Abstract
Consecutive treatment of the available 4-(dichloromethylene)-4-phenyl-1,3-oxazol-5(4H)-one with triphenylphosphine, water, and triethylamine gives a stabilized ylide Ph3P=CHCONHCOPh. Its structure was proved by X-ray diffraction. The ylide reacts with hydrogen chloride and phosphorus pentachloride to give a many-center phosphonium reagent with a 1,3-dichloro-2-aza-1,3-diene group, which enters cyclocondensations with hydrazine hydrate, phenylhydrazine, and benzamidine. These reactions allowed synthesis of phosphonium salts of the general formula Ph3 \(\mathop P\limits^ +\)CH2HtAn− derived from 1,2,4-triazole or 1,3,5-triazine. The structure of the cyclization products was established by spectral methods, as well as by alkaline dephosphorylation.
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Translated from Zhurnal Obshchei Khimii, Vol. 74, No. 9, 2004, pp. 1434–1440.
Original Russian Text Copyright © 2004 by Brovarets, Golovenko, Sviripa, Zyuz’, Chernega, Drach.
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Brovarets, V.S., Golovenko, A.V., Sviripa, V.N. et al. New transformations of the reaction product of 4-(dichloromethylene)-2-phenyl-1,3-oxazol-5(4H)-one with triphenylphosphine. Russ J Gen Chem 74, 1328–1334 (2004). https://doi.org/10.1007/s11176-005-0005-8
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DOI: https://doi.org/10.1007/s11176-005-0005-8