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Chitosan-SO3H: A Green Approach to 2-Aryl/Heteroaryl Benzothiazoles under Solvent-Free Conditions at Room Temperature
Corresponding Author(s) : Surendra Bose Bathula
Asian Journal of Chemistry,
Vol. 30 No. 7 (2018): Vol 30 Issue 7
Abstract
An efficient green protocol have been developed for the synthesis of 2-aryl/heteroaryl benzothiazole derivatives by intramolecular cyclocondensation of 2-mercaptoaniline with various substituted aryl/heteroaryl aldehydes using chitosan-SO3H as an efficient biocompatible and reusable heterogenous solid acid catalyst in presence of air under solvent free conditions at room temperature. 1H NMR and 13C NMR spectra recorded are in agreement with the reported data.
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- E. Rodriguez, G.H.N. Towers and J.C. Mitchell, Phytochemistry, 15, 1573 (1976); https://doi.org/10.1016/S0031-9422(00)97430-2.
- (a) T.D. Bradshaw and A.D. Westwell, Curr. Med. Chem., 11, 1009 (2004); https://doi.org/10.2174/0929867043455530. (b) S.J. Hays, M.J. Rice, D.F. Ortwine, G. Johnson, R.D. Schwarz, D.K. Boyd, L.F. Copeland, M.G. Vartanian and P.A. Boxer, J. Pharm. Sci., 83, 1425 (1994); https://doi.org/10.1002/jps.2600831013. (c) C.J. Paget, K. Kisner, R.L. Stone and D.C. Delong, J. Med. Chem., 12, 1016 (1969); https://doi.org/10.1021/jm00306a011. (d) D. Kumar, M.R. Jacob, M.B. Reynolds and S.M. Kerwin, Bioorg. Med. Chem., 10, 3997 (2002); https://doi.org/10.1016/S0968-0896(02)00327-9. (e) D. Alagille, R.M. Baldwin and G.D. Tamagnan, Tetrahedron Lett., 46, 1349 (2005); https://doi.org/10.1016/j.tetlet.2004.12.111.
- (a) B.A. Tuylu, H.S. Zeytinoglu and I. Isikdag, Biologia, 62, 626 (2007); https://doi.org/10.2478/s11756-007-0122-4. (b) S.J. Choi, H.J. Park, S.K. Lee, S.W. Kim, G. Han and H.Y. Choo, Bioorg. Med. Chem., 14, 1229 (2006); https://doi.org/10.1016/j.bmc.2005.09.051. (c) A.L. Loaiza-Pe’rez, V. Trapani, C. Hose, S.S. Singh, J. Trepel, M.F.G. Stevens, T.D. Bradshaw and E.A. Sausville, Mol. Pharmacol., 61, 13 (2002); https://doi.org/10.1124/mol.61.1.13.
- A.W. Hofmann, Ber. Dtsch. Chem. Ges., 12, 1126 (1879); https://doi.org/10.1002/cber.187901201293.
- P. Jacobson and A. Frankenbacher, Ber. Dtsch. Chem. Ges., 24, 1400 (1891); https://doi.org/10.1002/cber.189102401247.
- V.J. Majo, J. Prabhakaran, J.J. Mann and J.S. Dileep Kumar, Tetrahedron Lett., 44, 8535 (2003); https://doi.org/10.1016/j.tetlet.2003.09.138.
- (a) R. Breslow, Acc. Chem. Res., 13, 170 (1980); https://doi.org/10.1021/ar50150a002. (b) J.H. Clark and D.J. Macquarrie, Green Chemistry and Technology, Blackwell, Abingdon (2002). (c) P. Gupta and S. Paul, Catal. Today, 236, 153 (2014); https://doi.org/10.1016/j.cattod.2014.04.010. (d) M. Lee, B.-Y. Chen and W. Den, J. Appl. Sci. (Faisalabad), 5, 1272 (2015); https://doi.org/10.3390/app5041272.
- (a) A. Loupy, F. Maurel and A. Sabatié-Gogová, Tetrahedron, 60, 1683 (2004); https://doi.org/10.1016/j.tet.2003.11.042. (b) B.K. Pchelka, A. Loupy and A. Petit, Tetrahedron, 62, 10968 (2006); https://doi.org/10.1016/j.tet.2006.08.067. (c) M.A.P. Martins, C.P. Frizzo, D.N. Moreira, L. Buriol and P. Machado, Chem. Rev., 109, 4140 (2009); https://doi.org/10.1021/cr9001098. (d) G.W.W. Cave, C.L. Raston and J.L. Scott, Chem. Commun., 21, 2159 (2001); https://doi.org/10.1039/b106677n. (e) K. Tanaka and F. Toda, Chem. Rev., 100, 1025 (2000); https://doi.org/10.1021/cr940089p.
- (a) M.G. Peter, eds.: S. De Baets, E. Vandamme and A. Steinbüchel, Chitin and Chitosan in Fungi, In: Polysaccharides II: Polysaccharides from Eukaryotes, Wiley-VCH, Weinheim, vol. 6, p. 123-132 (2002). (b) V.E. Tikhonov, E.A. Stepnova, V.G. Babak, I.A. Yamskov, J. PalmaGuerrero, H.-B. Jansson, L.V. Lopez-Llorca, J. Salinas, D.V. Gerasimenko, I.D. Avdienko and V.P. Varlamov, Carbohydr. Polym., 64, 66 (2006); https://doi.org/10.1016/j.carbpol.2005.10.021.
- (a) K. Khan and Z.N. Siddiqui, Ind. Eng. Chem. Res., 54, 6611 (2015); https://doi.org/10.1021/acs.iecr.5b00511. (b) B.V.S. Reddy, A. Venkateswarlu, G.N. Reddy and Y.V.R. Reddy, Tetrahedron Lett., 54, 5767 (2013); https://doi.org/10.1016/j.tetlet.2013.07.165. (c) J. Safari, Z. Zarnegar, M. Sadeghi and F. Azizi, Curr. Org. Chem., 20, 2926 (2016); https://doi.org/10.2174/1385272820666160805112208.
- G. Evindar and R.A. Batey, J. Org. Chem., 71, 1802 (2006); https://doi.org/10.1021/jo051927q.
- H. Deng, Z. Li, F. Ke and X. Zhou, Chem. Eur. J., 18, 4840 (2012); https://doi.org/10.1002/chem.201103525.
- A.-M. Osman and I. Bassiouni, J. Org. Chem., 27, 558 (1962); https://doi.org/10.1021/jo01049a051.
- H. Sharghi and O. Asemani, Synth. Commun., 39, 860 (2009); https://doi.org/10.1080/00397910802431214.
- Z. Duan, S. Ranjit and X. Liu, Org. Lett., 12, 2430 (2010); https://doi.org/10.1021/ol100816g.
- T. Itoh and T. Mase, Org. Lett., 9, 3687 (2007); https://doi.org/10.1021/ol7015737.
- J.K. Huang, J. Chan, Y. Chen, C.J. Borths, K.D. Baucom, R.D. Larsen and M.M. Faul, J. Am. Chem. Soc., 132, 3674 (2010); https://doi.org/10.1021/ja100354j.
- C. Praveen, K.H. Kumar, D. Muralidharan and P.T. Perumal, Tetrahedron, 64, 2369 (2008); https://doi.org/10.1016/j.tet.2008.01.004.
- Y. Sun, H. Jiang, W. Wu, W. Zeng and X. Wu, Org. Lett., 15, 1598 (2013); https://doi.org/10.1021/ol400379z.
- T. Yamamoto, K. Muto, M. Komiyama, J. Canivet, J. Yamaguchi and K. Itami, Chem. Eur. J., 17, 10113 (2011); https://doi.org/10.1002/chem.201101091.
- M. Kodomari, Y. Tamaru and T. Aoyama, Synth. Commun., 34, 3029 (2004); https://doi.org/10.1081/SCC-200026663.
- T.G. Deligeorgiev, Dyes Pigments, 12, 243 (1990); https://doi.org/10.1016/0143-7208(90)85016-H.
- P.B. Gorepatil, Y.D. Mane and V.S. Ingle, Synlett, 24, 2241 (2013); https://doi.org/10.1055/s-0033-1339758.
- (a) B.S. Bose, K. Mukkanti and H. Venkatasubramanian, Lett. Org. Chem., 14, 353 (2017); https://doi.org/10.2174/1570178614666170329151935. (b) B.S. Bose, K. Mukkanti and H. Venkatasubramanian, Der Pharma Chem., 6, 326 (2014).
References
E. Rodriguez, G.H.N. Towers and J.C. Mitchell, Phytochemistry, 15, 1573 (1976); https://doi.org/10.1016/S0031-9422(00)97430-2.
(a) T.D. Bradshaw and A.D. Westwell, Curr. Med. Chem., 11, 1009 (2004); https://doi.org/10.2174/0929867043455530. (b) S.J. Hays, M.J. Rice, D.F. Ortwine, G. Johnson, R.D. Schwarz, D.K. Boyd, L.F. Copeland, M.G. Vartanian and P.A. Boxer, J. Pharm. Sci., 83, 1425 (1994); https://doi.org/10.1002/jps.2600831013. (c) C.J. Paget, K. Kisner, R.L. Stone and D.C. Delong, J. Med. Chem., 12, 1016 (1969); https://doi.org/10.1021/jm00306a011. (d) D. Kumar, M.R. Jacob, M.B. Reynolds and S.M. Kerwin, Bioorg. Med. Chem., 10, 3997 (2002); https://doi.org/10.1016/S0968-0896(02)00327-9. (e) D. Alagille, R.M. Baldwin and G.D. Tamagnan, Tetrahedron Lett., 46, 1349 (2005); https://doi.org/10.1016/j.tetlet.2004.12.111.
(a) B.A. Tuylu, H.S. Zeytinoglu and I. Isikdag, Biologia, 62, 626 (2007); https://doi.org/10.2478/s11756-007-0122-4. (b) S.J. Choi, H.J. Park, S.K. Lee, S.W. Kim, G. Han and H.Y. Choo, Bioorg. Med. Chem., 14, 1229 (2006); https://doi.org/10.1016/j.bmc.2005.09.051. (c) A.L. Loaiza-Pe’rez, V. Trapani, C. Hose, S.S. Singh, J. Trepel, M.F.G. Stevens, T.D. Bradshaw and E.A. Sausville, Mol. Pharmacol., 61, 13 (2002); https://doi.org/10.1124/mol.61.1.13.
A.W. Hofmann, Ber. Dtsch. Chem. Ges., 12, 1126 (1879); https://doi.org/10.1002/cber.187901201293.
P. Jacobson and A. Frankenbacher, Ber. Dtsch. Chem. Ges., 24, 1400 (1891); https://doi.org/10.1002/cber.189102401247.
V.J. Majo, J. Prabhakaran, J.J. Mann and J.S. Dileep Kumar, Tetrahedron Lett., 44, 8535 (2003); https://doi.org/10.1016/j.tetlet.2003.09.138.
(a) R. Breslow, Acc. Chem. Res., 13, 170 (1980); https://doi.org/10.1021/ar50150a002. (b) J.H. Clark and D.J. Macquarrie, Green Chemistry and Technology, Blackwell, Abingdon (2002). (c) P. Gupta and S. Paul, Catal. Today, 236, 153 (2014); https://doi.org/10.1016/j.cattod.2014.04.010. (d) M. Lee, B.-Y. Chen and W. Den, J. Appl. Sci. (Faisalabad), 5, 1272 (2015); https://doi.org/10.3390/app5041272.
(a) A. Loupy, F. Maurel and A. Sabatié-Gogová, Tetrahedron, 60, 1683 (2004); https://doi.org/10.1016/j.tet.2003.11.042. (b) B.K. Pchelka, A. Loupy and A. Petit, Tetrahedron, 62, 10968 (2006); https://doi.org/10.1016/j.tet.2006.08.067. (c) M.A.P. Martins, C.P. Frizzo, D.N. Moreira, L. Buriol and P. Machado, Chem. Rev., 109, 4140 (2009); https://doi.org/10.1021/cr9001098. (d) G.W.W. Cave, C.L. Raston and J.L. Scott, Chem. Commun., 21, 2159 (2001); https://doi.org/10.1039/b106677n. (e) K. Tanaka and F. Toda, Chem. Rev., 100, 1025 (2000); https://doi.org/10.1021/cr940089p.
(a) M.G. Peter, eds.: S. De Baets, E. Vandamme and A. Steinbüchel, Chitin and Chitosan in Fungi, In: Polysaccharides II: Polysaccharides from Eukaryotes, Wiley-VCH, Weinheim, vol. 6, p. 123-132 (2002). (b) V.E. Tikhonov, E.A. Stepnova, V.G. Babak, I.A. Yamskov, J. PalmaGuerrero, H.-B. Jansson, L.V. Lopez-Llorca, J. Salinas, D.V. Gerasimenko, I.D. Avdienko and V.P. Varlamov, Carbohydr. Polym., 64, 66 (2006); https://doi.org/10.1016/j.carbpol.2005.10.021.
(a) K. Khan and Z.N. Siddiqui, Ind. Eng. Chem. Res., 54, 6611 (2015); https://doi.org/10.1021/acs.iecr.5b00511. (b) B.V.S. Reddy, A. Venkateswarlu, G.N. Reddy and Y.V.R. Reddy, Tetrahedron Lett., 54, 5767 (2013); https://doi.org/10.1016/j.tetlet.2013.07.165. (c) J. Safari, Z. Zarnegar, M. Sadeghi and F. Azizi, Curr. Org. Chem., 20, 2926 (2016); https://doi.org/10.2174/1385272820666160805112208.
G. Evindar and R.A. Batey, J. Org. Chem., 71, 1802 (2006); https://doi.org/10.1021/jo051927q.
H. Deng, Z. Li, F. Ke and X. Zhou, Chem. Eur. J., 18, 4840 (2012); https://doi.org/10.1002/chem.201103525.
A.-M. Osman and I. Bassiouni, J. Org. Chem., 27, 558 (1962); https://doi.org/10.1021/jo01049a051.
H. Sharghi and O. Asemani, Synth. Commun., 39, 860 (2009); https://doi.org/10.1080/00397910802431214.
Z. Duan, S. Ranjit and X. Liu, Org. Lett., 12, 2430 (2010); https://doi.org/10.1021/ol100816g.
T. Itoh and T. Mase, Org. Lett., 9, 3687 (2007); https://doi.org/10.1021/ol7015737.
J.K. Huang, J. Chan, Y. Chen, C.J. Borths, K.D. Baucom, R.D. Larsen and M.M. Faul, J. Am. Chem. Soc., 132, 3674 (2010); https://doi.org/10.1021/ja100354j.
C. Praveen, K.H. Kumar, D. Muralidharan and P.T. Perumal, Tetrahedron, 64, 2369 (2008); https://doi.org/10.1016/j.tet.2008.01.004.
Y. Sun, H. Jiang, W. Wu, W. Zeng and X. Wu, Org. Lett., 15, 1598 (2013); https://doi.org/10.1021/ol400379z.
T. Yamamoto, K. Muto, M. Komiyama, J. Canivet, J. Yamaguchi and K. Itami, Chem. Eur. J., 17, 10113 (2011); https://doi.org/10.1002/chem.201101091.
M. Kodomari, Y. Tamaru and T. Aoyama, Synth. Commun., 34, 3029 (2004); https://doi.org/10.1081/SCC-200026663.
T.G. Deligeorgiev, Dyes Pigments, 12, 243 (1990); https://doi.org/10.1016/0143-7208(90)85016-H.
P.B. Gorepatil, Y.D. Mane and V.S. Ingle, Synlett, 24, 2241 (2013); https://doi.org/10.1055/s-0033-1339758.
(a) B.S. Bose, K. Mukkanti and H. Venkatasubramanian, Lett. Org. Chem., 14, 353 (2017); https://doi.org/10.2174/1570178614666170329151935. (b) B.S. Bose, K. Mukkanti and H. Venkatasubramanian, Der Pharma Chem., 6, 326 (2014).