- Efficient synthesis of 2,4-disubstituted thiazoles under grinding
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A simple and convenient protocol is described for the preparation of 2,4-disubstituted thiazoles via a condensation reaction of -halo carbonyl compounds with thiourea or thioacetamide at room temperature, under grinding, in good yields.
- Heravi, Majid M.,Poormohammad, Nargess,Beheshtiha, Yahia S.,Baghernejad, Bita
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Read Online
- Novel oxime derivative as well as preparation method and application thereof
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The invention relates to a novel oxime derivative and a preparation method and application thereof, the novel oxime derivative has a structure as shown in formula (I), Q is optionally substituted phenyl, T is C1-6 alkyl substituted tetrazolyl, and A is th
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Paragraph 0134-0137
(2021/06/22)
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- Gold complex containing diphosphine ortho-position carborane ligand as well as preparation method and application of gold complex
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The invention relates to a gold complex containing a diphosphine ortho-position carborane ligand as well as a preparation method and an application of the gold complex. The gold complex is prepared bythe following method: dropwise adding an n-BuLi solutio
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Paragraph 0032; 0036-0039; 0053-0057
(2020/07/21)
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- Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source
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Methylation of organohalides represents a valuable transformation, but typically requires harsh reaction conditions or reagents. We report a radical approach for the methylation of (hetero)aryl chlorides using nickel/photoredox catalysis wherein trimethyl orthoformate, a common laboratory solvent, serves as a methyl source. This method permits methylation of (hetero)aryl chlorides and acyl chlorides at an early and late stage with broad functional group compatibility. Mechanistic investigations indicate that trimethyl orthoformate serves as a source of methyl radical via β-scission from a tertiary radical generated upon chlorine-mediated hydrogen atom transfer.
- Kariofillis, Stavros K.,Shields, Benjamin J.,Tekle-Smith, Makeda A.,Zacuto, Michael J.,Doyle, Abigail G.
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supporting information
p. 7683 - 7689
(2020/04/22)
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- Computer-Assisted Selective Optimization of Side-Activities—from Cinalukast to a PPARα Modulator
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Automated computational analogue design and scoring can speed up hit-to-lead optimization and appears particularly promising in selective optimization of side-activities (SOSA) where possible analogue diversity is confined. Probing this concept, we employ
- Pollinger, Julius,Schierle, Simone,Neumann, Sebastian,Ohrndorf, Julia,Kaiser, Astrid,Merk, Daniel
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supporting information
p. 1343 - 1348
(2019/07/04)
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- PdII-Catalyzed Regio- and Enantioselective Oxidative C?H/C?H Cross-Coupling Reaction between Ferrocenes and Azoles
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Asymmetric C?H bond functionalization reaction is one of the most efficient and straightforward methods for the synthesis of optically active molecules. Herein we disclose an asymmetric C?H/C?H cross-coupling reaction of ferrocenes with azoles such as oxazoles and thiazoles. Palladium(II)/monoprotected amino acid (MPAA) catalytic system which exhibits excellent reactivity and regioselectivity for oxazoles and thiazoles. This method offers a powerful strategy for constructing planar chiral ferrocenes. Mechanistic studies suggest that the C?H bond cleavage of azoles is likely proceeding through a SEAr process and may not be a turnover limiting step.
- Cai, Zhong-Jian,Liu, Chen-Xu,Gu, Qing,Zheng, Chao,You, Shu-Li
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supporting information
p. 2149 - 2153
(2019/01/24)
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- 2-Amino-4-arylthiazoles through One-Pot Transformation of Alkylarenes with NBS and Thioureas
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Treatment of alkylarenes with N-bromosuccinimide in a mixture of ethyl acetate and water at 60 °C, a mixture of acetonitrile and water at 80 °C, or a mixture of diethyl carbonate and water under irradiation with a tungsten lamp, followed by a reaction with thioureas or arenethioamides provided the corresponding 2-amino- 4-arylthiazoles or 2,4-diarylthiazoles in good to moderate yields, respectively, in one pot. The present reaction is an efficient one-pot transformation method of alkylarenes into 2-amino-4-arylthiazoles and 2,4-diarylthiazoles directly under mild and transition-metal-free conditions.
- Shibasaki, Kaho,Togo, Hideo
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p. 2520 - 2527
(2019/04/04)
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- One-pot NBS-promoted synthesis of imidazoles and thiazoles from ethylarenes in water
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A facile and eco-friendly method has been developed for the synthesis of imidazoles and thiazoles from ethylarenes in water. The reaction proceeds via in situ formation of α-bromoketone using NBS as a bromine source as well as an oxidant, followed by trapping with suitable nucleophiles to provide the corresponding products in good yields under metal-free conditions.
- Chen, Liang,Zhu, Huajian,Wang, Jiang,Liu, Hong
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- One pot synthesis of substituted imidazopyridines and thiazoles from styrenes in water assisted by NBS
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Heating of commercially available styrenes with NBS in water followed by reaction with 2-aminopyridines or thioamides afforded important heterocyclic scaffolds in a one pot procedure. The reaction proceeds via co-oxidant free, in situ formation of α-bromoketone using NBS as a bromine source as well as an oxidant followed by trapping with suitable nucleophiles to provide imidazopyridines and thiazoles.
- Shinde, Mahesh H.,Kshirsagar, Umesh A.
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supporting information
p. 1455 - 1458
(2016/04/04)
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- Access to Thiazole via Copper-Catalyzed [3+1+1]-Type Condensation Reaction under Redox-Neutral Conditions
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A new strategy for thiazoles via copper-catalyzed [3+1+1]-type condensation reaction from oximes, anhydrides and potassiumthiocyanate (KSCN) is developed herein. The transformation has good functional group tolerance and various thiazoles were formed smoothly in good to excellent yields under mild reaction conditions. This process involves copper-catalyzed N-O/C-S bond cleavages, activation of vinyl sp2 C-H bond, and C-S/C-N bond formations which are under redox-neutral conditions as well as operational simplicity.
- Tang, Xiaodong,Yang, Jidan,Zhu, Zhongzhi,Zheng, Meifang,Wu, Wanqing,Jiang, Huanfeng
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p. 11461 - 11466
(2016/11/28)
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- Exploration and Optimization of an Efficient One-pot Sequential Synthesis of Di/tri-substituted Thiazoles from α-Bromoketones, Thioacids Salt, and Ammonium Acetate
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Exploration of scope of an optimized one-pot sequential procedure for preparing of 2,4-di- and 2,4,5-tri-substituted thiazoles has been accomplished. The synthesis was performed by the initial formation of a β-keto-thioester intermediate from nucleophilic substitution of α-bromoketones with thioacid potassium salts, followed by treatment with ammonium acetate and one equivalent of acetic acid in toluene to form imine intermediate eventually leading to cyclization yielding thiazoles. This procedure should be highlighted with a flexible way to control the substitution pattern around thiazole ring by choosing appropriately substituted α-bromoketones even containing acid labile functionality and thioacid potassium salts, and thus its applicability is very wide.
- Venkateswararao, Eeda,Jalani, Hitesh B.,Manoj,, Manickam,Jung, Sang-Hun
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p. 1449 - 1456
(2016/09/24)
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- Synthesis of trisubstituted thiazoles by ligand-free palladium-catalyzed direct 5-arylation of 2,4-disubstituted thiazoles under conventional and microwave-assisted heating
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Trisubstituted thiazoles were synthesized with excellent yields using ligand-free, palladium-catalyzed, direct 5-arylation of 2,4-disubstituted thiazole and conventional or microwave-assisted heating. The palladium-catalyzed reaction yields were significantly influenced by LiCl additive, solvent, and heating method. The reaction times were reduced dramatically by employing microwave radiation instead of conventional heating. The synthetic methods can be applied to diverse 2,4,5-trisubstituted thiazoles by varying the aryl bromide and disubstituted thiazole reactants.
- Kim, Su Kang,Kim, Ji-Hyun,Park, Young Chul,Kim, Jae Won,Yum, Eul Kgun
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p. 10990 - 10995
(2014/01/06)
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- Lipase and deep eutectic mixture catalyzed efficient synthesis of thiazoles in water at room temperature
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Lipase bio-catalyst or ammonium based deep eutectic mixture efficiently catalyzed aqueous phase synthesis of methyl-thiazole and amino-thiazole derivatives. The simple ammonium deep eutectic catalyst, easily synthesized from choline chloride and urea, is inexpensive, recyclable and bio-degradable, making it suitable for industrial applications. Springer Science+Business Media, LLC 2012.
- Lobo, Hyacintha Rennet,Singh, Balvant Shyam,Shankarling, Ganapati Subray
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p. 1369 - 1375
(2013/01/15)
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- A facile and eco-friendly synthesis of diarylthiazoles and diarylimidazoles in water
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A simple, efficient and high yielding greener protocol for the synthesis of substituted thiazoles and imidazoles is described that utilizes the reaction of readily available α-tosyloxy ketones with variety of thioamides/amidines in water.
- Kumar, Dalip,Kumar, N. Maruthi,Patel, Gautam,Gupta, Sudeep,Varma, Rajender S.
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experimental part
p. 1983 - 1986
(2011/04/25)
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- A rapid and high-yielding synthesis of thiazoles and aminothiazoles using tetrabutylammonium salts
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A convenient method for the synthesis of thiazoles and aminothiazoles by treatment of phenacyl bromides with thioamides/thiourea in the presence of tetrabutylammonium hexafluorophosphate (Bu4NPF6) at room temperature was developed. The products having high yields were formed rapidly (within 15 min). The method is simple, rapid and practical, generating thiazole derivatives in excellent isolated yields. The structures of the newly synthesized products were identified by FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analysis data. The Japan Institute of Heterocyclic Chemistry.
- Kocabas, Erdal,Sariguney, Ahmet Burak,Coskun, Ahmet
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experimental part
p. 2849 - 2854
(2011/04/16)
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- Efficient and expeditious synthesis of di- and trisubstituted thiazoles in PEG under catalyst-free conditions
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An efficient and expeditious catalyst-free protocol was developed for the construction of di- and trisubstituted thiazoles from -haloketones and thioureas/thioamides in PEG. The reaction was carried out at ambient temperature, and the products were obtained in excellent isolated yields (91-98%). Additionally, PEG could be recovered easily and was reused without evident loss in activity.
- Zhu, Dongjian,Chen, Jiuxi,Xiao, Huilong,Liu, Miaochang,Ding, Jinchang,Wu, Huayue
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experimental part
p. 2895 - 2906
(2009/12/03)
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- An efficient, catalyst- and solvent-free synthesis of imidazo[1,2-a] pyridines and 2,4-disubstituted thiazoles on grinding
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An efficient synthesis of imidazo[1,2-a]pyridines and 2,4-disubstituted thiazoles in excellent yield under catalyst-and solvent-free conditions at room temperature on grinding has been developed. The important features of this method are that it is reasonably fast, very clean, high yielding, simple workup and environmentally benign.
- Zhu, Dongjian,Chen, Jiuxi,Wu, Dengze,Liu, Miaochang,Ding, Jinchang,Wu, Huayue
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experimental part
p. 84 - 86
(2009/10/15)
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- A facile synthesis of 2,4-disubstituted thiazoles using MnO2
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Structurally diverse thiazoles with electron-donating and electron-withdrawing groups were conveniently synthesized through manganese dioxide (MnO2) oxidation of the corresponding thiazolines. The effect of substitution at the 2- and 4-positions was investigated. The desired thiazoles with aryl or vinyl substitutions at the 2- or 4-position can be obtained in good to excellent yields.
- Yu, Yan-Bo,Chen, Hong-Liang,Wang, Li-Yi,Chen, Xin-Zheng,Fu, Bin
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experimental part
p. 4858 - 4865
(2010/04/05)
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- Discovery and optimization of substituted 1-(1-phenyl-1H-pyrazol-3-yl) methanamines as potent and efficacious type II calcimimetics
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Our efforts to discover potent, orally bioavailable type II calcimimetic agents for the treatment of secondary hyperparathyroidism focused on the development of ring constrained analogues of the known calcimimetic R-568. The structure-activity relationships of various substituted heterocycles and their effects on the human calcium-sensing receptor are discussed. Pyrazole 15 was shown to be efficacious in a rat in vivo pharmacodynamic model.
- Poon, Steve F.,St Jean Jr., David J.,Harrington, Paul E.,Henley III, Charles,Davis, James,Morony, Sean,Lott, Fred D.,Reagan, Jeff D.,Lu, Jenny Ying-Lin,Yang, Yuhua,Fotsch, Christopher
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supporting information; experimental part
p. 6535 - 6538
(2010/04/03)
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- Facile preparation of thiazoles from 1/H-(1′-alkynyl)-5-methyl-1,2,3- benziodoxathiole 3,3-dioxide with thioamides
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Thiazoles were obtained in high yields by the reaction of 1H-1 -(1′-alkynyl)-5-methyl-1,2,3-benziodoxathiole 3,3-dioxides, which were easily prepared from the reaction of 1H-1-hydroxy-5-methyl-1,2,3- benziodoxathiole 3,3-dioxide and 1-alkynes, with thioam
- Ishiwata, Yoshihide,Togo, Hideo
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scheme or table
p. 2637 - 2641
(2009/04/16)
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- Liquid-phase organic synthesis of thiazoles using poly(ethylene glycol)-bound sulfonyl chloride resin
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Reaction of poly(ethylene glycol) (PEG)-bound sulfonic acid with thionyl chloride formed difunctionalized PEG-bound sulfonyl chloride, which was treated with α-hydroxyketones, followed by treatment with thioamides in the presence of potassium carbonate, to afford thiazoles in good yields with a facile workup procedure. Copyright Taylor & Francis Group, LLC.
- Liu, Xiao-Ling,Wang, Qiu-Ying,Sheng, Shou-Ri,Xu, Chen,Cai, Ming-Zhong
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p. 3338 - 3345
(2008/12/22)
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- Efficient synthesis of 2,4-disubstituted thiazoles using ionic liquid?under ambient conditions: a practical approach towards?the?synthesis of Fanetizole
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A highly efficient and rapid synthesis of 2-amino-4-arylthiazoles and 2-methyl-4-arylthiazole from α-bromoketone and thiourea/thioamide is described using room temperature ionic liquid at ambient conditions. The method is simple, rapid and practical, generating thiazole derivatives in excellent isolated yields. This protocol is utilized for a commercially feasible synthesis of an anti-inflammatory agent, Fanetizole.
- Potewar, Taterao M.,Ingale, Sachin A.,Srinivasan, Kumar V.
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p. 11066 - 11069
(2011/05/18)
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- Ring transformations of 1,2,4-dithiazoles: Synthesis and biological studies of novel 5-heterocycles, and their relevant phosphono derivatives
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Reactions of 5-phenyl-3(3H)-thioxo-1,2,4-dithiazole (1) with unsaturated and active phosphonium salts as well as with phosphonates, at r. t. and under the effect of basic catalysis, afforded mainly 1,3,5-dithiazines 5, 12, 17a, 17b, 23a or 23b. Substitute
- Abdou, Wafaa M.,Khidre, Maha D.
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- Synthesis of thiazoles and aminothiazoles from β-keto tosylates under supramolecular catalysis in the presence of β-cyclodextrin in water
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This is the first report on the supramolecular synthesis of thiazoles/aminothiazoles from β-keto tosylates and thioamide/thiourea in water in the presence of β-cyclodextrin in impressive yields. Formation of inclusion complexes was explained from 1H NMR studies. Copyright Taylor & Francis Group, LLC.
- Kumar, V. Pavan,Narender,Sridhar,Nageswar,Rao, K. Rama
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p. 4331 - 4336
(2008/03/13)
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- Efficient conversion of ketones to α-tosyloxyketones with m-chloroperbenzoic acid and p-toluenesulfonic acid in the presence of catalytic amount of IL-supported PhI in [emim]OTs
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Various ketones were smoothly converted into the corresponding α-tosyloxyketones with MCPBA and p-toluenesulfonic acid in the presence of a catalytic amount of ionic-liquid (IL)-supported PhI in room temperature ionic liquid, [emim]OTs. Moreover, the pres
- Akiike, Junnosuke,Yamamoto, Yukiharu,Togo, Hideo
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p. 2168 - 2172
(2008/02/10)
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- Mechanism of dehydration of 2-CH2R-and 2-CHR2-4- hydroxy-Δ2-thiazolines as intermediates in the Hantzsch thiazole synthesis and factors impeding the synthesis of 2-Me-, 2-Ar-, and 2-Het-substituted thiazoles and thiazolo[5,4-b]indoles
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Based on the results of studies of the deuterium exchange and dehydration of 4-hydroxy-Δ2-thiazolines and 2-R-4-acetyl-8b-hydroxy-3a,8b- dihydro-4H-thiazolo[5,4-b]indoles containing the α-methylene (methine) unit at the C(2) atom, the mechanism of dehydration of these compounds generated as intermediates in the Hantzsch synthesis of thiazoles and 2-R-4-acetyl-4H-thiazolo[5,4-b]indoles was proposed. This mechanism includes an additional step of the formation of the corresponding Δ3- thiazolines. According to the results of quantum chemical calculations, this is energetically more favorable than the dehydration in terms of the commonly accepted mechanism. In some cases, an acidic medium impedes the dehydration of 4-hydroxy-Δ2-thiazolines or their cyclic analogs. The proposed mechanism provides an explanation for the empirical data on the differences in the reactivities of both thioamides and α-haloketones, which have remained unexplained in terms of the commonly accepted mechanism. The spontaneous thiazole synthesis is virtually impossible starting from thioamides of aromatic or heteroaromatic acids and α-haloketones bearing electron-withdrawing α substituents or cyclic bromoindoxyl-type haloketones. In the thiazole synthesis from these starting components, it is expedient to perform dehydration under basic catalysis.
- Lepeshkin,Turchin,Gal'Pern,Stankevich,Lyssenko,Velezheva
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p. 1447 - 1455
(2008/09/18)
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- Aqueous phase synthesis of thiazoles and aminothiazoles in the presence of β-cyclodextrin
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A simple and practical procedure for the aqueous phase preparation of thiazoles and aminothiazoles has been developed from phenacyl bromides and thioamide/thiourea in the presence of β-cyclodextrin.
- Narender,Somi Reddy,Sridhar,Nageswar,Rama Rao
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p. 5953 - 5955
(2007/10/03)
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- KINASE INHIBITORS
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The present invention provides kinase inhibitors of Formula I.
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Page/Page column 28
(2010/02/13)
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- Environmentally benign preparation of heteroaromatics from ketones or alcohols, with macroporous polystyrenesulfonic acid and (diacetoxyiodo)benzene, followed by thioamide, amidine, and 2-aminopyridine
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An operationally simple, efficient, and environmentally benign preparation of heteroaromatics such as thiazoles, imidazoles, and imidazo[1,2-a]pyridines from the reactions of a polymer-supported [hydroxy(sulfonyloxy)iodo]benzene (2) with ketones or alcohols, followed by treatment with thioamides, benzamidine, and 2-aminopyridine, respectively, in the presence of potassium carbonate were successfully carried out.
- Ueno, Makoto,Togo, Hideo
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p. 2673 - 2677
(2007/10/03)
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- Novel oxidative α-tosyloxylation of alcohols with iodosylbenzene and p-toluenesulfonic acid and its synthetic use for direct preparation of heteroaromatics
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α-Tosyloxyketones and α-tosyloxyaldehydes were directly prepared from alcohols by treatment with iodosyl-benzene and p-toluenesulfonic acid monohydrate in good yields. This method can be used for the direct preparation of thiazoles, imidazoles, and imidaz
- Ueno, Makoto,Nabana, Takahiro,Togo, Hideo
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p. 6424 - 6426
(2007/10/03)
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- Selective lithiation of 2-methyloxazoles. Applications to pivotal bond constructions in the phorboxazole nucleus
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(equation presented) R = Alkyl, Vinyl, Aryl 6:7 >95:5 The lithiation of 2-methyloxazoles with alkyllithium and hindered lithium amide bases generally results in the competitive formation of a mixture of 5-lithio-and 2-(lithiomethyl)oxazole isomers. Herein a synthetically useful lithiation method which allows for the selective formation of 2-(lithiomethyl)oxazole is described. Diethylamine has been found to be a kinetically competent proton source that will mediate the equilibration of the kinetically formed 5-lithiooxazole to its more stable 2-(lithiomethyl)oxazole counterpart. Application of this metalation strategy with lithium diethylamide to two important bond constructions relevant to a projected phorboxazole synthesis is presented.
- Evans, David A.,Cee, Victor J.,Smith, Thomas E.,Santiago, Keith J.
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- Chameleon catches in combinatorial chemistry: Tebbe olefination of polymer supported esters and the synthesis of amines, cyclohexanones, enones, methyl ketones and thiazoles
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Tebbe olefination of supported esters R1CO2CH2-polymer gave the corresponding vinyl ethers R1C(=CH2)OCH2-polymer which were released, under acidic conditions, to produce methyl ketones R1COMe; by reductive amination, to produce amines R1CH(Me)NHR2; by bromination and reaction of R1CBr(CH2Br)OCH2-polymer with thioureas to produce thiazoles; or, for supported dienyl ethers derived from α,β-unsaturated esters, by Diels-Alder reaction and acid mediated cleavage to produce cyclohexanone derivatives.
- Ball, Christopher P.,Barrett, Anthony G. M.,Commercon, Alain,Compere, Delphine,Kuhn, Cyrille,Roberts, Richard S.,Smith, Marie L.,Venier, Olivier
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p. 2019 - 2020
(2007/10/03)
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- Synthesis of 2-imino-4-thiazolines, 2-imino-4-alkoxythiazolidines, thiazoles and 4-imidazolin-2-ones from α-halomethyl ketimines
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A variety of heterocycles, including 3,4-disubstituted-2-imino-4-thiazolines, 3,4-disubstituted-4-methoxy-2-iminothiazolidines, 2,4-disubstituted-thiazoles, 2-amino-4-substituted-thiazoles and 1,5-disubstituted-4-imidazolin-2-ones, were synthesized from α-chloromethyl and α-bromomethyl ketimines by condensation with potassium thiocyanate, thiourea, ammonium thiocyanate and potassium cyanate.
- De Kimpe, Norbert,De Cock, Wim,Keppens, Marian,De Smaele, Dirk,Meszaros, Andrea
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p. 1179 - 1183
(2007/10/03)
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- A novel thallium(III) - mediated approach to 2-substituted thiazoles from enolizable ketones
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Treatment of thallium (III) p-tolylsulphonate (TTS) with enolizable ketones (1) in refluxing acetonitrile or dioxane followed by addition of thiourea or thioamides provides a novel approach for the synthesis of 2-substituted thiazoles (3).
- Khanna, Mahavir S.,Garg, Chandra P.,Kapoor, Ram P.
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- Synthesis of Unsymmetrical Functionalised Organic Sulphides
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Acyclic thioiminium salts and the condensed thiazolium salts in the presence of aqueous sodium hydroxide as such or under base catalyzed phase transfer catalysis conditions react with appropiate organic halides to provide corresponding unsymmetrical functionalized organic sulphides.With aqueous sodium hydroxide, thioiminium salts provide the disulphides corresponding to incipient thiol.
- Singh, Harjit,Batra, Manohar S.,Singh, Paramjit
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p. 131 - 136
(2007/10/02)
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- Facile Syntheses of 1,4,5-Thiadiazepine, 1,4,7-Thiadiazonine, Imidazothiazine and Pyrimidothiazine
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The condensation of diphenacyl sulphides with hydrazine hydrate, 1,2-diaminoethane, 1,2-diaminopropane and 1,3-diaminopropane, performed in ethylene glycol-ethanol (3: 2) medium provides convenient syntheses of 3,6-diaryl-2,7-dihydro-1,4,5-thiadiazepine (
- Sandhu, S. S.,Tandon, S. S.,Singh, Harjit
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p. 1023 - 1027
(2007/10/02)
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