Synthesis of Dialkyl 2-(4-oxopyridin-1(4H)-yl)dicarboxylates Through the Reaction of 4-hydroxypyridine and Dialkyl Acetylenedicarboxylate in the Presence of Triphenylphosphine
DOI:
https://doi.org/10.29356/jmcs.v55i3.827Keywords:
4-Hydroxypyridine, dialkyl acetylenedicarboxylates, triphenylphosphine, dialkyl 2-(4-oxopyridin-1(4H)-yl)but-2-enedioates.Abstract
4-Hydroxypyridine undergoes a smooth reaction with dialkylacetylenedicarboxylates in the presence of triphenylphosphine (15
mol %) to produce the E/Z isomers of dialkyl 2-(4-oxopyridin-1(4H)-yl)but-2-enedioates in high yields.
Downloads
References
Winterfeldt, E. Angew. Chem. Int. Ed. Engl. 1967, 6, 423-434.
Butterfield, P. J.; Tebby, J. C.; Griffiths, D. V. J. Chem. Soc., Perkin Trans. 1979, 1, 1189-1191.
Acheson, R. M.; Plunkett, A. O. J. Chem. Soc. 1964, 2676-2683.
Winterfeldt, E.; Dillinger, H. J. Chem. Ber. 1966, 99, 1558-1568.
Winterfeldt, E.; Schumann, D.; Dillinger, H. J. Chem. Ber. 1969, 102, 1656-1664.
Yavari, I.; Ramazani, A. Synth. Commun. 1997, 27, 1449-1454.
Bayat, M.; Imanieh, H.; Hassanzadeh, F. Tetrahedron Lett. 2010, 51, 1873-1875.
Yavari, I.; Souri, S.; Sirouspour, M.; Djahaniani, H.; Nasiri, F. Synthesis, 2005, 1761-1764.
Yavari, I.; Bayat, M. Tetrahedron, 2003, 59, 2001-2005.
Acheson, R. M.; Elmore, N. F. Adv. Heterocycl. Chem. 1978, 23, 263-285.
Acheson, R. M.; Woolard, J. J. Chem. Soc. Perkin Trans. 1975, 1, 438-446.
Yavari, I.; Alborzi, A. R.; Mohtat, B. J. Chem. Res. (S) 2007, 152-154.
Mohtat, B.; Jabbar, S.; Ghasemi, A.; Yavari, I. J. Chem. Res. (S) 2008, 601-603.
Mohtat, B.; Azimzadeh, S.; Djahaniani, H.; Pirhadi, L. S. Afr. J. Chem. 2010, 63, 204-206.
Yavari, I.; Alborzi, A. R.; Mohtat, B.; Nourmohammadian, F. Synth. Commun. 2008, 38, 703-712.
Eliel, E. L.; Wilen, S. H. Stereochemistry of organic compounds, John Wiley & Sons, Inc, New York, 1994, pp. 569 -70.
Shen, Y. Acc. Chem. Res. 1998, 31, 584-592.
Downloads
Published
Issue
Section
License
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.