, Yazd University, Yazd, PO Box 89195-741, I. R. Iran.

2 Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, I. R. Iran.

Abstract

The presence of an imidazole ring in natural products and pharmacologically active compounds has instituted a diverse array of synthetic approaches to these heterocycles. Very recently, we among many others have demonstrated that heterogeneous reagent systems have many advantages such as simple experimental procedures, mild reaction conditions and minimization of chemical wastes as compared to the liquid phase counterparts. Thus, inorganic acidic salts such as Al(HSO4)3, Mg(HSO4)2 and Zr(HSO4)4 could be recommended for above mentioned purposes. Al(HSO4)3 is an efficient, readily available and cheap catalyst for thesynthesis of 1,3-benzo[d]thiazole derivatives by condensation of 2-aminothiophenol and aldehydesunder sonication conditions.This protocol is very simple with easy workup and good to excellent yieldsof products.

Keywords

References

[1] X.Y. Zhu, J.R. Etukala, S.V.K. Eyunni, V. Setola, B.L. Roth, S.Y. Ablordeppey, Eur. J. Med. Chem. 53 (2012) 124-132.
[2] P. Xiang, T. Zhou, L. Wang, C.Y. Sun, J. Hu, Y.L. Zhao, L. Yang, Molecules 17 (2012) 873-883.
[3] D.T.K. Oanh, H.V. Hai, S.H. Park, H.-J. Kim, B.-W. Han, H.-S. Kim, J.-T. Hong, S.-B. Han, V.T.M. Hue, N.-H. Nam, Bioorg. Med. Chem. Lett. 21 (2011) 7509-7512.
[4] P. Ravi Prasad, S.D. Shinde, G.S. Waghmare, V. Lakshma Naik, K. Bhuvaneswari, S.V. Kuberkar, J. Chem. Pharm. Res. 3 (2011) 20-27.
[5] L.B. Labhsetwar, G.R. Shendarkar, S.V. Kuberkar, J. Pharm. Res. Health Care 2 (2010) 273-278.
[6] D. Havrylyuk, L. Mosula, B. Zimenkovsky, O. Vasylenko, A. Gzella, R. Lesyk, Eur. J. Med. Chem. 45 (2010) 5012-5021.
[7] R.M. Kumbhare, K. Vijay Kumar, M. Janaki Ramaiah, T. Dadmal, S.N.C.V.L. Pushpavalli, D. Mukhopadhyay, B. Divya, T. Anjana Devi, U. Kosurkar, M. Pal-Bhadra, Eur. J. Med. Chem. 46 (2011) 4258-4266.
[8] V.N. Telvekar, V.K. Bairwa, K. Satardekar, A. Bellubi, Bioorg. Med. Chem. Lett. 22 (2012) 649-652.
[9] S. Premlata, G. S. Verma, Seth, Res. J. Pharm. Biol. Chem. Sci. 3 (2012) 435-443.
[10] M. Amir, S.A. Javed, M.Z. Hassan, Med. Chem. Res. 21 (2012) 1261-1270.
[11] M. Palkar, M. Noolvi, R. Sankangoud, V. Maddi, A. Gadad, L.V.G. Nargund, Arch. der Pharm. 343 (2010) 353-359.
[12] S. Shafi, M. Mahboob Alam, N. Mulakayala, C. Mulakayala, G. Vanaja, A.M. Kalle, R. Pallu, M.S. Alam, Eur. J. Med. Chem. 49 (2012) 324-333.
[13] P. Zhao, F. Wang, W. Huang, Q. Chen, Z. Liu, Chin. J. Org. Chem. 30 (2010) 1567-1573.
[14] K.K. Sethi, S.M. Verma, N. Prasanthi, M.M. Annapurna, Lett. Drug Des. Discovery 8 (2011) 774-777.
[15] R.M. Kumbhare, T. Dadmal, U. Kosurkar, V. Sridhar, J.V. Rao, Bioorg. Med. Chem. Lett. 22 (2012) 453-455.
[16] C. Praveen, A. Nandakumar, P. Dheenkumar, D. Muralidharan, P.T. Perumal, J. Chem. Sci. 124 (2012) 609-624.
[17] R. Priyadharsini, A. Jerad Suresh, M. Sathish, S. Kavitha, C. Selvin Thanuja, Inter. J. Pharm. Pharm. Sci. 4 (2012) 574-584.
[18] M. Frohn, V.J. Cee, B.A. Lanman, A.J. Pickrell, J. Golden, D. Rivenzon-Segal, S. Middleton, M. Fiorino, H. Xu, M. Schrag, Y. Xu, M. McElvain, K. Muller, J. Siu, R. Bürli, Bioorg. Med. Chem. Lett. 22 (2012) 628-633.
[19] M. Karle, W. Knecht, Y. Xue, Bioorg. Med. Chem. Lett. 22 (2012) 4839-4843.
[20] F. Firooznia, A.W. Cheung, J. Brinkman, J. Grimsby, M.L. Gubler, R. Hamid, N. Marcopulos, G. Ramsey, J. Tan, Y. Wen, R. Sarabu, Bioorg. Med. Chem. Lett. 21 (2011) 1933-1936.
[21] N. Kumar, A.K. Tiwari, D. Kakkar, N. Saini, M. Chand, A.K. Mishra, Cancer Biother. Radiopharm. 25 (2010) 571-575.
[22] K.M. Khan, F. Rahim, S.A. Halim, M. Taha, M. Khan, S. Perveen, H. Zaheer Ul, M.A. Mesaik, M. Iqbal Choudhary, Bioorg. Med. Chem. 19 (2011) 4286-4294.
[23] Y. Yang, L. Tao, Y. Wu, C. Shi, Y. Zhang, Acta Energ. Sol. Sin. 33 (2012) 1-4.
[24] W. Sun, W. Li, J. Li, J. Zhang, L. Du, M. Li, Tetrahedron Lett. 53 (2012) 2332-2335.
[25] S. Stefansson, D.L. Adams, C.M. Tang, BioTechniques (2012) 1-6.
[26] M.-C. Cui, Z.-J. Li, R.-K. Tang, B.-L. Liu, Bioorg. Med. Chem. 18 (2010) 2777-2784.
[27] W.-P. Hu, Y.-K. Chen, C.-C. Liao, H.-S. Yu, Y.-M. Tsai, S.-M. Huang, F.-Y. Tsai, H.-C. Shen, L.-S. Chang, J.-J. Wang, Bioorg. Med. Chem. 18 (2010) 6197-6207.
[28] J. Qi, M.S. Han, C.H. Tung, Bioorg. Med. Chem. Lett. 22 (2012) 1747-1749.
[29] S.T. Ha, K.L. Foo, H.C. Lin, M.M. Ito, K. Abe, K. Kunbo, S.S. Sastry, Chinese Chem. Lett. 23 (2012) 761-764.
[30] G.K. Dutta, S. Guha, S. Patil, Org. Electron. 11 (2010) 1-9.
[31] S. Nadeem, M.A. Munawar, S. Ahmad, M. Smiglak, D.M. Drab, K.I. Malik, R. Amjad, C.M. Ashraf, R.D. Rogers, Arkivoc 2010 (2010) 19-37.
[32] C. Siddappa, V. Kambappa, M. Umashankara, K.S. Rangappa, Tetrahedron Lett. 52 (2011) 5474-5477.
[33] S. Meghdadi, M. Amirnasr, P.C. Ford, Tetrahedron Lett. 53 (2012) 6950-6953.
[34] S.S. Katkar, P.H. Mohite, L.S. Gadekar, K.N. Vidhate, M.K. Lande, Chinese Chem. Lett. 21 (2010) 421-425.
[35] F.M. Moghaddam, G.R. Bardajee, H. Ismaili, S.M.D. Taimoory, Synth. Commun. 36 (2006) 2543-2548.
[36] K.R. Kumar, P.V.V. Satyanarayana, B. Srinivasa Reddy, J. Chem. 2013 (2013) 1-10.
[37] M. Kodomari, Y. Tamaru, T. Aoyama, Synth. Commun. 34 (2004) 3029-3036.
[38] N. Azizi, A. Khajehamiri, M. M. Hashemi, R. Baghi, M. Bolourtchian, Monatsh. Chem. 140 (2009) 1471-1473.
[39] S. C. Pranav, R. G. Dinesh, V. G. Tushar, C. T. Rasika, R. D. Nirmala, V. K. Rajashree. Acta Chim. Slov. 58 (2011) 367-371.
[40] A. Ben-Alloum, S. Bakkas, M. Soufiaoui Tetrahedron Lett. 38 (1997) 6395-6396.
[41] R. S. Kenny, U. C. Mashelkar, J. Heterocycl. Chem. 43 (2006) 1367-1369.
[42] Q. Fawzia Al, A. M. Ramadan, U. S. Kamal Molecules 13 (2008) 2908-2914.
[43] B. Maleki Collect. Czech. Chem. Commun. 76 (2011) 27-37.
[44] P. Salehi, M. M. Khodaei, M.A. Zolfigol, S. Sirouszadeh. Bull. Chem. Soc. Jpn. 76 (2003) 1863-1864.
[45] H. R. Shaterian, M. Ghashang, N. Mir, Arkivoc XV (2007) 1-10.
[46] F. Shirini, M. A. Zolfigol, M. Abedini, Monatsh. Chem. 135 (2004) 279-282.
[47] F. Shirini, M. A. Zolfigol, M. Abedini, P. Salehi Bull. Korean Chem. Soc. 24 (2003) 1683-1685.
[48] F. Shirini, M. A. Zolfigol, M. Abedini, P. Salehi Mendeleev Commun. 13 (2003) 265-266.
[49] K.S. Niralwad, B.B. Shingate, M.S. Shingare Bull. Korean Chem. Soc. 31 (2010) 981-983.
[50] K.M. Khan, F. Rahim, S.  Ahsanhalim, M. Taha, M. Khan, S. Perveen, Z.L. Haq, M.A. Mesaik, M.I. Choudhary, Bioorg. Med. Chem. 19 (2011) 4286-4294.
[51] T.G. Deligeorgiev, Dyes Pigm. 12 (1990) 243-248.
[52] A. Cerniani, R. Passerini J. Chem. Soc. (1954) 2261-2264.

Files

Share

How to cite

Statistics