Synthesis of New Organophosphorus Compounds Derived from 2- Arylidenecyclohexane-1-one

Authors

  • Mona Hizkial Arsanious Department of Organometallic and Metalloid Chemistry, National Research Center Giza, Egypt http://orcid.org/0000-0002-9362-2399
  • Ibtisam Hennawy Department of Organometallic and Organometalloid Chemistry National Research Centre, 33 El- Bahouth Street Dokki, P.O. Box 12622, Giza

Abstract

2-(4-Arylidene)cyclohexane-1-one derivatives react with 2,4- bis (phenylthio) -1,3-dithia,2,4- diphosphetane-2,4-disulphide (JR)  to give a mixture of the  benzo-dithiadiphosphi-nine -2-sulphides and dithiadispirotetradecanes. The same reaction was carried out using Lawesson's reagent to yield the 4-methoxyphenylbenzo-dithiaphosphinine sulfides. A putative reaction mechanism involves an initial thiation of arylidenecyclohexane-1-one derivatives then Michael addition by sulfide anion of Lawesson's reagents followed by intramolecular cyclization and resulting in the formation of new heterocyclic compounds containing phosphorus moiety. Biological activities for some of the new compounds are also reported. 

Author Biography

Mona Hizkial Arsanious, Department of Organometallic and Metalloid Chemistry, National Research Center Giza, Egypt

Department of Organometallic and Metalloid Chemistry, National Research Center Giza, Egypt

References

- Z. Hsn, S. Vehora, H. Shinokubo, K. Oshima, J. Org. Chem., 2001, 66, 7854; b) S. kobayashi, K. Kakunoto, M. Sugiura, Org. Lett. 2002 , 4, 1319.

- F. Fulop, G. Bemath, K. Pihlaja, Adv. Heterocycl.Chem., 1998, 69, 349.

- J. Deli, T. Lorand, D. Szabo, A. Faldesi, Pharmazie 1984, 39, 539.

- M. N. Arsanious, N. K. El- Din, L. S. Boulos, Phos., Sul. and Sili. 2009, 184, 2813.

- S. Javanshir, M. M. Mojtahedi, J. Eshami, Curr. Chem. Lett. 2014, 3, 63.

- K Ranjith, L. Balaganesan,, P. Subbu., Synth. Comm. 2009, 39, 3197; b) N. Singh, J. Pandey, A. Yadav, V. Chaturvedi, S. Bhatnagar, A. N. Gaikwad, S. K. Sinba, A. Kumar, 243 P. K. Shukla, R. P. Tripathi, Eur. J. Med. Chem 2009, 44 , 1705.

- W. M. Weber, L. A. Hunsaker, S. F. Abcouwer, L. M. Deck, D. L. Vander Jagt, Bioorg. Med. Chem, 2005, 13, 3811; b) A. Modzelewska, C. Pettit, G. Achanta, E. Davidson , P. Huang, S. R. Khan, Bioorg Med Chem 2006, 14, 3491.

- T. P. Robinson, T. Ehlers, R. B. Hubbard, X. Bai , J. L. Arbiser, D. J. Goldsmith, J. P. 248 Bowena, Bioorg. Med. Chem. Lett. 2003, 13, 115.

- T. P. Robinson, R. B. Hubbard, T. Ehlers, J. L. Arbiser, D. J. Goldsmith, J. P. Bowena, Bioorg. Med. Chem. 2005,13,4007.

- J. R. Dimmock, M. P. Padmanilagan, G. A. Zello, K. H. Nienaber, T. M. Allen, L. Santos, E. De Clerck, J. Balzarini, E. K. Manavathu, J. P. Stables, Eur. J. Med. Chem 2003, 38 169.

- A. Modzelewska, C. Pettit, G. Achanta, N. E. Davison, P. Haung, S. R. Khan, Bioorg. Med., Chem. 2006, 14, 3491.

- C. Piantadosi, I. H. Hall, J. L. Irvin, G. L. Carlson, J. Med. Chem. 1973,16 , 770.

- M. Ogawa, Y. Ishii, T. Nakano, S.Irifune, Jpn Kohai Tokkya JP. 632192446 A2 1988 (C.A. 1988, 63, 238034).

- R. N. Dighore, P. L. Anandgaonker, S. T. Gaikwad, A. S. Rajbhoj, Mater. Sci. Pol., 33 2015, 259, 163.

- M. N. Arsanious, S. S. Maigali, L. S. Boulos, Phos., Sul. and Sili. 2010, 185, 57.

- a) C. M. Simpkins, D. A. Hunt, Tetra. Lett. 2013, 54, 3371;b) P. Perjesi, D. Szabo, G. Batta, A. Foldesi Tetra. Lett. 1987, 28 , 571.

- R. Shabana, S. S. Maigali, S. A. Essawy, S. A. El- Hussieny, M. F. Soliman, Egy. J. Chem. Special Issue (M.Sidky) 2007, 59.

- N. R. Mohamed, G. A. Elmegeed, H. A. Abd-El Malek , M. Younis, Stero. 2005, 70, 131.

- P. Venkateswarlu, S. Ch.Venkata, Tetra. Lett., 2004, 45 , 3207.

- D.H. William, I. Fleming In Spectroscopic Methods in Organic Chemistry, Mc Graw- Hill, Maidenhead, UK, 1987, p.55.

- M. Hesse, M. Meier, B. Zeeh, Spektroskopische Methoden in der Organischem Chemie Thieme Verlag, Stuttgart, Germany,1997, p 57.

- L. J. Bellamy, The Infrared Spectra of Complex Molecules, Wiley, New York, 1964, p 311.

- S. Scheibye, R. Shabana , S.O. Lawesson, Tetera. 1982, 38, 993.

- A. A El-Barbary, R. Shaban ,S. O. Lawesson, Phosphorus, Sulfur and Silicon 1985, 21, 375.

- B. Deschamps, J. Seyden-Penne, Tetra. 1977, 33, 413.

- L. S. Boulos, M. N. Arsanious, E. F. Ewies , Phosphorus, Sulfur and Silicon 2009, 184, 275.

- L. S. Boulos, M. N.Arsanious , E. F. Ewies, Ramzy F., Z. Natur. 2008, 63b, 1211.

- R.J. Grayer, B.J. Harborne, Phytochem. 1997, 37, 19.

- O.N. Irobi, M. Moo-Young, W. A. Anderson, Int.J. Pharmacog 1996, 34, 87.

- E. Jametz, J. L. Melnick, E. A. Aldelberg Review of Medical Microbiology, 5th ed., Lang Medical Publication: Los Altos, CA 1974, 57, 399.

- D. N. Muanza, B. W. Kim, K. L. Euler, L. Williams, Int. J. Pharmacog. 1994, 32, 337.

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Published

2016-05-14

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Organic Chemistry