Abstract
The adducts produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates were trapped by arylsulfonyl isocyanates to produce dialkyl 2,5-dihydro-5-oxo-1,2-azaphosphole-3,4-dicarboxylates in good yields.
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References
Hudson, H.R., The Chemistry of Organophosphorus Compounds: Primary, Secondary, and Tertiary Phosphines and Heterocyclic Organophosphorus (III) Compounds, Vol. 1, Wiley, 1990, pp. 386–472.
Engel, R., Synthesis of Carbon–Phosphorus Bonds, CRC Press, Boca Raton, FL, 1988.
Cadogan, J.I.G., Organophosphorus Reagentsi in Organic Synthesis, Academic Press, New York, 1979.
Cherkasov R.A. and Pudovik, M.A., Heterophosphacyclanes in organic synthesis, Russ. Chem. Rev., 63 (1994) 1019–1045.
Yavari, I., Alizadeh, A. and Anary-Abbasinejad, M., Efficient synthesis of functionalized 2,5-Dihydro-1,2-oxaphospholes, Tetrahedron Lett., 44 (2003) 2877–2879.
Yavari, I. and Alizadeh, A., The formation of beta-lactam derivatives through the reaction of dibenzoylacetylene and aryl isocyanates in the presence of trivalent phosphorous nucleophiles, Synthesis (2004) 237–240.
Maryanoff, B.E. and Reitz, A.B., The wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. stereochemistry, mechanism, and selected synthetic aspects, Chem. Rev., 89 (1989) 863–927.
Yavari, I. and Alizadeh, A., reaction between triphenylphosphine and arylsulfonylglycyl chlorides. synthesis of N-[(Z)-2-(1-Hydroxy-1,1,1-triphenylphosphoranyl)ethenyl]-1-Arylsulfonamides, Tetrahedron, 57 (2001) 9873–9875.
Silverstein, R.M., Bassler, G.C. and Morrill, T.C., Spectroscopic Identification of Organic Compounds, 5th Edn., Wiley, New York, pp. 118–120.
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Yavari, I., Alizadeh, A. & Anary-Abbasinejad, M. Synthesis of dialkyl 2,5-dihydro-5-oxo-1,2-azaphosphole-3,4-dicarboxylates. Mol Divers 9, 241–244 (2005). https://doi.org/10.1007/s11030-005-3051-6
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DOI: https://doi.org/10.1007/s11030-005-3051-6