Temperature-controlled S vs N selective alkylation of 1-phenyl tetrazole-5-thione with α,β-unsaturated systems in solvent-free organic salt media

IF 2.1 3区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Sulfur Chemistry Pub Date : 2023-02-02 DOI:10.1080/17415993.2023.2173010
Siamak Atabak , Gholamhassan Imanzadeh , Roghayyeh Asgharzadeh , Zahra Soltanzadeh , Turan Öztürk
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Abstract

In this work, a novel series of N and S-alkylated derivatives of 1-phenyl tetrazole-5-thione were synthesized by Michael addition in organic salt media TBAB (Tetrabutylammonium bromide) using inorganic base K2CO3 under solvent-free conditions. The new and conveniently synthesized products showed unusual regioselectivity during the reaction. S-Michael adducts via reaction between 1-phenyl tetrazole-5-thione and acrylic esters as well as acrylonitrile were afforded at room temperature and N-Michael adducts obtained at 70°C. Both reactions occurred within 24 h. Surprisingly, using fumarate esters as Michael acceptor proceeded a SN2 reaction at 100°C due to steric effects. The structures of products all were confirmed by 1H and 13C NMR spectra and target compound yields were good to excellent.

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在无溶剂有机盐介质中1-苯基四唑-5-硫酮与α,β-不饱和体系的S vs N选择性烷基化反应
在无溶剂条件下,以无机碱K2CO3为原料,在TBAB(四丁基溴化铵)有机盐介质中采用Michael加成法合成了一系列新的N和s烷基化的1-苯基四唑-5-硫酮衍生物。新合成产物在反应过程中表现出不同寻常的区域选择性。1-苯基四唑-5-硫酮与丙烯酸酯和丙烯腈在室温下反应得到S-Michael加合物,在70℃下反应得到N-Michael加合物。两种反应均在24h内发生。令人惊讶的是,使用富马酸酯作为Michael受体,由于空间位阻效应,在100°C下发生SN2反应。产物的结构经1H和13C核磁共振谱证实,目标化合物产率均在良好至优异之间。图形抽象
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来源期刊
Journal of Sulfur Chemistry
Journal of Sulfur Chemistry CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
4.10
自引率
9.10%
发文量
38
审稿时长
6-12 weeks
期刊介绍: The Journal of Sulfur Chemistry is an international journal for the dissemination of scientific results in the rapidly expanding realm of sulfur chemistry. The journal publishes high quality reviews, full papers and communications in the following areas: organic and inorganic chemistry, industrial chemistry, materials and polymer chemistry, biological chemistry and interdisciplinary studies directly related to sulfur science. Papers outlining theoretical, physical, mechanistic or synthetic studies pertaining to sulfur chemistry are welcome. Hence the target audience is made up of academic and industrial chemists with peripheral or focused interests in sulfur chemistry. Manuscripts that truly define the aims of the journal include, but are not limited to, those that offer: a) innovative use of sulfur reagents; b) new synthetic approaches to sulfur-containing biomolecules, materials or organic and organometallic compounds; c) theoretical and physical studies that facilitate the understanding of sulfur structure, bonding or reactivity; d) catalytic, selective, synthetically useful or noteworthy transformations of sulfur containing molecules; e) industrial applications of sulfur chemistry; f) unique sulfur atom or molecule involvement in interfacial phenomena; g) descriptions of solid phase or combinatorial methods involving sulfur containing substrates. Submissions pertaining to related atoms such as selenium and tellurium are also welcome. Articles offering routine heterocycle formation through established reactions of sulfur containing substrates are outside the scope of the journal.
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