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Reaction Between Trimethyl phosphite, Dimethyl Acetylenedicarboxylate and 1,3-Dicarbonyl Compounds: An Efficient Method for the Synthesis of Dimethoxyphosphoryl Succinic Acid Dimethoxy Ester Derivatives
Corresponding Author(s) : Ali Asadipour
Asian Journal of Chemistry,
Vol. 25 No. 8 (2013): Vol 25 Issue 8
Abstract
The addition of a phosphorus nucleophile to an acceptor such as alkyne, certainly represents one of the most versatile and powerful tools for the formation of P-C bonds. This offers the possibility to access many diversely functionalized products. In this article, the reaction between trimethyl phosphite and dimethyl acetylenedicarboxylate (DMAD) with 1,3-dicarbonyl compounds such as dimedone, acetyl acetone and diethyl malonate proceeds smoothly to produce stable dimethoxyphosphoryl succinic acid dimethyl ester derivatives (4), (11) and (12) in excellent yields.
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- F. Palacios, C. Alonso and J.M. de los Santos, Chem. Rev., 105, 899 (2005) and the references cited therein.
- R. Engel and J.I. Cohen, Synthesis of Carbon-Phosphorus Bonds, Ch. 1, CRC Press, New York, vol. 1 (2004).
- R.R. Holmes, Acc. Chem. Res., 37, 746 (2004).
- B.E. Maryanoff and A.B. Reitz, Chem. Rev., 89, 863 (1989).
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- A.J. Arduago and C.A. Stewart, Chem. Rev., 94, 1215 (1994).
- K.M. Pietrusiewiz and M. Zabloka, Chem. Rev., 94, 1375 (1994).
- H.J. Bestmann and O. Vostrowsky, Top. Curr. Chem., 109, 85 (1983).
- M. George, V.S.K. Khetan and P.K. Gupta, Adv. Heterocycl. Chem., 19, 354 (1976).
- R. Burgada, Y. Leroux, M. Zabloka and Y.U. Elkhoshnieh, Tetrahedron Lett., 22, 3533 (1981).
- H.R. Hudson, The Chemistry of Organophosphorus Compounds, Wiley, New York, vol. 1, p. 386 (1990).
- I. Yavari, Z. Hossaini and E. Karimi, Monatsh. Chem., 138, 1267 (2007).
- I. Yavari, Z. Hossaini and A. Alizadeh, Monatsh. Chem., 137, 1083 (2006).
References
F. Palacios, C. Alonso and J.M. de los Santos, Chem. Rev., 105, 899 (2005) and the references cited therein.
R. Engel and J.I. Cohen, Synthesis of Carbon-Phosphorus Bonds, Ch. 1, CRC Press, New York, vol. 1 (2004).
R.R. Holmes, Acc. Chem. Res., 37, 746 (2004).
B.E. Maryanoff and A.B. Reitz, Chem. Rev., 89, 863 (1989).
(a) I. Yavari and M.H. Mosslemin, Tetrahedron, 54, 9169 (1998); (b) I. Yavari, M.H. Mosslemin and A.R. Montahaei, J. Chem. Res., (S) 576 (1998); (c) I. Yavari, M. Adib and L. Hojabri, Tetrahedron, 57, 7537 (2001); (d) I. Yavari and M. Adib, Tetrahedron, 57, 5873 (2001); (e) I. Yavari and A. Alizadeh, Tetrahedron, 57, 9873 (2001); (f) I. Yavari, M. Adib and M.H. Sayahi, Tetrahedron Lett., 43, 2927 (2002); (g) I. Yavari, M. Adib and M.H. Sayahi, J. Chem. Soc., Perkin Trans. I, 1517 (2002); (h) I. Yavari, M. Anari-Abbasinejad and Z. Hossaini, Org. Biomol. Chem., 1, 560 (2003); (i) I. Yavari and N. Zabarjad-Shiraz, Monatsh Chem., 134, 445 (2003); (j) I. Yavari, M. Adib, Sh. Abdolmohammadi and M. Aghazadeh, Monatsh. Chem., 134, 1093 (2003); (k) I. Yavari and M. Bayat, Monatsh. Chem., 134, 1221 (2003); (l) I. Yavari and A. Alizadeh, Synthesis, 237 (2004); (m) M.H. Mosslemin, I. Yavari, M. Anary-Abbasinejad and M.R. Nateghi, Synthesis, 1029 (2004); (n) I. Yavari and A. Alizadeh, Mendeleev Commun., 15, 154 (2005).
A.J. Arduago and C.A. Stewart, Chem. Rev., 94, 1215 (1994).
K.M. Pietrusiewiz and M. Zabloka, Chem. Rev., 94, 1375 (1994).
H.J. Bestmann and O. Vostrowsky, Top. Curr. Chem., 109, 85 (1983).
M. George, V.S.K. Khetan and P.K. Gupta, Adv. Heterocycl. Chem., 19, 354 (1976).
R. Burgada, Y. Leroux, M. Zabloka and Y.U. Elkhoshnieh, Tetrahedron Lett., 22, 3533 (1981).
H.R. Hudson, The Chemistry of Organophosphorus Compounds, Wiley, New York, vol. 1, p. 386 (1990).
I. Yavari, Z. Hossaini and E. Karimi, Monatsh. Chem., 138, 1267 (2007).
I. Yavari, Z. Hossaini and A. Alizadeh, Monatsh. Chem., 137, 1083 (2006).