15256-68-5Relevant academic research and scientific papers
Flash vacuum pyrolysis of 1,2,5-oxadiazole 2-oxides and 1,2,3-triazole 1-oxides
Mitchell, William R.,Paton, R. Michael
experimental part, p. 34 - 54 (2011/02/21)
The flash vacuum pyrolysis (FVP, 450-600 °C/10-3 mmHg) of 3,4-diaryl- and 3,4-dialkyl-1,2,5-oxadiazole 2-oxides (furoxans) has been investigated. In all cases the 1,2,5-oxadiazole ring cleaved cleanly at O(1)-N(2) and C(3)-C(4) to afford two nitrile oxide fragments, which were trapped in high yield (75-97%) as their isoxazoline cycloadducts by reaction with alk-1-enes. At higher temperatures (700-800 °C) isocyanates were formed as by-products. The dimerisation of acetonitrile oxide to dimethylfuroxan was followed by 1H NMR spectroscopy, and the rate constant for the 2 nd order reaction determined. The furoxans were converted into isocyanates in good yield (61-95%) by FVP, followed by sulfur dioxide-mediated isomerisation of the resulting nitrile oxides. 2,4,5-Trisubstituted-1,2,3- triazole 1-oxides showed greater thermal stability, but at 700-800 °C decomposition of the 4,5-dimethyl compound 25b lead to 1,2-di(5-methyl-2-phenyl- 1,2,3-triazol-2-yl)ethane as the major product; attempts to trap acetonitrile oxide were unsuccessful. ARKAT USA, Inc.
Extended Tandem Reactions of 2H-1,2,3-Triazole N-Oxides with Dialkyl Acetylenedicarboxylates and N-Phenylmaleimide: Substituted Monocyclic 2,5-Dihydro-1,2,3-triazines and New Tetrahydrofuro-1,2,3-triazoles. Azolium 1,3-Dipoles Part 5.
Butler, Richard N.,Cunningham, Desmond,Marren, Elizabeth G.,McArdle, Patrick
, p. 3321 - 3326 (2007/10/02)
The reaction of substituted 1,2,3-triazole 1-oxides with dialkyl acetylenedicarboxylate dipolarophiles gave a new route to monocyclic 1,2,3-triazine derivatives via a multi-step sequence of cycloaddition, sigmatropic rearrangements, and ring expansion.Wit
SYNTHESIS OF HETEROCYCLES: PART I. N-IODOSUCCINIMIDE, A CONVENIENT OXITATIVE CYCLISING AGENT IN THE SYNTHESIS OF OXAZOLE, ISOXAZOLE, BENZOFURAN, FUROXAN AND 1,2,3-TRIAZOLE-1-OXIDE DERIVATIVES
Talapatra, Sunil K.,Chaudhuri, Prabir,Talapatra, Bani
, p. 1279 - 1282 (2007/10/02)
N-Iodosuccinimide has been successfully employed as an oxidative cyclising agent for the synthesis of oxazole, isoxazole, benzofuran, furoxan and 1,2,3-triazole-1-oxide derivatives.Synthesis of compounds (II), (IV), (VI), (VIII) and (X) having these basic skeletons respectively are reported.
