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Mononuclear heterocyclic rearrangements. Effect of the structure of the side chain on the reactivity. Part 3. Rearrangement of some N-(5-phenyl-1,2,4-oxadiazol-3-yl)-N′-arylformamidines into 1-aryl-3-benzoylamino-1,2,4-triazoles in acetonitrile in the presence of triethylamine

✍ Scribed by Vincenzo Frenna; Gabriella Macaluso; Nicolò Vivona; Domenico Spinelli; Giovanni Consiglio; Elisabetta Mezzina

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 754 KB
Volume: 50
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)85255-8

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✦ Synopsis

A~tract:~~~~~rats~~fartheti~enactiongiveacwilinearplotvrr~tertiaryamine concentration, according to the quatim kA = (& + Kt~LZ[TEAl)/(l + KtmA]). This shows the occure.nce of two different reaction pathways; the one, Wepndent of ml and the other, dependaN on ITEA]. which involves a fast convcxsion of the substrate into an acid-b &uct or aa ion pair followed by its slow conversion into the umqonding Iriazole.lllesubs~teffectsontbeaeructionshaverlsobee-nstudicd. In the framework of our synthetic2 and mechanistic1~3 studies on heterocyclic rearrangements we have recently exam&d the effect of the S~~KV,UR of the side chain on the xeactivity13~4 in mononuclear heterocyclic rearrangements (MHRs).~ For example, the rearrangements of some derivatives of 1.2,4-oxadiazde were studied in dioxane-water @10X-W) in a large range of p5? (Scheme l).l 'Ihe side chains considered were PhCONH b 1 Scheme

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