Synthesis and Spectral Characterization of Some New Substituted Bis-spirocyclohexanones Derived from Acetone

Authors

  • Mohammed S. Hussein Department of Chemistry, Faculty of Science, University of Zakho, Kurdistan Region - Iraq - (mohammed.huseein@uoz.edu.krd)
  • Abdul Wahab J. Al-Hamdany Department of Chemistry, College of Science, University of Mosul, Mosul, Iraq - (ajalhamadany@yahoo.com)
  • Rana A. Saeed Department of Pharmacy, Technical InstituteNorthern Technical University, Mosul, Iraq - (rana.al_alaf@yahoo.com)

DOI:

https://doi.org/10.25271/sjuoz.2018.6.4.548

Keywords:

Anthrone, spirocyclohexanones, Michael addition

Abstract

Diarylidene acetones (DAA) (1-5) had been prepared by the condensation of acetone with substituted benzaldehydes via Claisen-Schmidt reaction, DAA’s brought to condense with anthrone to afford the title compounds (6-10) through Michael addition. The structures of the products were suggested in the light of spectral data (UV, IR, 1H&13C-NMR).

Author Biographies

Mohammed S. Hussein, Department of Chemistry, Faculty of Science, University of Zakho, Kurdistan Region - Iraq - (mohammed.huseein@uoz.edu.krd)

Department of Chemistry, Faculty of Science, University of Zakho, Kurdistan Region - Iraq - (mohammed.huseein@uoz.edu.krd)

Abdul Wahab J. Al-Hamdany, Department of Chemistry, College of Science, University of Mosul, Mosul, Iraq - (ajalhamadany@yahoo.com)

Department of Chemistry, College of Science, University of Mosul, Mosul, Iraq - (ajalhamadany@yahoo.com)

 

Rana A. Saeed, Department of Pharmacy, Technical InstituteNorthern Technical University, Mosul, Iraq - (rana.al_alaf@yahoo.com)

Department of Pharmacy, Technical InstituteNorthern Technical University, Mosul, Iraq - (rana.al_alaf@yahoo.com)

References

A. A. Raj, and R. Raghnathan, “Synthesis of spiropyrrolidine via formal [3,2]cycloaddition of unusual enones and cis 3-benzoy l-1-cyclohexy l-2- phenylaziridine,” Tetrahedron, vol. 59, pp. 2907-2911, 2003.
A. Dandia, R. Singh, S. Khaturia, C. Merienne, G. Morgant, and A. Loupy, “Efficient microwave enhanced regioselective synthesis of a series of benzimidazolyl/triazolyl spiro[indole-thiazolidinones] as potent antifungal agents and crystal structure of spiro[3H-indole-3,2'- thiazolidine]-3'(1,2,4-triazol-3-yl)-2,4'(1H)-dione,” Bioorg. Med. Chem., vol. 14, pp. 2409–2417, 2006.
A. J. Al-Hamdany, M. S. Al-Jawady, R. A. Saeed, “Synthesis and Spectral Charactrization of Some Pyrimidinones,” Raf. J. Sci., vol. 25(3), pp. 16-23, 2014.
A. Scala, M. Cordaro, G. Grassi, A. Piperno, and G. Barberi, “Direct synthesis of C3-mono-functionalized oxindoles from N-unprotected 2-oxindole and their antileishmanial activity,” Bioorg. & Med. Chem., vol. 22, pp.1063–1069,2014.
A. Srikrishna and B. Vasantha Lakshmi, “Construction of vicinal quaternary carbon atoms by Ireland ester Claisen rearrangement: total synthesis of (±)-herbertenolide, (±)-herberteneacetal, (±)-herbertene-1,14-diol and (±)-herbertene-1,15-diol,” Tetrahedron Lette.,vol. 46, pp. 4879 , 2005.
B. Wu, J. Chen, M. Li, J. Zhang, and X. Wang, “Highly Enantioselective Synthesis of Spiro[cyclohexanone-oxindoles] and Spiro[cyclohexanone-pyrazolones] by Asymmetric Cascade [5+1] Double Michael Reactions,” Eur. J. Org. Chem., pp.1318–1327, 2012.
Ch. Marti and E.Carreira, “Total Synthesis of (-)-Spirotryprostatin B: Synthesis and Related Studies,” J.Am. Chem. Soc, vol. 127, pp. 11505-11515, 2005.
I. Ungureanu, Ph. Klotz, A. Schoenfelder and A. Mann,” 2-Phenyl-N-tosylazetidine as a formal 1,4 dipole precursor,” Chem. Commun., pp. 958-959, 2001.
J. Jayashankaran, R. D. R.S Manian, and R. Raghunathan, “A facile entry into a novel class of dispiroheterocycles through 1,3dipolar cycloaddition,” ARKIVOC., vol. 11, pp. 32-39, 2005.
J. Ma, and S.M. Hecht, “Javaniside, a novel DNA cleavage agent from Alangium javanicum having a unusual oxindole skeleton,” Chem. Commun., pp. 1190–1191, 2004.
K. Aggarwal, and K. Vij, “An efficient catalyst free synthesis of nitrogen containing spiro heterocycles via [5 + 1] double Michael addition reaction,” RSC Adv., vol. 4, pp. 13313, 2014.
K. Ding, Y. Lu, N.Z. Coleska, S. Qiu, and Y. Ding, “Structure-Based Design of Potent Non-Peptide MDMZ Inhibitors” J. Am. Chem. Soc., vol. 127, pp. 10130–10131, 2005.
L. K. Smith, and I. R. Baxendale, “Total syntheses of natural products containing spirocarbocycles,” Org. Biomol. Chem., vol. 13, pp. 9907, 2015.
M. G. Assy, E. K. Mohamed, and A. S. Mohamed, “Heterocyclization of barbituric acid: Synthesis of novel condensed pyrimidines Reda A. Haggam,” Inter. J. of Adv. Res., vol. 3, pp. 692-698, 2015.
M. Ghandi, A. Yari, S. Jamal, and A. Taheri, “Synthesis of novel spiropyrrolidine through 1,3-dipolar cycloaddition,” Tetrahedron Lett., vol. 50, pp. 4724-472, 2009.
M. S. Hussein, “Synthesis, Characterization and Antibacterial Evaluation of Some Substituted Pyrrolidines,” Chem. Sci. Intern. J. , vol 17(2), pp. 1-8, 2016.

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Published

2018-12-30

How to Cite

Hussein, M. S., Al-Hamdany, A. W. J., & Saeed, R. A. (2018). Synthesis and Spectral Characterization of Some New Substituted Bis-spirocyclohexanones Derived from Acetone. Science Journal of University of Zakho, 6(4), 155–159. https://doi.org/10.25271/sjuoz.2018.6.4.548

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Science Journal of University of Zakho