4-苯甲酰-5-苯基氨基-2,3-二氢噻吩-2,3-二酮与n -亲核试剂反应合成有机配体

IF 1.1 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Heteroatom Chemistry Pub Date : 2020-07-08 DOI:10.1155/2020/5945796

H. Kabirifard, Pardis Hafez Taghva, Hossein Teimouri, Niloofar Koosheshi, Parastoo Javadpour, Hanieh Bagherinejad, S. Seyfi, Maryam Hossein Roodbari, Elaheh Golabian

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引用次数: 0

摘要

4-苯甲酰-5-苯基氨基-2,3-二氢噻吩-2,3-二酮(1)与氨基异芳基、拉莫三嗪、1,3-二氨基异芳基、氨苯酮、NH2R(羟胺、l- 1-苯乙胺、二甲双胍)和4,4 ' -联吡啶在室温THF/H2O(1:1)中反应得到3- n -苯基硫氨基-2-丁烯酰胺2-5。而以萘胺和1,3-苯二胺在乙醇中高温反应得到5-苯胺-2,5-二氢噻吩-2- 1 - 6-8为有机配体，产率较高。结果表明，除伯胺外，n -亲核试剂对噻吩-2,3-二酮环1的硫酯羧基(C-2)进行亲核攻击。然而，伯胺对噻吩-2,3-二酮1羰基(C-3)的亲核攻击以取代噻吩的形式发生。

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Synthesis of Organic Ligands via Reactions of 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione with N-Nucleophiles

The reaction of 4-benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione (1) with aminoheteroaryls, lamotrigine, 1,3-diaminoheteroaryls, dapsone, NH2R (hydroxylamine, DL-1-phenylethylamine, and metformin), and 4,4′-bipyridine in THF/H2O (1 : 1) at room temperature led to 3-N-phenylthiocarbamoyl-2-butenamides 2–5, while that with naphthylamines and 1,3-phenylenediamine in ethanol at high temperature led to 5-phenylamino-2,5-dihydrothiophene-2-ones 6–8 as organic ligands in the medium to good yields. These showed the nucleophilic attacks of N-nucleophiles, except primary aromatic amines, on thioester carboxyl group (C-2) of thiophene-2,3-dione ring 1. However, the nucleophilic attacks of primary aromatic amines on the carbonyl group (C-3) of thiophene-2,3-dione 1 occurred in the form of substituted thiophenes.

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来源期刊

Heteroatom Chemistry 化学-化学综合

CiteScore

1.20

自引率

0.00%

发文量

审稿时长

6 months

期刊介绍： Heteroatom Chemistry brings together a broad, interdisciplinary group of chemists who work with compounds containing main-group elements of groups 13 through 17 of the Periodic Table, and certain other related elements. The fundamental reactivity under investigation should, in all cases, be concentrated about the heteroatoms. It does not matter whether the compounds being studied are acyclic or cyclic; saturated or unsaturated; monomeric, polymeric or solid state in nature; inorganic, organic, or naturally occurring, so long as the heteroatom is playing an essential role. Computational, experimental, and combined studies are equally welcome. Subject areas include (but are by no means limited to): -Reactivity about heteroatoms for accessing new products or synthetic pathways -Unusual valency main-group element compounds and their properties -Highly strained (e.g. bridged) main-group element compounds and their properties -Photochemical or thermal cleavage of heteroatom bonds and the resulting reactivity -Uncommon and structurally interesting heteroatom-containing species (including those containing multiple bonds and catenation) -Stereochemistry of compounds due to the presence of heteroatoms -Neighboring group effects of heteroatoms on the properties of compounds -Main-group element compounds as analogues of transition metal compounds -Variations and new results from established and named reactions (including Wittig, Kabachnik–Fields, Pudovik, Arbuzov, Hirao, and Mitsunobu) -Catalysis and green syntheses enabled by heteroatoms and their chemistry -Applications of compounds where the heteroatom plays a critical role. In addition to original research articles on heteroatom chemistry, the journal welcomes focused review articles that examine the state of the art, identify emerging trends, and suggest future directions for developing fields.