- Water Mediated Direct Thioamidation of Aldehydes at Room Temperature
-
A mild, greener approach toward thioamide synthesis has been developed. Its unique features include water-mediated reaction with no input energy, additives, or catalysts as well. The presented protocol is attractive with readily available starting materials and the use of different array amines, along with a scaled-up method. Biologically active molecules such as thionicotinamide and thioisonicotinamide can be synthesized from this procedure.
- Gupta, Ankush,Vankar, Jigarkumar K.,Jadav, Jaydeepbhai P.,Gururaja, Guddeangadi N.
-
p. 2410 - 2420
(2022/02/23)
-
- Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions
-
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
-
supporting information
p. 3398 - 3402
(2021/06/25)
-
- Synthesis method of 2-pyridyl-4-methylthiazole-5-formic acid bisabolene ester spice
-
The invention discloses a synthesis method of a 2-pyridyl-4-methylthiazole-5-formic acid bisabolene ester spice. The synthesis method comprises the steps: taking nicotinamide as a starting material, and carrying out a reaction with P2S5 to obtain thionicotinamide; carrying out a cyclization reaction on thionicotinamide and ethyl 2-chloroacetoacetate to obtain 2-pyridyl-4-methylthiazole-5-ethyl formate; hydrolyzing 2-pyridyl-4-methylthiazole-5-ethyl formate to obtain 2-pyridyl-4-methylthiazole-5-formic acid; and under the action of an acid catalyst, synthesizing the 2-pyridyl-4-methylthiazole-5-formic acid bisabolene ester spice at high efficiency. The spice has good antibacterial performance, can resist various bacteria, can be used for animal feeding attraction and cosmetics at the same time, can be used for animal feeding attraction, can increase the palatability and feed intake of poultry, and more importantly can improve the immunity of poultry and reduce the incidence rate; when the spice is used for cosmetics, an antiseptic and antibacterial agent and essence do not need to be added additionally while skin care is conducted, discomfort of sensitive skin is reduced, and the spice has good application prospects.
- -
-
Paragraph 0031-0032
(2020/04/06)
-
- Production method for 2-pyridyl-4-methylthiazole-5-formic acid bisabolene ester spice
-
The invention discloses a production method for synthesizing 2-pyridyl-4-methylthiazole-5-formic acid bisabolene ester spice through solid acid catalysis. The production method comprises the steps: taking nicotinamide as a starting material, and carrying out a reaction with P2S5 to obtain thionicotinamide; carrying out a cyclization reaction on thionicotinamide and ethyl 2-chloroacetoacetate to obtain 2-pyridyl-4-methylthiazole-5-ethyl formate; and hydrolyzing to obtain 2-pyridyl-4-methylthiazole-5-formic acid, condensing with bisabolol under the action of a solid acid catalyst, and carrying out industrial column chromatography separation to efficiently synthesize the 2-pyridyl-4-methylthiazole-5-formic acid bisabolene ester spice.
- -
-
Paragraph 0036-0040; 0052
(2020/04/06)
-
- Synthesis and herbicidal activities of novel thiazole PPO inhibitors
-
Background: Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) is a key enzyme in the biosynthesis of chlorophyll and heme, also the target of different types of herbicides. Thiazole compounds shown excellent biological activity, can be designed by using active groups docking for new PPO inhibitors. Objective: The objective of this study was to synthsize a series of aryl thiazole compounds as PPO inhibitors. Methods: In this study, a series of aryl thiazole compounds derivatives 11a-l were obtained from 2-chloro-5-nitrobenzoic acid as the starting material via esterification, Iron powder reduction, diazoti-zation, Hantzsch reaction and final acylation. All synthesized compounds have been tested for their herbicidal activities as a PPO inhibitors. Results: The Petri dish test indicated that all compounds exhibited good herbicidal activities at 200 mg/L using culture dish. And the post-emergence tests showed that at 150g.ai/ha on weed stem leaf spray treatment, some of the title compounds exhibited 80% inhibition rate against the dicotyle-donou weeds Amaranthus retroflexus and Eclipta prostrate. Conclusion: Good activity was noted for some compounds that compounds 11a, 11b, 11c, 11g, 11h had 80% inhibition on stems and leaves of Amaranthus retroflexus at 150g.ai/ha.
- Chen, Shu,Liu, Jie,Pei, Dan,Ren, Guihua,Shi, Jianjun,Tan, Chengxia,Xu, Tianming,Yang, Ren,Zhang, Donglin,Zhang, Fan
-
p. 192 - 198
(2020/02/29)
-
- Potent ribonucleotide reductase inhibitors: Thiazole-containing thiosemicarbazone derivatives
-
The antioxidant, antimalarial, antibacterial, and antitumor activities of thiosemicarbazones have made this class of compounds important for medicinal chemists. In addition, thiosemicarbazones are among the most potent and well-known ribonucleotide reductase inhibitors. In this study, 24 new thiosemicarbazone derivatives were synthesized, and the structures and purity of the compounds were determined by IR, 1H NMR, 13C NMR, mass spectroscopy, and elemental analysis. The IC50 values of these 24 compounds were determined with an assay for ribonucleotide reductase inhibition. Compounds 19, 20, and 24 inhibited ribonucleotide reductase enzyme activity at a higher level than metisazone as standard. The cytotoxic effects of these compounds were measured on the MCF7 (human breast adenocarcinoma) and HEK293 (human embryonic kidney) cell lines. Similarly, compounds 19, 20, and 24 had a selective effect on the MCF7 and HEK293 cell lines, killing more cancer cells than cisplatin as standard. The compounds (especially 19, 20, and 24 as the most active ones) were then subjected to docking experiments to identify the probable interactions between the ligands and the enzyme active site. The complex formation was shown qualitatively. The ADME (absorption, distribution, metabolism, and excretion) properties of the compounds were analyzed using in-silico techniques.
- Ertas, Merve,Sahin, Zafer,Bulbul, Emre F.,Bender, Ceysu,Biltekin, Sevde N.,Berk, Barkin,Yurttas, Leyla,Nalbur, Aysu M.,Celik, Hayati,Demirayak, ?eref
-
-
- Aryl bithiazole compound and application
-
The invention discloses an aryl bithiazole compound and application. A series of aryl bithiazole compounds are prepared in the invention, and application of the compounds is researched. According to biological activity test results, the aryl bithiazole compound provided by the invention has excellent herbicidal activity, has wide herbicide controlling spectrum to wheat, sorghum, barnyard grass, cucumber, oilseed rapes and radish, has a high inhibition rate on broadleaf weeds, and particularly has obvious inhibitory effects on amaranthus retroflexus and eclipta prostrate.
- -
-
Paragraph 0044; 0045
(2019/01/06)
-
- A efficient protocol for the synthesis of thioamides in [DBUH][OAc] at room temperature
-
A novel, simple and eco-friendly method to synthesize thioamides from aryl nitriles and sodium sulfide (Na2S·9H2O) catalyzed by 1,8-diazabicyclo[5,4,0]undec-7-enium acetate ([DBUH][OAc]) ionic liquid (IL) at room temperature was developed in this paper. In this reaction, readily available inorganic salt (Na2S·9H2O) serves as the sulfur source, and various functional groups of aryl nitriles were well tolerated at room temperature. In addition, the products were easily separated from the IL which could be reused at least five times without considerable loss of its activity and applied in the green, concise synthesis of ethionamide.
- Cao, Xian-Ting,Qiao, Li,Zheng, Hui,Yang, Hui-Yong,Zhang, Peng-Fei
-
p. 170 - 175
(2018/01/17)
-
- A simple method for synthesis of thioamides and application in synthesis of 1,2,4-thiadiazoles
-
A novel, simple protocol is disclosed for the synthesis of 1,2,4-thiadiazoles starting from thioamides with Na2-eosin Y-sensitized titanium dioxide as catalyst through visible light irradiation (7 W blue LED light) and only 0.3 mol% catalysts were used. The raw material thioamides is prepared by aryl nitriles and sodium sulfide (Na2S9H2O) in DMF and in this reaction, readily available, inexpensive inorganic salt (Na2S9H2O) serves as the sulfur source and various functional groups of aryl nitriles were well and thioamides were synthesized successfully in gram-scale.
- Cao, Xian Ting,Yang, Huiyong,Zheng, Hui,Zhang, Pengfei
-
p. 509 - 517
(2018/03/27)
-
- Thiophosphate - A Versatile Prebiotic Reagent?
-
Described are our preliminary studies on the reactivity of thiophosphate in a setting which correlates with the cyanosulfidic systems chemistry we have previously reported. Thiophosphate adds to various nitrile groups giving the corresponding thioamides in a highly efficient manner and the mechanistic implications are briefly discussed. Thiophosphate can also act as a phosphorylating agent, which was demonstrated with adenosine. The prebiotic availability of thiophosphate must be questioned, but if a plausible synthesis can be found, the advantages it would bring to the field of prebiotic chemistry appear to be highly beneficial.
- Ritson, Dougal J.,Xu, Jiangfeng,Sutherland, John D.
-
-
- Synthesis and antitubercular activity of new 1,3,4-oxadiazoles bearing pyridyl and thiazolyl scaffolds
-
In search of more potent and safe new antitubercular agents, here new 2-pyridinyl substituted thiazolyl-5-aryl-1,3,4-oxadiazoles (6a–o), have been designed and synthesized using thionicotinamide as a starting, following novel multistep synthetic route. An intermediate, pyridinyl substituted thiazolyl acid hydrazide (4) when condensed with benzoic acids/nicotinic acids (5a–o) in the presence of silica supported POCl3yielded better to excellent yields of the title compounds. All the synthesized compounds (6a–o) and intermediate acid hydrazide (4) have been screened for their in vitro antitubercular activity against Mycobacterium tuberculosis H37Ra (MTB) and Mycobacterium bovis BCG. Amongst them, 6f, 6j, 6l and 6o have revealed promising activity against M. bovis BCG at concentrations less than 3?μg/mL. These compounds have shown low cytotoxicity (CC50: >100?μg/mL) towards four human cancer cell lines. Molecular docking study has also been performed against mycobacterial enoyl reductase (InhA) enzyme to gain an insight into the binding modes of these molecules and recorded good binding affinity. The ADME properties the title products have also been analyzed.
- Dhumal, Sambhaji T.,Deshmukh, Amarsinh R.,Bhosle, Manisha R.,Khedkar, Vijay M.,Nawale, Laxman U.,Sarkar, Dhiman,Mane, Ramrao A.
-
supporting information
p. 3646 - 3651
(2016/07/21)
-
- Modification of organic compounds with Lawesson's reagent
-
Application in organic synthesis of Lawesson's reagent, 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide, provides a possibility to replace an oxygen atom for a sulfur atom in the carbonyl group of ketones, esters, amides, in ether group, and also either to induce a rearrangement of the initial structure of organic compounds with or without inclusion of sulfur atoms or to lead to the formation of various types of organophosphorus compounds. The formed organosulfur compounds exhibit a wide range of biological action.
- Kayukova,Praliyev,Gut'Yar,Baitursynova
-
p. 148 - 160
(2015/04/14)
-
- From liquid to solid-state fluorescence: Tricyclic lactones based on 4-hydroxy-1,3-thiazoles
-
This work describes the synthesis of a series of tricyclic lactones based on 4-hydroxy-1,3-thiazoles prepared by the classic Hantzsch synthesis. The tricyclic lactones are more rigid than the parent 4-hydroxythiazoles and are featured not only by fluorescence in solution, but also in the solid state. An extension of the chromophoric system was successfully realized by integration of the benzothiazole substructure, thus resulting in bathochromic shifts of absorption and also fluorescence. The new synthesized lactones additionally show interesting properties in solution, whereby the initial blue fluorescence changes dramatically with a variation of the pH value. Georg Thieme Verlag Stuttgart · New York.
- Calderón Ortiz, Lorena K.,Würfel, Hendryk,T?uscher, Eric,Wei, Dieter,Birckner, Eckhard,G?rls, Helmar,Beckert, Rainer
-
p. 126 - 134
(2014/01/06)
-
- INSECTICIDALLY ACTIVE PYRIDYL-THIAZOLE AND PYRIDYL-THIADIAZOLE DERIVATIVES
-
Compounds of formula (I), wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts and all stereoisomers and tautomeric forms of the compounds of formula (I) can be used as insecticides and can be prepared in a manner known per se.
- -
-
Page/Page column 31-32
(2013/03/26)
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- Optimizing thiadiazole analogues of resveratrol versus three chemopreventive targets
-
Chemoprevention is an approach to decrease cancer morbidity and mortality through inhibition of carcinogenesis and prevention of disease progression. Although the trans stilbene derivative resveratrol has chemopreventive properties, its action is compromised by weak non-specific effects on many biological targets. Replacement of the stilbene ethylenic bridge of resveratrol with a 1,2,4-thiadiazole heterocycle and modification of the substituents on the two aromatic rings afforded potential chemopreventive agents with enhanced potencies and selectivities when evaluated as inhibitors of aromatase and NF-κB and inducers of quinone reductase 1 (QR1).
- Mayhoub, Abdelrahman S.,Marler, Laura,Kondratyuk, Tamara P.,Park, Eun-Jung,Pezzuto, John M.,Cushman, Mark
-
experimental part
p. 510 - 520
(2012/03/10)
-
- A THIONATION PROCESS AND A THIONATING AGENT
-
A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N
- -
-
Page/Page column 13
(2012/08/27)
-
- A thionation process and a thionating agent
-
A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N.
- -
-
Page/Page column 8
(2012/08/14)
-
- Thionations using a P4S10-pyridine complex in solvents such as acetonitrile and dimethyl sulfone
-
Tetraphosphorus decasulfide (P4S10) in pyridine has been used as a thionating agent for a long period of time. The moisture-sensitive reagent has now been isolated in crystalline form, and the detailed structure has been determined by X-ray crystallography. The thionating power of this storable reagent has been studied and transferred to solvents such as acetonitrile in which it has proven to be synthetically useful and exceptionally selective. Its properties have been compared with the so-called Lawesson reagent (LR). Particularly interesting are the results from thionations at relatively high temperatures (165 °C) in dimethyl sulfone as solvent. Under these conditions, for instance, acridone and 3-acetylindole could quickly be transformed to the corresponding thionated derivatives. Glycylglycine similarly gave piperazinedithione. At these temperatures, LR is inefficient due to rapid decomposition. The thionated products are generally cleaner and more easy to obtain because in the crystalline reagent, impurities which invariably are present in the conventional reagents, P4S 10 in pyridine or LR, have been removed. 2011 American Chemical Society.
- Bergman, Jan,Pettersson, Birgitta,Hasimbegovic, Vedran,Svensson, Per H.
-
experimental part
p. 1546 - 1553
(2011/06/11)
-
- Solvent-free synthesis of 3,5-di(hetero)aryl-1,2,4-thiadiazoles by grinding of thioamides under oxidative conditions
-
An efficient and facile synthesis of 3,5-di(hetero)aryl-1,2,4-thiadiazoles by oxidative dimerisation of thioamides by grinding with NBS under solvent-free conditions at room temperature has been developed. The efficiency of this reaction was demonstrated by the compatibility with trifluoromethyl, methyl, methoxy, chloro, pyridyl and thienyl groups. This method has notable advantages in terms of short reaction times, high yields and is a more practical alternative to the existing methods to access these compounds.
- Xu, Yali,Chen, Jiuxi,Gao, Wenxia,Jin, Huile,Ding, Jinchang,Wu, Huayue
-
experimental part
p. 151 - 153
(2010/08/06)
-
- Efficient and green protocol for the synthesis of thioamides in C 6 (mim)2Cl2 as a dicationic ionic liquid
-
A simple, efficient, facile and eco-friendly process for the synthesis of thioamides from nitriles using 1,6-bis(3methylimidazolium-1-yl)hexane chloride [C6(mim)2Cl2] as a dicationic ionic liquid (DIL) was developed. The ionic liquid was easily separated from the reaction mixture and was recycled at least four times without any loss of its activity.
- Khosropour,Noei,Mirjafari
-
experimental part
p. 752 - 758
(2010/11/04)
-
- A mild and versatile synthesis of thioamides
-
Aliphatic and aromatic nitriles react with thioacetic acid in the presence of calcium hydride to give the corresponding thioamides in good to excellent yields. The examples studied include haloaryl nitriles in which the halogen is facile towards SNAr reactions under other conditions. Georg Thieme Verlag Stuttgart.
- Mahammed,Jayashankara,Premsai Rai,Mohana Raju,Arunachalam
-
experimental part
p. 2338 - 2340
(2009/12/08)
-
- Expeditious microwave-assisted thionation with the system PSCl 3/H2O/Et3N under solvent-free condition
-
(Chemical Equation Presented) A novel thionation protocol for carbonyl compounds, with the system PSCl3/H2O/Et3N has been discovered. Clean, rapid, and efficient synthesis of a variety of thiocarbonyl compounds such as thioamides, thiolactams, thioketones, thioxanthones, and thioacridone can be achieved through this simple and convenient method under solventless condition with microwave irradiation.
- Pathak, Uma,Pandey, Lokesh Kumar,Tank, Rekha
-
p. 2890 - 2893
(2008/09/19)
-
- Synthesis and application of a fluorous Lawesson's reagent: Convenient chromatography-free product purification
-
A fluorous analogue of Lawesson's reagent for thionation of carbonyl compounds has been developed and its use demonstrated on a series of amides, esters, and ketones. The separation of the Lawesson's reagent-derived byproducts can be achieved by a simple fluorous solid-phase extraction.
- Kaleta, Zoltan,Tarkanyi, Gabor,Goemoery, Agnes,Kalman, Ferenc,Nagy, Tamas,Soos, Tibor
-
p. 1093 - 1095
(2007/10/03)
-
- Synthesis of aromatic thioamide from nitrile without handling of gaseous hydrogen sulfide
-
A new method for synthesizing aromatic primary thioamides is described. Simple treatment of aromatic nitriles with sodium hydrogen sulfide and magnesium chloride in dimethylformamide (DMF) gave aromatic primary thioamides in yields of 80-99% without handling of hazardous hydrogen sulfide.
- Manaka, Akira,Sato, Masakazu
-
p. 761 - 764
(2007/10/03)
-
- Simple microwave-assisted method for the synthesis of primary thioamides from nitriles
-
Primary thioamides are prepared in excellent yield from the corresponding nitrile by treatment with ammonium sulfide in methanol, at room temperature for electron-deficient aromatic nitriles or under microwave irradiation at 80 °C or 130 °C in 15-30 minutes for other aromatic and aliphatic nitriles. This procedure avoids the use of gaseous H2S under high pressure, proceeds in the absence of base and provides thioamides usually without the need for chromatographic purification.
- Bagley, Mark C.,Chapaneri, Krishna,Glover, Christian,Merritt, Eleanor A.
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p. 2615 - 2617
(2007/10/03)
-
- Thionation with the reagent combination of phosphorus pentasulfide and hexamethyldisiloxane
-
The combination of P4S10 and hexamethyldisiloxane efficiently converts esters, lactones, amides, lactams, and ketones to their corresponding thiono derivatives. In the presence of elemental sulfur, 3-oxoesters are converted to dithiolethiones by this reagent. Yields are comparable to or superior to those obtained with Lawesson's reagent. The method has the advantage that reagent-derived byproducts may be removed by a simple hydrolytic workup or by filtration through silica gel, rather than by chromatography, as required for Lawesson's reagent.
- Curphey, Thomas J.
-
p. 6461 - 6473
(2007/10/03)
-
- Synthesis of primary thioamides from nitriles and hydrogen sulfide catalyzed by anion-exchange resin
-
A new method has been developed for converting nitriles into primary thioamides. Treatment of various nitriles (Table 1, entries 1-12) with gaseous hydrogen sulfide in a mixture of methanol-water or ethanol-water and in the presence of anion-exchange resin (Dowex 1X8, SH- form) at room temperature and ambient pressure gave the corresponding thioamides in 25-96% yield.
- Liboska, Radek,Zyka, Daniel,Bobek, Miroslav
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p. 1649 - 1651
(2007/10/03)
-
- Design and synthesis of sulfonyl-substituted 4,5-diarylthiazoles as selective cyclooxygenase-2 inhibitors
-
A series of novel sulfone substituted 4,5-diarylthiazoles have been synthesized and evaluated for their inhibition of the two isoforms of human cyclooxygenase (COX-1 and COX-2). This series displays exceptionally selective COX-2 inhibition.
- Carter, Jeffery S.,Rogier,Graneto, Matthew J.,Seibert, Karen,Koboldt, Carol M.,Zhang, Yan,Talley, John J.
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p. 1167 - 1170
(2007/10/03)
-
- Conformations and Rotational Barriers in NADH and NAD+ Analogues. A Dynamic NMR and Molecular Mechanics Investigation
-
The conformational preferences and rotational barriers about both the ring-amide bond and the C-N bond in NADH and NAD+ analogues have been investigated by dynamic NMR spectroscopy and molecular mechanics calculations with the intention to clarify the stereodynamic situation in these types of cross-conjugated amide.The results can be summarized as follows. (i) The primary amides an thioamides are planar or nearly planar and possess ring-amide barriers (ΔG ca. 4-7 kcal mol-1) over the 90 deg twisted state. (ii) The cis conformation is strongly preferred for NADH analogues, but in the indole analogue 6b the two conformations differ by only ca. 0.3 kcal mol-1. (iii) The tertiary amides are twisted in the ground state and have steric barriers (ΔG=6-10 kcal mol-1) over the planar state. (iv) The C-N barriers are considerably larger, (ΔG=11-17 kcal mol-1 for amides, and 12-21 kcal mol-1 for thioamides). (v) The barrier heights are governed by the efficiency of the cross-conjugation in the ground and transition states, and by the steric interactions in the planar conformations.The exchange process observed in NMR for NADH by Redfield et al. is due to C-N rotation and not to amide group rotation.
- Berg, Ulf,Astroem, Nina
-
p. 599 - 608
(2007/10/02)
-
- A REMARKABLY SIMPLE CONVERSION OF NITRILES TO THIOAMIDES
-
Thiolacetic acid and light smoothly convert nitriles to thioamides.
- Gauthier, Jacques Yves,Lebel, Helene
-
p. 325 - 326
(2007/10/02)
-
- A new method for converting nitriles into primary thioamides by sodium trimethylsilanethiolate
-
A new method was developed for converting nitriles into primary thioamides. Treatment of various nitriles 1 with 1.5-2.5 equivalents of sodium trimethylsilyl sulfide (sodium trimethylsilanethiolate) in 1,3-dimethyl-2-imidazolidinone at 20-35°C for 4-30 hours gave the corresponding thioamides 2 in 27-80% yield.
- Lin,Ku,Shiao
-
p. 1219 - 1220
(2007/10/02)
-