OXIDATION AND REARRANGEMENT OF 5-SUBSTITUTED 5-ETHOXYCARBONYL1,2,4TRIAZOLIDINE-3-THIONES

Schantl Joachim; Lang Sergius

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OXIDATION AND REARRANGEMENT OF 5-SUBSTITUTED 5-ETHOXYCARBONYL1,2,4TRIAZOLIDINE-3-THIONES

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The reaction of ethyl 2-(phenylhydrazono)alkanoates (1) with potassium thiocyanate in acetic acid affords 5-ethoxycarbonyl-substituted 1,2,4triazolidine-3-thiones (3).Oxidation (KMnO_4) converts 3 into 1-ethoxy-carbonyl-2,3-dihydro-1H-1,2,4triazole-3-thiones (9)as evienced by the X-Ray structure analysis of 9a .Products (9) result from an oxidative conversion of 3 to the intermediated (5) and the cyclic valence isomers (7) followed by 1,5 sigma-tropic rearrangement selectively involving the 5-ethoxycarbonyl group to migrate.

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《Heterocycles: An International Journal for Reviews and Communications in Heterocyclic Chemistry 》 |1999年第1期| 251-258| 共8页
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Schantl Joachim; Lang Sergius;
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2. ChemInform Abstract: Oxidation and Rearrangement of 5‐Substituted 5‐Ethoxycarbonyl1,2,4triazolidine‐3‐thiones. [J] . Joachim G. Schantl, Sergius Lang, Klaus Wurst Chem Inform . 1999 ,第23期

机译：ChemInform Abstract: Oxidation and Rearrangement of 5‐Substituted 5‐Ethoxycarbonyl1,2,4triazolidine‐3‐thiones.
3. ChemInform Abstract: 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 [J] . V. FRENNA, G. MACALUSO, N. VIVONAD. SPINELLIG. CONSIGLIOE. MEZZINA Chem Inform . 1994 ,第46期

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8. Theoretical Prediction of the Heat of Formation, Density, and Relative Sensitivity for 3,7-dinitro-[1,2,4]triazolo[5,1-c][1,2,4] triazin-4-amine. [R] . Byrd, E. F. 2015

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OXIDATION AND REARRANGEMENT OF 5-SUBSTITUTED 5-ETHOXYCARBONYL1,2,4TRIAZOLIDINE-3-THIONES

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