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Paper | Regular issue | Vol 68, No. 11, 2006, pp.2269-2283
Published online, 22nd September, 2006
DOI: 10.3987/COM-06-10842
Synthesis of Novel 1,3,4-Oxadiazin-5(6H)-ones and 2-Hydroxymethyl-1,3,4-oxadiazoles

Agnieszka Kudelko* and Wojciech Zielinski

*Department of Organic Technology and Petrochemistry, Silesian University of
Technology, Ul. Krzywoustego 4, PL-44101 Gliwice, Poland


Reactions of α-hydroxyacid hydrazides (benzilic, R- and S-mandelic) and triethyl orthoesters (orthoformate, orthoacetate, orthopropionate, orthobenzoate) in glacial acetic acid resulted in two groups of heterocyclic compounds, derivatives of 6-phenyl-1,3,4-oxadiazin-5-(6H)-one and 2 hydroxymethyl-1,3,4-oxadiazole. Their structures were confirmed by typical spectroscopic methods and X-Ray analysis. Spectral characteristic of the compounds and attempts to elucidate the mechanism are discussed.