SHORT COMMUNICATION

Ph₃P catalyzed synthesis of alkyl 2-(4-oxopyridin-1(4H)-yl)acrylates by nucleophilic addition to alkyl propiolates

Bita Mohtat^{I, *} ; Setareh Azimzadeh^I; Hoorieh Djahaniani^II; Leila Pirhadi^I

^IChemistry Department, Islamic Azad University, Karaj Branch, Karaj, Iran
^IIChemistry Department, Islamic Azad University, East Tehran Branch, Qiamdasht, Tehran, Iran

ABSTRACT

4-Hydroxypyridine undergoes a smooth reaction with alkyl propiolates in the presence of triphenylphosphine to produce α and β-substituted alkyl acrylate products. When the reaction was performed with 4-hydroxyquinoline only α-substituted alkyl acrylates were obtained.

Keywords: 4-hydroxypyridine, 4-hydroxyquinoline, alkyl acrylates, alkyl propiolates, triphenylphosphine

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References

1 L.D. Quin, A Guide to Organophosphorus Chemistry, Wiley-Inter-science, New York, 2000.         [ Links ]

2 R. Engel, Synthesis of Carbon-phosphorus Bonds, CRC Press, Boca Raton, 1998.         [ Links ]

3 D.E.C. Cobridge, Phosphorus: An Outline of Chemistry, Biochemistry and Uses, 5th edn., Elsevier, Amsterdam, 1995.         [ Links ]

4 I. Yavari and A. Ramazani, Synth. Commun., 1997, 27, 1449-1454.         [ Links ]

5 I. Yavari and H. Norouzi-Arasi, Phosphorus, Sulfur, and Silicon, 2002, 177, 87-92.         [ Links ]

6 I. Yavari, S. Souri, M. Sirouspour, H. Djahaniani and F. Nasiri, Synthesis, 2005, 1761-1764.         [ Links ]

7 I. Yavari and M. Bayat, Tetrahedron, 2003, 59, 2001-2005.         [ Links ]

8 R.M. Acheson and N.F. Elmore, Adv. Heterocycl. Chem., 1978, 23, 263-482.         [ Links ]

9 R.M. Acheson and J. Woollard, J. Chem. Soc. Perkin Trans. 1, 1975, 438-445.         [ Links ]

10 I. Yavari, A.R. Alborzi and B. Mohtat, J. Chem. Res. (S), 2007, 401-403.         [ Links ]

11 (a) I. Yavari, N. Hazeri, M.T. Maghsoodlou and S. Souri, J. Mol. Catalysis 2007, 264, 313 317.         [ Links ] (b) B. Mohtat, S. Jabbar, A. Ghasemi and I. Yavari, J. Chem. Res. (S), 2008, 601-603        [ Links ]

12 Y. Shen, Acc. Chem. Res., 1998, 31, 584-592.         [ Links ]

Received 7 October
Revised 9 November
Accepted 18 November 2010

* To whom correspondence should be addressed. E-mail: b.mohtat@jooyan.org