Synthesis, Characterization and Crystal Structure of 4-Dichloroacetyl-2,5-dimethyl-8-oxo-1,4-diazabicyclo[3.3.0]octane

Ying Fu; Zhao-Zheng Xu; Fei Ye

doi:10.14233/ajchem.2014.15959

Issue

Vol. 26 No. 10 (2014): Vol 26 Issue 10

Issue Published : May 10, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis, Characterization and Crystal Structure of 4-Dichloroacetyl-2,5-dimethyl-8-oxo-1,4-diazabicyclo[3.3.0]octane

https://doi.org/10.14233/ajchem.2014.15959

Ying Fu

College of Science, Northeast Agricultural University, Harbin 150030, Heilongjiang Province, P.R. China

Zhao-Zheng Xu

College of Science, Northeast Agricultural University, Harbin 150030, Heilongjiang Province, P.R. China

Fei Ye

College of Science, Northeast Agricultural University, Harbin 150030, Heilongjiang Province, P.R. China

Corresponding Author(s) : Fei Ye

yefei@neau.edu.cn

Asian Journal of Chemistry, Vol. 26 No. 10 (2014): Vol 26 Issue 10
Article Published : May 10, 2014

Abstract

4-Dichloroacetyl-2,5-dimethyl-8-oxo-1,4-diazabicyclo[3.3.0]octane was synthesized by cycloaddition and acylation reaction. The molecular structure was characterized by IR, NMR, MS, elemental analysis and further confirmed by X-ray diffraction analysis. The title compound, C₁₀H₁₄N₂O₂Cl₂, crystallized in the monoclinic P2₁/c space group with unit cell parameters a = 10.286(2) Å, b = 11.513(2) Å, c = 12.234(5) Å, Z = 4, V = 1223.5(6) Å³, Dc = 1.439 g/cm³, F (000) = 552, R₁ = 0.0405 and wR₂ = 0.1020. In the crystal structure, the molecule was linked through intermolecular C(7)-H(7)...O(2) hydrogen bond forming a one dimension chain conformation.

Keywords

Synthesis X-ray structure 4-Dichloroacetyl-2,5-dimethyl-8-oxo-1,4- diazabicyclo[3.3.0]octane

Fu, Y., Xu, Z.-Z., & Ye, F. (2014). Synthesis, Characterization and Crystal Structure of 4-Dichloroacetyl-2,5-dimethyl-8-oxo-1,4-diazabicyclo[3.3.0]octane. Asian Journal of Chemistry, 26(10), 2896–2898. https://doi.org/10.14233/ajchem.2014.15959

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References

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References

G.W. Ge, Z.Y. Qi, Z.G. Ni, Y.Z. Li, H.B. Du and X.Z. You, Inorg. Chem. Commun., 20, 228 (2012); doi:10.1016/j.inoche.2012.03.014.

S. Henke, A. Schneemann, A. Wutscher and R.A. Fischer, J. Am. Chem. Soc., 134, 9464 (2012); doi:10.1021/ja302991b.

T.G. Wang, Q. Hou, X.M. Wang, J.H. Yu and J.Q. Xu, J. Cluster Sci., 23, 527 (2012); doi:10.1007/s10876-012-0464-0.

S. Muthusamy, S.A. Babu and C. Gunanathan, Synth. Commun., 32, 3247 (2002); doi:10.1081/SCC-120014028.

H. Sajiki, Y. Iida, K. Ikawa, Y. Sawama, Y. Monguchi, Y. Kitade, Y. Maki, H. Inoue and K. Hirota, Molecules, 17, 6519 (2012); doi:10.3390/molecules17066519.

L. Brethous, N. Garcia-Delgado, J. Schwartz, S. Bertrand, D. Bertrand and J.L. Reymond, J. Med. Chem., 55, 4605 (2012); doi:10.1021/jm300030r.

A.A. Fedorova, E.P. Goncharova, E.I. Ryabchikova, V.V. Vlasov and M.A. Zenkova, FEBS Lett., 586, 1669 (2012); doi:10.1016/j.febslet.2012.04.047.

Q.S. Hossain, E. Ulziikhishig, K.K. Lee, H. Yamamoto and Y. Aniya, Toxicol. Appl. Pharmacol., 235, 77 (2009); doi:10.1016/j.taap.2008.11.016.

G.L. Lamoureux and D.G. Rusness, Z. Naturforsch., 46C, 882 (1991).

R.M. Devlin and I.I. Zbiec, Z. Naturforsch., 46c, 939 (1991).

F. Matloubi Moghaddam, G. Rezanejade Bardajee, H. Ismaili and S. Maryam Dokht Taimoory, Synth. Commun., 36, 2543 (2006); doi:10.1080/00397910600781448.

F. Ye, L. Yang, Y. Fu and S. Gao, Heterocycles, 83, 2607 (2011); doi:10.3987/COM-11-12326.

F. Ye, L. Yang, H.T. Li, Y. Fu and W.J. Xu, J. Heterocycl. Chem., 47, 229 (2010); doi:10.1002/jhet.289.

F. Ye, G.Y. Li, L. Ding, Y. Fu and Z.Y. Xing, Heterocycl. Commun., 19, 75 (2013); doi:10.1515/hc-2012-0174.

Y. Fu and F. Ye, Acta Crystallogr. E, 67, o2020 (2011); doi:10.1107/S1600536811027176.

S. Gao, L. X Zhao, F. Ye, Y. Fu and Z. Y. Xing, Acta Crystallogr. E, 68, o1982(2012); doi:10.1107/S1600536812024063.

Bruker, SMART (Version 5.628) and SAINT (Version 6.02), Bruker AXS Inc., Madison, Wisconsin, USA (1998).

G.M. Sheldrick, Acta Crystallogr. A, 64, 112 (2008); doi:10.1107/S0108767307043930.

Issue

Vol. 26 No. 10 (2014): Vol 26 Issue 10

Synthesis, Characterization and Crystal Structure of 4-Dichloroacetyl-2,5-dimethyl-8-oxo-1,4-diazabicyclo[3.3.0]octane

Corresponding Author(s) : Fei Ye

Abstract

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