- Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions
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Aerobic visible-light induced intermolecular S?N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4-thiadiazoles can be obtained from thioamides. Preliminary mechanistic investigation suggested that the excited state of thioamides undergoes a single-electron-transfer (SET) process to afford thioamidyl radicals, which can be further transformed into a 1,2,4-thiadiazole through desulfurization and oxidative cyclization. The reaction has good functional group tolerance and represents a green method for the construction of S?N bonds.
- Wang, Hui,Xie, Shihua,Zhu, Hongjun,Zhuo, Liang
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supporting information
p. 3398 - 3402
(2021/06/25)
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- Multicomponent synthesis of diphenyl-1,3-thiazole-barbituric acid hybrids and their fluorescence property studies
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A series of novel diphenyl-1,3-thiazole linked barbituric acid hybrids (4) were prepared by two catalyst-free methods from readily available starting materials. The reaction of arylglyoxal, barbituric acid and aryl thioamides in the presence of 3-4 drops of water and liquid assisted grinding (LAG) provides the corresponding trisubstituted thiazoles tethered with a barbituric acid moiety within 30 minutes. Alternatively, a sequential two-step one-pot process involving aryl nitriles, ammonium sulphide, arylglyoxal and barbituric acid in water medium was developed. In this second method, in situ thioamides were prepared at room temperature from the reaction of alkyl/aryl nitriles and ammonium sulphide in aqueous medium. Arylglyoxal and barbituric acid were added to the in situ thioamides after neutralizing the reaction medium to provide trisubstituted thiazoles linked with barbituric acid derivatives. Some of our synthesized molecules showed fluorescent properties with very good quantum yields in DMSO medium. We also observed that fluorescent quantum yields of these thiazole derivatives depend on the type of electron donating/withdrawing character of R1 and R3. R2 has a very small effect on tuning the fluorescent properties. The salient features of this work are catalyst-free reactions, wide substrate scope, green reaction conditions (liquid assisted grinding and room temperature reactions in water medium) as well as the presence of more than one pharmaceutically important heterocyclic moiety with fluorescent properties.
- Mahata, Alok,Bhaumick, Prabhas,Panday, Anoop Kumar,Yadav, Rahul,Parvin, Tasneem,Choudhury, Lokman H.
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p. 4798 - 4811
(2020/04/03)
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- Method for synthesizing thiobenzamide derivative through CO2 regulation and control of substituted benzonitrile
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The invention discloses a method for synthesizing a thiobenzamide derivative through CO2 regulation and control of substituted benzonitrile. The method comprises the following steps: taking the substituted benzonitrile as a raw material, an inorganic sulfide as a sulfur source and CO2 as an auxiliary agent for reacting in the presence of a reaction solvent, and concentrating and purifying a reaction solution to obtain the thiobenzamide derivative. The reaction system disclosed by the invention is relatively simple, other catalysts are not added outside a reactant and the inorganic sulfide, themethod is suitable for synthesis of high-additional-value thiobenzamide containing a plurality of substituent groups, the reaction is carried out at low temperature and low pressure, and the risk coefficient is reduced.
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Paragraph 0037; 0038; 0040; 0041; 0042; 0049; 0050
(2019/01/24)
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- Arylacetamide compounds containing isothiazole ring and application of compounds
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The invention belongs to the field of fungicides, and relates to arylacetamide compounds containing an isothiazole ring and a fungicidal application of the compounds. The arylacetamide compounds containing the isothiazole ring are represented by a general
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Paragraph 0106-0109
(2019/07/11)
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- A 2, 4 - dimethyl thiazole-based acrylonitrile compounds and use thereof (by machine translation)
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The invention discloses a novel structure of the 2, 4 - dimethyl thiazole-based acrylonitrile compound or a stereoisomer thereof, a compound structure such as shown in formula I: In the formula: C R is selected from1 - C6 Alkyl, C1 - C6 Haloalkyl, C3 - C8 Cycloalkyl or C1 - C6 Alkoxy; Q is selected from the following group: R1 Is selected from H, halogen, methyl or trifluoromethyl; R2 Is selected from halogen; R3 , R4 Are independently selected from H, halogen, methyl or trifluoromethyl; or a stereoisomer thereof. The formula I compounds have excellent insecticidal, acaricidal activity, can be used for the pest, mites. (by machine translation)
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Paragraph 0100; 0101; 0102; 0103
(2017/08/02)
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- A 2, 4 - dimethyl [...] acrylonitrile compounds and use thereof
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The invention discloses a 2,4-dimethylthiazole acrylonitrile compound or a stereoisomer thereof with a novel structure. The structure of the compound is shown in the general formal (I) in the specification, wherein R is selected from alkyl of C1-C6, halogenated alkyl of C1-C6, naphthene of C3-C8 or alkoxy of C1-C6; Q is selected from the group as shown in the specification; R1 is selected from H, halogen, methyl or trifluoromethyl; R2 is selected from H, halogen, methyl or trifluoromethyl; or the stereoisomer of the compound is selected. The compound in the general formula I has excellent insect and mite killing activity, and can be used for preventing and controlling insects and mites.
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Paragraph 0102; 0103; 0104
(2017/12/27)
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- Synthesis, crystal structure, anti-HIV, and antiproliferative activity of new oxadiazole and thiazole analogs
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A series of 2-adamantyl-5-arylthiazolyl-1,3,4-oxadiazoles 7a–x together with thiazoles 13 and 14 were synthesized. Compounds 7a–l, 13, and 14 were tested in vitro with the aim of identifying novel lead compounds active against human immunodeficiency virus type-1 and human immunodeficiency virus type-2 activity in MT-4 cells. Title compounds were also tested against representatives of Gram-positive and Gram-negative bacteria (Staphylococcus aureus, Salmonella spp.), various mycobacterial strains (Mycobacterium fortuitum and Mycobacterium smegmatis), yeast (Candida albicans), and mold (Aspergillus fumigatus). None of the compounds showed antiviral or antimicrobial activity, except compounds 13 and 14 exhibited anti-human immunodeficiency virus-1 activity with EC50 values of 1.79 and 2.39 μM with Selectivity index = 18 and 4, respectively. On the other hand, compounds 7a and 7j showed a marked cytotoxicity against the human CD4+ lymphocytes (MT-4). Therefore, 7a and 7j were evaluated for their antiproliferative activity against two solid tumor-derived cell lines, which exhibited IC50 values of 8.1 ± 0.10 μM and 4.8 ± 0.08 μM against Hep-G2 cell lines, respectively.
- Khan, Mahmood-ul-Hassan,Hameed, Shahid,Akhtar, Tashfeen,Al-Masoudi, Najim A.,Al-Masoudi, Wasfi A.,Jones, Peter G.,Pannecouque, Christophe
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p. 2399 - 2409
(2016/10/25)
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- The BF3·OEt2-assisted conversion of nitriles into thioamides with Lawesson's reagent
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A method for the thiolysis of nitriles by applying Lawesson's reagent and facilitated by the addition of boron trifluoride-diethyl ether complex is reported. The method opens an easy access to primary thioamides. Aromatic, benzylic, and aliphatic nitriles were converted into the corresponding thioamides in high to quantitative yields (even in unfavorable cases, e.g., ortho-substitut-ed benzonitriles). The reaction was performed in 1,2-dimethoxyethane-tetrahydrofuran or toluene-diethyl ether solvent mixtures at 20-50°C, and exhibited considerable selectivity in the case of multifunctional nitrile substrates, such as cyanomethyl N-acetylphenylalaninate, benzoylacetonitrile, 4-cyanobenzamide, 4-acetylbenzonitrile, or pent-3-enenitrile. Georg Thieme Verlag Stuttgart.
- Nagl, Michael,Panuschka, Claudia,Barta, Andrea,Schmid, Walther
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experimental part
p. 4012 - 4018
(2009/05/27)
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- TiCl3OTf-[bmim]Br: a novel and efficient catalyst system for chemoselective one-pot synthesis of thioamides from arylaldoximes
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The combination of TiCl3OTf with 1-butyl-3-methylimidazolium bromide is found to be an efficient and novel catalytic system for chemoselective one-pot transformation of arylaldoximes to their corresponding thioamides in high to excellent yields.
- Noei, Jalil,Khosropour, Ahmad R.
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scheme or table
p. 6969 - 6971
(2009/04/07)
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- ARYLSULFONYL BENZYL ETHERS AS 5-HT2A ANTAGONISTS
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Compounds of formula (I) are potent and selective antagonists of the 5-HT2A receptor, and hence are useful in treatment of various CNS disorders.
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Page/Page column 20
(2010/11/23)
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- Benzo-fused lactams promote release of growth hormone
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There are disclosed certain novel compounds identified as benzo-fused lactams which promote the release of growth hormone in humans and animals. This property can be utilized to promote the growth of food animals to render the production of edible meat products more efficient, and in humans, to increase the stature of those afflicted with a lack of a normal secretion of natural growth hormone. The compounds are prepared by substitution of an amino-lactam with a substituted amide function. Growth promoting compositions containing such bezno-fused lactams as the active ingredient thereof are also disclosed. STR1 where L is STR2
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- Effects of varying solvents and of the addition of sulfur on the rate of thiohydrolysis of aromatic nitriles
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Maximal rates of formation of thioamides from m- and p-substituted benzonitriles were obtained by bubbling H2S through solutions of the nitrile in pyridine containing a 0.11 mol fraction of triethylamine or in 95percent ethanol containing about 0.22 mol fraction triethylamine; at other mol fractions the rate fell off sharply.The Hammett p value of +2.3 in pyridine indicates that HS- is the reactive species.The addition of enough sulfur to saturate the solution leads to about a 3-fold enhancement of rate, probably because of the formation of polysulfide ions in trace amounts.
- Abbas, Khamis,Edward, John T.
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p. 3075 - 3078
(2007/10/02)
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- The Loss of ortho Halogeno Substituents From Substituted Thiobenzamide Ions
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The loss of ortho substituents (CH3, Cl, Br, I) from molecular ions of substituted thiobenzamides has been investigated by determination of the critical energy and kinetic energy released during this process to obtain some further insight into the corresponding reaction of N,N-dimethylthiobenzamide ions.In contrast to the latter compounds the ortho methyl substituent is not eliminated from the molecular ions of o-methylthiobenzamide, but the loss of ortho halogeno substituents occurs with identical reaction characteristics in both series of compounds.It is concluded that the loss of halogeno substituents from molecular ions in both series corresponds to a direct substitution reaction via a 4-membered transition state.
- Gruetzmacher, Hans-Fr.
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p. 448 - 450
(2007/10/02)
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