55084-87-2Relevant academic research and scientific papers
Application of N-Acylbenzotriazoles in the Synthesis of 5-Substituted 2-Ethoxy-1,3,4-oxadiazoles as Building Blocks toward 3,5-Disubstituted 1,3,4-Oxadiazol-2(3H)-ones
Wet-Osot, Sirawit,Phakhodee, Wong,Pattarawarapan, Mookda
, p. 9923 - 9929 (2017/09/23)
5-Substituted-2-ethoxy-1,3,4-oxadiazoles were conveniently prepared through a one-pot sequential N-acylation/dehydrative cyclization between ethyl carbazate and N-acylbenzotriazoles in the presence of Ph3P-I2 as a dehydrating agent. Subsequent treatment with a stoichiometric amount of alkyl halides (X = Cl, Br, I) enables a rapid access to a variety of 3,5-disubstituted 1,3,4-oxadiazol-2(3H)-ones in good to excellent yields.
Syntheses and thermal rearrangements of 2-phenyl-4-alkoxycarbonyl-1,3,4-oxadiazol-5(4H)-ones and related sulfur compounds
Golfier, M.,Guillerez, M. G.
, p. 71 - 80 (2007/10/02)
Syntheses of nine 2-phenyl-4-alkoxycarbonyl-1,3,4-oxadiazol-5(4H)-ones are described.On heating about 200 deg C, these compounds decarboxylate and give 2-phenyl-4-alkyl-1,3,4-oxadiazol-5(4H)-ones.Although many analogies suggest that the rearrangement proceeds through the cyclisation of a 1,5-dipole, arising from the decarboxylation of the heterocycle, no direct evidence for such a mechanism was obtained.On the contrary, the synthesis and the thermal rearrangement of four related sulfur compounds show that such a postulated intermediate cannot explain all the experimental results.
