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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Silica-supported Zinc Chloride (ZnCl2/SiO2)-induced Efficient Protocol for the Synthesis of N-sulfonyl imines and 2-Arylbenzothiazole

Author(s): Hanan A. Soliman*, Mahmoud El-Shahat and Abdel-Ghany Soliman

Volume 16, Issue 7, 2019

Page: [584 - 591] Pages: 8

DOI: 10.2174/1570178615666181025120307

Price: $65

Abstract

A straightforward strategy for the synthesis of N-sulfonyl imine derivatives from sulfonamides and aryl aldehydes utilizing Silica-supported zinc chloride (ZnCl2/SiO2, silzic) as a catalyst under solvent-free conditions has been developed. 2-Arylbenzothiazole derivatives were also synthesized by the reaction of 2-aminothiophenol with aryl aldehydes under the same conditions. This procedure has advantages of high yields, mild reaction condition, simple procedure, low cost, and simplicity of workup. The catalyst has the same efficiency on its reuse up to three times.

Keywords: N-sulfonyl imine, ZnCl2/SiO2, silzic, solvent-free, 2-arylbenzothiazole, aryl aldehydes.

Graphical Abstract
[1]
Jarrahpour, A.; Zarei, M. Molecules, 2006, 11, 49-58.
[2]
Yi, M.; Wong, H.N.C. J. Org. Chem., 2004, 69, 2892-2895.
[3]
Boger, D.L.; Corbett, W.L.; Curran, T.T.; Kasper, A.M. J. Am. Chem. Soc., 1991, 113, 1713-1729.
[4]
Nishikori, H.; Yoshihara, R.; Hosomi, A. Synlett, 2003, 4, 561-563.
[5]
Hori, R.; Aoayama, T.; Shoiri, T. Tetrahedron Lett, 2000, 41, 9455- 9458-9458.
[6]
Colpaert, F.; Mangelinckx, S.; Kimpe, N.D. Org. Lett., 2010, 12, 1904-1907.
[7]
Zhou, X-T.; Lin, Y-R.; Dai, L-X.; Sun, J.; Xia, L-J.; Tang, M-H. J. Org. Chem., 1999, 64, 1331-1334.
[8]
Hasaninejad, A.; Sharghi, H. Phosphorus Sulfur Silicon Relat. Elem., 2007, 182, 873.
[9]
Wu, X.F.; Bray, C.V.L.; Bechki, L.; Darcel, C. Tetrahedron, 2009, 65, 7380-7384.
[10]
Deng, G.S.; Zou, J.Y.; Sun, T.F. Chin. Chem. Lett., 2011, 22, 511-514.
[11]
Hasaninejad, A.; Zare, A. J. Sulfur Chem., 2007, 28, 357-364.
[12]
Hasaninejad, A.; Zare, A.; Sharghi, H.; Shekouhy, M. ARKIVOC, 2008, 11, 64-74.
[13]
Khalafi-Nezhad, A.; Parhami, A.; Zare, A.; Nasrolahi Shirazi, A.; Moosavi-Zare, A.R.; Hasaninejad, A.A. Can. J. Chem., 2008, 86, 456-461.
[14]
Hasaninejad, A.; Zare, A.; Moosavi-Zare, A. R.; Parhami, A.; Sharghi, H.; Khalafi-Nezhad, A. Phosphorus, Sulfur Silicon Relat. Elem., 2008, 183, 11, 2769.
[15]
Zare, A.; Moosavi-Zare, A.R.; Hasaninejad, A.; Parhami, A.; Khalafi-Nezhad, A.; Beyzavi, M.H. Synth. Commun., 2009, 39, 3156-3165.
[16]
Zolfigol, M.A.; Khazaei, A.; Moosavi-Zare, A.R.; Zare, A. J. Iran. Chem. Soc, 2010, 7, 646-651.
[17]
McFarlane, A.K.; Thomas, G.; Whiting, A.; McFarlane, A.K.; Thomas, G.; Whiting, A. Tetrahedron Lett., 1993, 34, 2379-2382.
[18]
Huang, D.; Wang, X.; Wang, X.; Chen, W.; Wang, X.; Hu, Y. Org. Lett., 2016, 18, 604-607.
[19]
Trost, B.M.; Marrs, C. J. Org. Chem., 1991, 56, 6468-6470.
[20]
Sisko, J.; Weinreb, S.M. J. Org. Chem., 1990, 55, 393-395.
[21]
Boger, D.L.; Corbett, W.L. J. Org. Chem., 1992, 57, 4777-4780.
[22]
Wolfe, J.P.; Ney, J.E. Org. Lett., 2003, 5, 4607-4610.
[23]
Zhang, G.; Xu, S.; Xie, X.; Ding, C.; Shan, S. RSC Adv., 2017, 7, 9431.
[24]
Patel, R.; Srivastava, V.P.L.; Yadav, D.S. Adv. Synth. Catal., 2010, 352, 1610-1614.
[25]
(a)Chawla, R.; Singh, A.K.; Yadav, L.D.S. Tetrahedron Lett., 2014, 55, 3553-3556.
(b)Shi, F.; Tse, M.K.; Zhou, S.; Pohl, M-M.; Radnik, J.; Hubner, S.; Jahnisch, K.; Bruckner, A.; Beller, M.J. Am. Chem. Soc, 2009, 131, 1775-1779.
[26]
Gupta, A.; Rawat, S.J. Chem. Pharm. Res., 2010, 2, 244.
[27]
Caleta, I.; Kralj, M.; Marjanovic, M.; Bertosa, B.; Tomic, S.; Pavlovic, G.; Pavelic, K.; Zamola, G.K. J. Med. Chem., 2009, 52, 1744-1756.
[28]
Bondock, S.; Fadaly, W.; Metwally, M. Eur. J. Med. Chem., 2010, 45, 3692-3701.
[29]
Neres, J.; Brewer, M.L.; Ratier, L.; Botti, H.; Buschiazzo, A.; Edwards, P.N.; Mortenson, P.N.; Charlton, M.H.; Alzari, P.M.; Frasch, A.C.; Bryce, R.A.; Douglas, K.T. Bioorg. Med. Chem. Lett., 2009, 19, 589-596.
[30]
Palmer, P.J.; Trigg, R.B.; Warrington, J.V. J. Med. Chem., 1971, 14, 248-251.
[31]
Rana, A.; Siddiqui, N.; Khan, S.A.; Haque, S.; Bhat, M. Eur. J. Med. Chem., 2008, 43, 1114-1122.
[32]
Serdons, K.; Verduyckt, T.; Vanderghinste, D.; Cleynhens, J.; Borghgraef, P.; Vermaelen, P.; Terwinghe, C.; Van Leuven, F.; Van Laere, K.; Kung, H.; Bormans, G. Bioorg. Med. Chem. Lett., 2009, 19, 602-605.
[33]
Boger, D.E. J. Org. Chem., 1978, 43, 2296-2297.
[34]
Rodionov, V.O.; Presolski, S.I.; Gardinier, S.; Lim, Y-H.; Finn, M.G. J. Am. Chem. Soc., 2007, 129, 12696-12704.
[35]
Bahrami, K.; Khodaei, M.; Naali, F. J. Org. Chem., 2008, 73, 6835-6837.
[36]
Pratap, U.R.; Mali, J.R.; Jawale, D.V.; Mane, R.A. Tetrahedron Lett., 2009, 50, 1352-1354.
[37]
Fan, X.; Wang, Y.; He, Y.; Zhang, X.; Wang, J. Tetrahedron Lett., 2010, 51, 3493-3496.
[38]
Evindar, G.; Batey, R.A. J. Org. Chem., 2006, 71, 1802-1808.
[39]
Wang, J.; Peng, F.; Jiang, J.; Lu, Z.; Wang, L.; Bai, J.; Pan, Y. Tetrahedron Lett., 2008, 49, 467-470.
[40]
Saha, P.; Ramana, T.; Purkati, N.; Ali, M.A.; Paul, R.; Punniyamurthy, T. J. Org. Chem., 2009, 74, 8719-8725.
[41]
Hutchinson, I.; Stevens, M.F.G.; Westwell, A.D. Tetrahedron Lett., 2000, 41, 425-428.
[42]
Bose, S.D.; Idrees, M.; Srikanth, B. Synthesis, 2007, 819-823.
[43]
Ma, D.; Lu, X.; Shi, L.; Zhang, H.; Jiang, Y.; Liu, X. Angew. Chem. Int. Ed., 2011, 50, 1118-1121.
[44]
Park, N.; Heo, Y.; Kumar, M.R.; Kim, Y.; Song, K.H.; Lee, S. Eur. J. Org. Chem., 2012, 10, 1984-1993.
[45]
Tanaka, K. Solvent-Free Organic Synthesis, Wiley-VCH, GmbH and KGaA, Weinheim. 2004.
[46]
Soliman, H.A.; Mubarak, A.Y.; Elmorsy, S.S. Chin. Chem. Lett., 2016, 27, 353-356.
[47]
Soliman, H.A.; Mubarak, A.Y. El- Mekabati, A.; Awad, H.M.; Elmorsy, S.S. Monatsh. Chem., 2016, 147, 809-816.
[48]
Soliman, H.A.; Mubarak, A.Y.; El-Mekabati, A.; Elmorsy, S.S. Chem. Sci. Trans., 2014, 3, 819.
[49]
Niralwad, K.S.; Shingate, B.B.; Shingare, M.S. Bull. Korean Chem. Soc., 2010, 31, 981-983.
[50]
Zhao, X.; Hu, H.; Zhang, F.; Zhang, Z. Appl. Catal. A Gen., 2014, 482, 258-265.
[51]
Zolfigol, M.A.; Tavasoli, M.; Moosavi-Zare, A.R.; Arghavani-Hadi, P.; Darvishi, G.; Zare, A.; Khakyzadek, V. RSC Adv., 2013, 3, 7692.
[52]
Khazaei, A.; Zolfigol, M.A.; Moosavi-Zare, A.R.; Zare, A.; Khojasteh, M.; Asgari, Z.; Khakyzadeh, V.; Khalafi-Nezhad, A. Catal. Commun., 2012, 20, 54-57.
[53]
Khazaei, A.; Moosavi-Zare, A.R.; Mohammadi, Z.; Zare, A.; Khakyzadeh, V.; Darvishi, G. RSC Adv, 2013, 3, 1323.
[54]
Soliman, H.A.; Khatab, T.K. Abdel-Megeid, F.M.E. Chin. Chem. Lett., 2016, 27, 1515-1518.
[55]
Soliman, H.A.; Abdel-Megeid, F.M.E.; Elmorsy, S.S. Org. Chem. Indian J., 2015, 11, 223-228.
[56]
Soliman, H.A.; Khatab, T.K. Egypt. J. Chem., 2014, 57, 129-142.
[57]
Khatab, T.K.; Mubarak, A.Y.; Soliman, H.A. J. Heterocycl. Chem., 2017, 54, 2463-2470.
[58]
Soliman, H.A.; Salama, T.A. Chin. Chem. Lett., 2013, 24, 404-406.
[59]
Upadhyaya, D.J.; Samant, S.D. Appl. Catal. A Gen., 2008, 340, 42-51.
[60]
Mirjalilia, B.F.; Bamonirib, A. Mirhoseinia. M.A. Iranian J. Catal., 2016, 6, 23-27.
[61]
Pranav, S.C.; Dinesh, R.G.; Tushar, V.G.; Rasika, C.T.; Nirmala, R.D. VRajashree, K. Acta Chim. Slov., 2011, 58, 367-371.
[62]
Maleki, B. Collect. Czech. Chem. Commun., 2011, 76, 27-37.
[63]
Khan, K.M.; Rahim, F.; Halim, S.A.; Taha, M.; Khan, M.; Perveen, S. Zaheer-ul-Haq; Mesaik, M.A.; Choudhary, M.I. Bioorg. Med. Chem., 2011, 19, 4286-4294.
[64]
Fawzia, Q.; Ramadan, A.M.; Kamal, U.S. Molecules, 2008, 13, 290.

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