OXIDATION AND REARRANGEMENT OF 5-SUBSTITUTED 5-ETHOXYCARBONYL[1,2,4]TRIAZOLIDINE-3-THIONES

Schantl Joachim; Lang Sergius

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OXIDATION AND REARRANGEMENT OF 5-SUBSTITUTED 5-ETHOXYCARBONYL[1,2,4]TRIAZOLIDINE-3-THIONES

机译：5-取代的5-乙氧基羰基[1,2,4]三唑啉-3-硫酮的氧化和重排

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The reaction of ethyl 2-(phenylhydrazono)alkanoates (1) with potassium thiocyanate in acetic acid affords 5-ethoxycarbonyl-substituted [1,2,4]triazolidine-3-thiones (3).Oxidation (KMnO_4) converts 3 into 1-ethoxy-carbonyl-2,3-dihydro-1H-[1,2,4]triazole-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.

机译：2-（苯基肼基）链烷酸乙酯（1）与硫氰酸钾在乙酸中的反应得到5-乙氧基羰基取代的[1,2,4]三唑烷-3-硫酮（3）。氧化（KMnO_4）将3转化为1-通过9a的X射线结构分析证明，乙氧基羰基-2,3-二氢-1H- [1,2,4]三唑-3-硫酮（9）。产物（9）由3的氧化转化产生到中间体（5）和环状价异构体（7），然后选择性地涉及5-乙氧基羰基迁移的[1,5] sigma-tropic重排。

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《Heterocycles: An International Journal for Reviews and Communications in Heterocyclic Chemistry》 |1999年第1期|共8页
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Schantl Joachim; Lang Sergius;
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1. OXIDATION AND REARRANGEMENT OF 5-SUBSTITUTED 5-ETHOXYCARBONYL[1,2,4]TRIAZOLIDINE-3-THIONES [J] . Schantl Joachim, Lang Sergius Heterocycles: An International Journal for Reviews and Communications in Heterocyclic Chemistry . 1999,第1期

机译：5-取代的5-乙氧基羰基[1,2,4]三唑啉-3-硫酮的氧化和重排
2. Construction of 3,5-substituted 1,2,4-oxadiazole rings triggered by tetrabutylammonium hydroxide: a highly efficient and fluoride-free ring closure reaction of O-acylamidoximes [J] . Hiromichi Otaka, Junya Ikeda, Daisuke Tanaka Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2014,第5期

机译：氢氧化四丁铵引发的3,5-取代的1,2,4-恶二唑环的构建：O-酰基酰胺基肟的高效无氟闭环反应
3. Tandem oxidation processes for the regioselective preparation of 5-substituted and 6-substituted 1,2,4-triazines [J] . Laphookhieo S, Jones S, Raw SA, Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2006,第23期

机译：串联氧化过程用于区域选择性制备5-取代和6-取代的1,2,4-三嗪
4. Synthesis and characterization of 5-substituted 1,2,4-triazole-3-methyl nitrate as potential high-performance energetic plasticizers [C] . Rui Yang, Zhiwen Ye Seminar on new trends in research of energetic materials . 2020

机译：5-取代的1,2,4-三唑-3-甲基硝酸酯作为潜在的高性能含能增塑剂的合成与表征
5. I. PREPARATION AND PROPERTIES OF ALKYL AND ARYL SUBSTITUTED THIOQUINAZOLINES AND SULFOXIDES. II. AN INVESTIGATION OF THE QUINAZOLINE 3-OXIDE-1,4-BENZODIAZEPINE 4-OXIDE REARRANGEMENT. [D] . KUCHAR, MARVIN C. J. 1964

机译：I.烷基和芳基取代的噻喹唑啉和磺胺氧化物的制备和性质。二。喹唑啉3-氧化物-1,4-苯并二氮杂4-氧化物重排的研究。
6. Boulton-Katritzky Rearrangement of 5-Substituted Phenyl-3-2-(morpholin-1-yl)ethyl-124-oxadiazoles as a Synthetic Path to Spiropyrazoline Benzoates and Chloride with Antitubercular Properties [O] . Lyudmila Kayukova, Anna Vologzhanina, Kaldybai Praliyev, 2021

机译：Boulton-Katritzky的5-取代的苯基-3- 2-（吗啉-1-基）乙基 -124-二唑作为螺丝唑啉苯甲酸盐和氯化物的合成途径具有抗胆管性能
7. Studies on as-triazine derivatives. IX Synthesis of 5-substituted 1,2,4-triazine derivatives through an addition reaction and subsequent oxidation. [O] . SHOETSU KONNO, SETSUYA OHBA, MATAICHI SAGI, 1987

机译：基于三嗪衍生物的研究。 IX通过添加反应和随后的氧化合成5取代的1,2,4-三嗪衍生物。
8. 3-Amino-1,2,4-Benzotriazines and Their N-Oxides as Antifolate-Antimalarials. [R] . Parish, W. W., Johnston, W. D. 1976

机译：3-氨基-1,2,4-苯并三嗪及其N-氧化物作为抗叶酸 - 抗疟药。

OXIDATION AND REARRANGEMENT OF 5-SUBSTITUTED 5-ETHOXYCARBONYL[1,2,4]TRIAZOLIDINE-3-THIONES

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