SYNTHESIS OF NEW BENZOTHIAZOLYL-PHENOTHIAZINE DERIVATIVES

Authors

Keywords:

phenothiazine, benzothiazole, NMR

Abstract

A series containing 1-, 2-, 3- and 4-(benzothiazol-2yl)-10Hphenothiazine derivatives was advantageously prepared by the condensation of each corresponding phenothiazine-carbaldehyde regioisomer with 2-amino-benzenethiol. The reaction conditions were optimized and the structures of the new compounds were unambiguously assigned based on high resolution nuclear magnetic resonance spectroscopy and mass spectrometry.

References

J.K. Reichert, J. Lochtman, R. Miiller, I. Kanen, Jahrestagung der FG Wasserchemie in der GdCh, Badenweiler, 1993.

R.B. Spies, B.D. Andresen and D.W. Rice Jr., Nature, 1987, 327, 697.

I. Liska, E.R. Brouwer, A.G.L. Ostheimer, H. Lingeman, U.A.T. Brinkman, R.B. Geerdink and W.H. Mulder, Int. J. Environ. Anal. Chem., 1992, 47, 267.

P. Reddy, Y. Lin, H. Chang, Arcivoc., 2007, XVI, 113.

Y. Heo, Y. Song, B. Kim, J. Heo, Tetrahedron Lett., 2006, 47, 3091.

H. Sharghi, O. Asemani, Synth. Commun., 2009, 39, 860. (b) X. Wen, J. El Bakali, R. Deprez-Poulain, B. Deprez, Tetrahedron Lett., 2012, 53, 2440. (c) V.K. Tandon, M. Kumar, Tetrahedron Lett. 2004, 45, 4185. (d) K. Yamamoto, H. Watanabe, Chem. Lett. 1982, 1225.

A.J. Blacker, M.M. Farah, M.I. Hall, S.P. Marsden, O. Saidi, J.M. Williams,

J. Org. Lett., 2009, 11, 2039. (b) C. Mukhopadhyay, P.K. Tapaswi, Tetrahedron Lett., 2008, 49, 6237. (c) M.A. Chari, D. Shobha, T. Sasaki, Tetrahedron Lett., 2011, 52, 5575. (d) S.S. Patil, V.D. Bobade, Synth. Commun., 2010, 40, 206. (e) S.M. Inamdar, V.K. More, S.K. Mandal, Tetrahedron Lett., 2013, 54, 579.

S.P.G. Costa, A.M.F. Oliveira-Campos, J.A. Ferreira, G. Kirsch, J. Chem. Res. (S), 1997, 314, J. Chem. Res. (M), 1997, 9, 2001.

P. Saha, T. Ramana, N. Purkait, A.M. Ashif, R. Paul, T.J. Punniyamurthy, Org. Chem., 2009, 74, 8719. (b) G. Evindar, R.A. Batey, J. Org. Chem., 2006, 71, 1802. (c) D. Yang, H. Fu, L. Hu, Y. Jiang, Y. Zhao, J. Org. Chem., 2008, 73, 7841. (d) J. Peng, M. Ye, C. Zong, F. Hu, L. Feng, X. Wang, Y. Wang, C. Chen, J. Org. Chem., 2011, 76, 716. (e) E.A. Jaseer, D.J.C. Prasad, A. Dandapat, G. Sekar, Tetrahedron Lett., 2010, 51, 5009. (f) T. Itoh, T. Mase, Org. Lett., 2007, 9, 3687. (g) D. Ma, S. Xie, P. Xue, X. Zhang, J. Dong, Y. Jiang, Angew. Chem., Int. Ed., 2009, 48, 4222.

H. Wang, L. Wang, J. Shang, X. Li, H. Wang, J. Guia, A. Leiab, Chem. Commun., 2012, 48, 76.

T.B. Nguyen, L. Ermolenko, W.A. Dean, A. Al-Mourabit, J. Org. Lett., 2012, 14, 5948.

Y. Liao, H. Qi, S. Chen, P. Jiang, W. Zhou, G. Deng, J. Org.Lett., 2012, 14, 6004.

K. Sukanta, B. Koh, E.R. Biehl, J. Heterocycl.Chem., 2006, 43, 1609.

K. Sukanta, H. Zhang, E.R. Biehl, Heterocycles, 2005, 65, 2119.(b) L. Cai, X. Ji, Z. Yao, F. Xu, Q. Shen, Chin. J. Chem., 2011, 29, 1880.

Z.-X. Wang, H.-L. Qin, J. Heterocycl. Chem., 2005, 42, 1001. (b) M.S. Mayo, X. Yu, X. Zhou, X. Feng, Y. Yamamoto, M. Bao, Org. Lett., 2014, 16, 764.

A. Ignat, T. Lovasz, M. Vasilescu, E. Fischer-Fodor, C.B. Tatomir, C. Cristea, L. Silaghi-Dumitrescu, V. Zaharia, Arch. Pharm. Chem. Life Sci., 2012, 345, 574.

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Published

2015-06-30

How to Cite

BRÉM, B. ., GÁL, E. ., CRISTEA, C. ., GĂINĂ, L. ., GROZAV, A. ., ZAHARIA, V. ., & SILAGHI-DUMITRESCU, L. . (2015). SYNTHESIS OF NEW BENZOTHIAZOLYL-PHENOTHIAZINE DERIVATIVES. Studia Universitatis Babeș-Bolyai Chemia, 60(2), 371–378. Retrieved from https://studia.reviste.ubbcluj.ro/index.php/chemia/article/view/8457

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