Home Articles List Article Information
Iranian Journal of Catalysis
Journal Archive
Volume Volume 9 (2019)
Volume Volume 8 (2018)
Volume Volume 7 (2017)
Volume Volume 6 (2016)
Volume Volume 5 (2015)
Volume Volume 4 (2014)
Volume Volume 3 (2013)
Volume Volume 2 (2012)
Volume Volume 1 (2011)
Mirjalili, B., Bamoniri, A., Mirhoseini, M. (2016). One-pot synthesis of 1,3-benzo[d]thiazole derivatives promoted by Al(HSO4)3 under sonication conditions. Iranian Journal of Catalysis, 6(1), 23-27.
Bi Bi Fatemeh Mirjalili; Abdolhamid Bamoniri; Mohammad Ali Mirhoseini. "One-pot synthesis of 1,3-benzo[d]thiazole derivatives promoted by Al(HSO4)3 under sonication conditions". Iranian Journal of Catalysis, 6, 1, 2016, 23-27.
Mirjalili, B., Bamoniri, A., Mirhoseini, M. (2016). 'One-pot synthesis of 1,3-benzo[d]thiazole derivatives promoted by Al(HSO4)3 under sonication conditions', Iranian Journal of Catalysis, 6(1), pp. 23-27.
Mirjalili, B., Bamoniri, A., Mirhoseini, M. One-pot synthesis of 1,3-benzo[d]thiazole derivatives promoted by Al(HSO4)3 under sonication conditions. Iranian Journal of Catalysis, 2016; 6(1): 23-27.

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

Article 2, Volume 6, Issue 1, Winter 2016, Page 23-27  XML PDF (1.17 MB)
Document Type: Short Communications
Authors
Bi Bi Fatemeh Mirjalili email 1; Abdolhamid Bamoniri2; Mohammad Ali Mirhoseini1
1Department of Chemistry, College of Science, Yazd University, Yazd, PO Box 89195-741, I. R. Iran.
2Department 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
1; 3-Benzo[d]thiazole; Benzothiazoles; Al(HSO4)3; Aluminium hydrogen sulfate; 2- Aminotiophenol; Sonication conditions
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.

Statistics
Article View: 1,251
PDF Download: 1,269