A simple and efficient approach for the synthesis of a novel class aliphatic 1,3,4-thiadiazol-2(3H)-one derivatives via intramolecular nucleophilic substitution reaction

Hakan Tahtaci; G?zde Ayd?n

首页> 外文期刊>Synthetic Communications >A simple and efficient approach for the synthesis of a novel class aliphatic 1,3,4-thiadiazol-2(3H)-one derivatives via intramolecular nucleophilic substitution reaction

【24h】

A simple and efficient approach for the synthesis of a novel class aliphatic 1,3,4-thiadiazol-2(3H)-one derivatives via intramolecular nucleophilic substitution reaction

机译：通过分子内亲核取代反应合成新类脂族1,3,4-噻唑-2（3H）衍生物的简单有效的方法

获取原文

获取原文并翻译 | 示例

掌桥外文数据库（机构版） >>

开具论文收录证明 >>

文献代查 >>

页面导航

摘要
著录项
相似文献
相关主题

摘要

In this study, we synthesized a new series of substituted aliphatic 1,3,4-thiadiazol-2(3H)-one derivatives (6-24) in yields ranging from 42 to 70% with an interesting mechanism that involves internal nucleophilic substitution followed by an S_N2-type nucleophilic substitution. First, 1-(4-chlorophenyl)-2-((5-methyl-1,3,4-thiadiazol-2-yl)thio)ethanone (3) was synthesized from the reaction of 5-methyl-1,3,4-thiadiazole- 2-thiol (1) with 2-bromo-1-(4-chlorophenyl)ethanone (2) in the presence of potassium hydroxide. Then, 1-(4-chlorophenyl)-2-((5- methyl-1,3,4-thiadiazol-2-yl)thio)ethanol (4) was synthesized by a reduction reaction of this compound using NaBH_4. Finally, 5-methyl- 3-alkyl-1,3,4-thiadiazol-2(3H)-one derivatives (6-24), which are the target compounds, were synthesized from the reaction of this compound (4), which is a secondary alcohol with various alkyl halides (5a-n) in the presence of sodium hydride (NaH). This study presents an interesting reaction mechanism related to the synthesis of aliphatic 1,3,4-thiadiazol-2(3H)-one derivatives that is not recorded in the literature.

机译：在这项研究中，我们合成了一系列新的取代脂族1,3,4-噻唑-2（3H） - 衍生物（3H）的产率，其产量为42-70％，其涉及内部亲核取代所涉及的有趣机制通过S_N2型亲核替代。首先，从5-甲基-1,3的反应合成1-（4-氯苯基）-2-（（5-甲基-1,3,4-噻唑-2-基二溴唑-2-基）硫酮（3），在氢氧化钾存在下，具有2-溴-1-（4-氯苯基）乙醇（2）的4-噻二唑-2-硫醇（1）。然后，通过使用NaBH_4的该化合物的还原反应合成1-（4-氯苯基）-2-（（5-甲基-1,3,4-噻二唑-2-基二元）硫醇（4）。最后，通过该化合物（4）的反应合成5-甲基-3-烷基-1,3,4-噻唑-2（3H） - 衍生物（6-24），其是目标化合物，其是氢化钠（NAH）存在下具有各种烷基卤化物（5A-N）的二次醇。本研究提出了一种有趣的反应机制，其与合成脂族1,3,4-噻唑-2（3H）-ONE衍生物，该衍生物未记录在文献中。

著录项

来源
《Synthetic Communications》 |2019年第20期|共12页
作者
Hakan Tahtaci; G?zde Ayd?n;
展开▼
作者单位

Department of Chemistry Faculty of Science Karabuk University Karabuk 78050 Turkey;

Department of Chemistry Faculty of Science Karabuk University Karabuk 78050 Turkey;

展开▼
收录信息
原文格式 PDF
正文语种 eng
中图分类有机化学;
关键词
Aliphatic 1; 3; 4-thiadiazol- 2(3H)-one; intramolecular nucleophilic substitution reaction; 1; 3; 4-thiadiazole derivatives;

机译：脂肪族1;3;4-噻唑-2（3H） - 酮;分子内亲核取代反应;1;3;4-噻二唑衍生物;

相似文献

外文文献
中文文献
专利

1. A simple and efficient approach for the synthesis of a novel class aliphatic 1,3,4-thiadiazol-2(3H)-one derivatives via intramolecular nucleophilic substitution reaction [J] . Hakan Tahtaci, G?zde Ayd?n Synthetic Communications . 2019,第17a20期

机译：通过分子内亲核取代反应合成新类脂族1,3,4-噻唑-2（3H）衍生物的简单有效的方法
2. Sulfamic acid-mediated, efficient, one-pot synthesis of novel 5-substituted 1,3,4-thiadiazol-2-ylcarbamoyl aliphatic amide acid derivatives and facile synthesis of cyclic amides [J] . Toche R.B., Janrao R.A., Gangurde S.A., Synthetic Communications . 2013,第16a18期

机译：氨基磺酸介导的一锅法合成新型5-取代的1,3,4-噻二唑-2-基氨基甲酰基脂族酰胺酸衍生物，并轻松合成环酰胺
3. A simple and efficient approach for the synthesis of new 1,3,4- oxadiazoles via a two-component reaction of N- isocyaniminotriphenylphosphorane and electron-rich benzoic acid derivatives [J] . Ali Ramazani, Ali Souldozi, Pegah Azimzadeh Asiabi Organic chemistry: an Indian journal . 2015,第12期

机译：一种简单有效的方法，可通过N-异氰基亚氨基三苯基膦与富电子的苯甲酸衍生物的两组分反应合成新的1,3,4-恶二唑
4. Michael Addition Reactions between Nucleophilic GlycineEquivalents and Acrylic Acid Derivatives as a Practicaland Generalized Approach to the Asymmetric Synthesisof II-Substituted-a-Amino Acids [C] . Vadim A. Soloshonok, Hisanori Ueki, Trevor K. Ellis ACS symposium asymmetric synthesis and application of α-amino acids . 2009

机译：亲核糖糖糖尿剂与丙烯酸衍生物之间的迈克尔添加反应作为不对称合成的不对称 - A-氨基酸的不对称方法的普遍化方法
5. I. Pyridoxal-apoenzyme mimics designed for transimination and selective racemization. II. Effects of organic cosolvents on nucleophilic aliphatic substitution (S(N)2) reactions in water [D] . Mayer, Miriam Uljana 1999

机译：一，设计用于转座和选择性消旋的吡rid醛-辅酶模拟物。二。有机助溶剂对水中亲核脂肪族取代（S（N）2）反应的影响
6. Efficient synthesis of 5-substituted 2-aryl-6-cyanoindolizines via nucleophilic substitution reactions [O] . Eugene V Babaev, Natalya I Vasilevich, Anna S Ivushkina 2005

机译：通过亲核取代反应高效合成5-取代的2-芳基-6-氰基吲哚嗪
7. Ugi Multicomponenet Reaction Followed by an Intramolecular Nucleophilic Substitution: Convergent Multicomponent Synthesis of 1-Sulfonyl 1, 4-Diazepan-5-ones and of Their Benzo-Fused Derivatives [O] . -1

机译：UGI多组分反应，接着是分子内的亲核代替：1-磺酰基1,4-二氮杂-5-和苯并融合衍生物的会聚多组分合成

A simple and efficient approach for the synthesis of a novel class aliphatic 1,3,4-thiadiazol-2(3H)-one derivatives via intramolecular nucleophilic substitution reaction

摘要

著录项

相似文献

相关主题

期刊订阅