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Synthesis and Characterization of N,N',N'-Trichloro-6,7-epoxy-o-MeO-cinnamaldehyde Semicarbazone: A Potent Decontaminating Agent for Toxic Compounds
Corresponding Author(s) : Soram Ibomcha Singh
Asian Journal of Chemistry,
Vol. 27 No. 4 (2015): Vol 27 Issue 4
Abstract
A series of novel substituted cinnamaldehyde derivatives were designed and successively synthesized in three steps starting from o-methoxy-cinnamaldehyde semicarbazone to epoxy and finally to the N-chloro derivatives respectively, on the basis of semicarbazone based chemical decontaminants model to meet the structural requirements necessary for decontamination activity. Epoxidation with t-BuOOH in alkaline condition and chlorination using calcium hypochlorite were carried out. The structures of the synthesized compounds were confirmed on the basis of IR, Mass, 1H NMR spectral analysis. The presence of o-methoxy moiety in the system might play a significant role in the reactivity of the compound as a whole. It is well known that chloramines possess strong decontamination properties against toxic compounds and warfare agents. A more in-depth biological and chemical evaluation of the synthesized chloramine derivative(s) on toxic compounds of phosphorus and chemical warfare agents under suitable conditions requires a highly sophisticated laboratory.
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- W.O. Negherbon, A Handbook of Toxicology, Vol. III Insecticides; W.B. Saunders Company, London, pp. 536-569 (1959).
- V. Voronov and L. Fedorov, Moscom Khim. Zh., 7, 66 (1993).
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- 4 G.W. Wagner, G.W. Peterson and J.J. Mahle, Ind. Eng. Chem. Res., 51, 3598 (2012); doi:10.1021/ie202063p.
- M.J. Astle, Industrial Organic Nitrogen Compounds, Rienhold Publishing Corp., New York, pp. 188 (1961).
- A.E. Prill and D. Fisher, Contribs. Boyce Thompson Inst., 18, 299 (1956).
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- F.A. Carry and R.J. Sundberg, Advanced Organic Chemistry, Part B, Plenum Press, New York, edn 3, pp. 624-645 (1993).
- L.A. Paquette, Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, New York, Vol. 2, pp. 966-968 (1995).
- R. Zhongjiao, C. Weiguo, T. Weiqi and X. Jiajun, Synth. Commun., 31, 125 (2001); doi:10.1081/SCC-100000188.
- B.S.P. H. Beraldo and B.S.P. D. Gambinob, Mini Rev. Med. Chem., 4, 31 (2004); doi:10.2174/1389557043487484.
- R.F. Hudson, Structure and Mechanism in Organo-Phosphorus Chemistry, Academic Press, London, p. 6 (1965).
- S.I. Singh and S. Prabha, Orient. J. Chem., 24, 1131 (2008).
- S.I. Singh and S. Prabha, Asian J. Chem., 25, 4109 (2013); doi:10.14233/ajchem.2013.13754.
- R.L. Shriner and T.A. Turner, J. Am. Chem. Soc., 52, 1267 (1930); doi:10.1021/ja01366a073.
- F.A. Cotton and G. Wilkinson, Advanced Inorganic Chemistry, John-Wiley & Sons, Inc., New York, edn 6, pp. 457-459 (1999).
- M. Fieser and L. Fieser, Reagents for Organic Synthesis, John Wiley & Sons, New York, Vol. I, pp. 88 (1968).
- R.E. Kirk and D.F. Othmer, Encyclopedia of Chemical Technology, The Interscience Encyclopedia, Inc., New York, Vol. 3, p. 690 (1954).
- H. Remy, in ed.: J. Klienberg, Treatise on Inorganic Chemistry, Elsevier Publishing Co., New York, Vol. I, pp. 804-805 (1956).
- D.J. Blythin and E.S. Waight, J. Chem. Soc. B, 583 (1967); doi:10.1039/j29670000583.
- D. Becher, S.D. Sample and C. Djerassi, Chem. Ber., 99, 2284 (1966); doi:10.1002/cber.19660990728.
- R.M. Silverstein and F.X. Webster, Spectrometric Identification of Organic Compounds, John Wiley & Sons, Inc., edn 6, pp. 71-143 (2002).
- H. Yehia and A.B. Maki, Spectrochim. Acta A, 48, 1191 (1992); doi:10.1016/0584-8539(92)80132-G. (Eng.).
- D.B. Denney and M.J. Boskin, J. Am. Chem. Soc., 81, 6330 (1959); doi:10.1021/ja01532a055; D.B. Denney, J.J. Vill and M.J. Boskin, J. Am. Chem. Soc., 84, 3944 (1962); doi:10.1021/ja00879a028.
- R. Singh, P.K. Gutch, J. Acharya and S. Prabha, Indian J. Chem., 50B, 1504 (2011).
References
W.O. Negherbon, A Handbook of Toxicology, Vol. III Insecticides; W.B. Saunders Company, London, pp. 536-569 (1959).
V. Voronov and L. Fedorov, Moscom Khim. Zh., 7, 66 (1993).
3 T.J. Bandosz, M. Laskoski, J. Mahle, G. Mogilevsky, G.W. Peterson, J.A. Rossin and G.W. Wagner, J. Phys. Chem. C, 116, 11606 (2012); doi:10.1021/jp3028879.
4 G.W. Wagner, G.W. Peterson and J.J. Mahle, Ind. Eng. Chem. Res., 51, 3598 (2012); doi:10.1021/ie202063p.
M.J. Astle, Industrial Organic Nitrogen Compounds, Rienhold Publishing Corp., New York, pp. 188 (1961).
A.E. Prill and D. Fisher, Contribs. Boyce Thompson Inst., 18, 299 (1956).
H.S. Gatica, M.A. Frontera, O. Pieroni, M.A. Tomás and A. E. Zúñiga, J. Chromatogr. A, 369, 218 (1986); doi:10.1016/S0021-9673(00)90120-1.
F.A. Carry and R.J. Sundberg, Advanced Organic Chemistry, Part B, Plenum Press, New York, edn 3, pp. 624-645 (1993).
L.A. Paquette, Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, New York, Vol. 2, pp. 966-968 (1995).
R. Zhongjiao, C. Weiguo, T. Weiqi and X. Jiajun, Synth. Commun., 31, 125 (2001); doi:10.1081/SCC-100000188.
B.S.P. H. Beraldo and B.S.P. D. Gambinob, Mini Rev. Med. Chem., 4, 31 (2004); doi:10.2174/1389557043487484.
R.F. Hudson, Structure and Mechanism in Organo-Phosphorus Chemistry, Academic Press, London, p. 6 (1965).
S.I. Singh and S. Prabha, Orient. J. Chem., 24, 1131 (2008).
S.I. Singh and S. Prabha, Asian J. Chem., 25, 4109 (2013); doi:10.14233/ajchem.2013.13754.
R.L. Shriner and T.A. Turner, J. Am. Chem. Soc., 52, 1267 (1930); doi:10.1021/ja01366a073.
F.A. Cotton and G. Wilkinson, Advanced Inorganic Chemistry, John-Wiley & Sons, Inc., New York, edn 6, pp. 457-459 (1999).
M. Fieser and L. Fieser, Reagents for Organic Synthesis, John Wiley & Sons, New York, Vol. I, pp. 88 (1968).
R.E. Kirk and D.F. Othmer, Encyclopedia of Chemical Technology, The Interscience Encyclopedia, Inc., New York, Vol. 3, p. 690 (1954).
H. Remy, in ed.: J. Klienberg, Treatise on Inorganic Chemistry, Elsevier Publishing Co., New York, Vol. I, pp. 804-805 (1956).
D.J. Blythin and E.S. Waight, J. Chem. Soc. B, 583 (1967); doi:10.1039/j29670000583.
D. Becher, S.D. Sample and C. Djerassi, Chem. Ber., 99, 2284 (1966); doi:10.1002/cber.19660990728.
R.M. Silverstein and F.X. Webster, Spectrometric Identification of Organic Compounds, John Wiley & Sons, Inc., edn 6, pp. 71-143 (2002).
H. Yehia and A.B. Maki, Spectrochim. Acta A, 48, 1191 (1992); doi:10.1016/0584-8539(92)80132-G. (Eng.).
D.B. Denney and M.J. Boskin, J. Am. Chem. Soc., 81, 6330 (1959); doi:10.1021/ja01532a055; D.B. Denney, J.J. Vill and M.J. Boskin, J. Am. Chem. Soc., 84, 3944 (1962); doi:10.1021/ja00879a028.
R. Singh, P.K. Gutch, J. Acharya and S. Prabha, Indian J. Chem., 50B, 1504 (2011).