- Pleuromutilin derivative with 1, 3, 4-oxadiazole side chain and preparation and application thereof
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The invention belongs to the field of medicinal chemistry, and particularly relates to a pleuromutilin derivative with a 1, 3, 4-oxadiazole side chain and preparation and application thereof The pleuromutilin derivative with the 1, 3, 4-oxadiazole side chain is a compound shown in a formula 2 or a pharmaceutically acceptable salt thereof, and a solvent compound, an enantiomer, a diastereoisomer and a tautomer of the compound shown in the formula 2 or the pharmaceutically acceptable salt thereof or a mixture of the solvent compound, the enantiomer, the diastereoisomer and the tautomer in any proportion, including a racemic mixture. The pleuromutilin derivative has good antibacterial activity, is especially suitable for being used as a novel antibacterial agent for systemic system infection of animals or human beings, and has good water solubility.
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Paragraph 0055-0056; 0070; 0090; 0092; 0095; 0103
(2021/07/24)
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- Design, synthesis and acaricidal activities of Cyflumetofen analogues based on carbon-silicon isosteric replacement
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The application of a carbon-silicon bioisosteric replacement strategy to find new acaricides with improved properties led to the discovery of Sila-Cyflumetofen 6B, a novel and highly potent acaricide. The essential t-butyl group in the beta-ketonitrile ac
- Beadle, Ryan,Cheng, Jiagao,Earley, Fergus G.,Li, Zhong,Maienfisch, Peter,Zhou, Cong
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- Synthesis and bioactivity of sulfide derivatives containing 1,3,4-oxadiazole and pyridine
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A series of novel sulfide derivatives containing 1,3,4-oxadiazole and pyridine were synthesized, characterized, and tested for their antibacterial activity against tobacco bacterial wilt and rice bacterial blight and for insecticidal activity toward diamondback moth. The results showed that some compounds had good insecticidal and bactericidal activity, e.g., the activities of compounds 6e and 6g–6j toward tobacco bacterial wilt were much better than those of commercial thiodiazole-copper, and some of the synthesized compounds possessed good insecticidal activity against Plutella xylostella. Compounds 6d, 6h, 6j, 6l, 6p, 6r, and 6p displayed over 93% activity at 500 mg L? 1.
- Yu, Gang,Chen, Shunhong,He, Feng,Luo, Dexia,Zhang, Yu,Wu, Jian
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p. 1075 - 1085
(2019/09/10)
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- Design, synthesis, insecticidal activity and 3D-QSR study for novel trifluoromethyl pyridine derivatives containing an 1,3,4-oxadiazole moiety
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A series of trifluoromethyl pyridine derivatives containing 1,3,4-oxadiazole moiety was designed, synthesized and bio-assayed for their insecticidal activity. The result of bio-assays indicated the synthesized compounds exhibited good insecticidal activity against Mythimna separata and Plutella xylostella, most of the title compounds show 100% insecticidal activity at 500 mg L-1 and >80% activity at 250 mg L-1 against the two pests. Compounds E18 and E27 showed LC50 values of 38.5 and 30.8 mg L-1 against Mythimna separata, respectively, which were close to that of avermectin (29.6 mg L-1); compounds E5, E6, E9, E10, E15, E25, E26, and E27 showed 100% activity at 250 mg L-1, which were better than chlorpyrifos (87%). CoMFA and CoMSIA models with good predictability were proposed, which revealed the electron-withdrawing groups with an appropriate bulk at 2- and 4-positions of benzene ring could enhance insecticidal activity.
- Xu,Wang,Luo,Yu,Guo,Fu,Zhao,Wu
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p. 6306 - 6314
(2018/02/19)
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- SO2F2-Mediated One-Pot Synthesis of Aryl Carboxylic Acids and Esters from Phenols through a Pd-Catalyzed Insertion of Carbon Monoxide
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A one-pot Pd-catalyzed carbonylation of phenols into their corresponding aryl carboxylic acids and esters through the insertion of carbon monoxide has been developed. This procedure offers a direct synthesis of aryl carboxylic acids and esters from inexpensive and abundant starting materials (phenols, SO2F2 and CO) under mild conditions. This method tolerates a broad range of functional groups and is also applicable for the modification of complicated natural products.
- Fang, Wan-Yin,Leng, Jing,Qin, Hua-Li
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p. 2323 - 2331
(2017/09/06)
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- Noncovalent Interactions in Ir-Catalyzed C-H Activation: L-Shaped Ligand for Para-Selective Borylation of Aromatic Esters
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An efficient strategy for the para-selective borylation of aromatic esters is described. For achieving high para-selectivity, a new catalytic system has been developed modifying the core structure of the bipyridine. It has been proposed that the L-shaped ligand is essential to recognize the functionality of the oxygen atom of the ester carbonyl group via noncovalent interaction, which provides an unprecedented controlling factor for para-selective C-H activation/borylation.
- Hoque, Md Emdadul,Bisht, Ranjana,Haldar, Chabush,Chattopadhyay, Buddhadeb
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supporting information
p. 7745 - 7748
(2017/06/21)
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- Cyclic-Protected Hexafluoroacetone as an Air-Stable Liquid Reagent for Trifluoromethylations
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An air-stable liquid trifluoromethylating reagent is readily synthesized from gaseous hexafluoroacetone and 2-methylproline on a gram scale. The reaction of the trifluoromethylating reagent with tert-butoxy cuprate K[Cu(OtBu)2] leads to the CuCF3in high yield. This species is directly formed from the tetrahedral cuprate intermediate through intramolecular migration of the trifluoromethyl group to copper. The CuCF3reagent prepared in situ by our method can be used for the trifluoromethylation of aryl iodides, arylboronic acids, and terminal alkynes in good to excellent yields, even on a gram scale. Furthermore, the CuC2F5reagent can be prepared in the same way, and this can be used in the pentafluoroethylation of arylboronic acids or aryl bromides in good to excellent yields.
- Negishi, Kazuyuki,Aikawa, Kohsuke,Mikami, Koichi
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p. 4099 - 4104
(2016/08/24)
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- Trifluorolactic demethylating agent powder, its manufacturing method using the same and method of manufacturing a trifluoromethyl group-containing compound
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PROBLEM TO BE SOLVED: To provide a trifluoromethylation agent powder stable at room temperature and useful as a reaction reagent and a production method thereof, and a production method of trifluoromethyl group-containing compound.SOLUTION: A zinc powder is reacted with a trifluoromethyl iodide in a N,N-dimethylformamide solvent, and it is filtrated and concentrated to obtain a trifluoromethylation agent powder represented by general formula (1) that is (CF)ZnI (DMPU)(1), where DMPU represents N,N-dimethyl propylene urea and n represents an integer of 1 to 4, then it is reacted with substituted aromatic iodide in a presence of copper (I) catalyst to obtain a trifluoromethyl group-containing compound.
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Paragraph 0033
(2017/03/14)
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- A pharmaceutical intermediate trifluoromethyl substituted arene the synthetic method of the compound of
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The invention relates to a method for synthesizing a medical intermediate trifluoromethyl substituted aromatic compound shown in a formula (I). The structural formula is as shown in the specification. The method comprises the following steps: adding a formula shown in a formula (II), a formula shown in a formula (III), a catalyst and alkali into an organic solvent at room temperature in a shading mode, heating to the temperature of 30-40 DEG C, and stirring for 20-30 minutes; adding an accelerant, heating to the temperature of 70-80 DEG C, carrying out heat preservation reaction and stirring reaction for 3-5 hours, thereby obtaining the compound shown in the formula (I), wherein the structural formula is as shown in the specification, and R refers to C1-C6 alkyl, cyano, halogens or ester groups. According to the trifluoromethylation method of the aromatic compound, the specific reaction substrate, catalyst, alkali, accelerant and organic solvent are adopted in the method, and good area location property is obtained by virtue of mutual coordination of the factors, so that the trifluoromethyl is introduced into a specific position (ortho-position of the substituted aromatic compound) at high yield, high yield is achieved, and the method has good research value and application potential.
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Paragraph 0041-0044
(2017/03/08)
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- METHOD FOR PRODUCING 2-TRIFLUOROMETHYL BENZOIC ACID ESTER
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PROBLEM TO BE SOLVED: To provide a method for obtaining a 2-trifluoromethyl benzoic acid ester by a simple, efficient, and industrially excellent method using a starting substrate and a reagent which are inexpensive and industrially available without passing through an expensive synthetic intermediate. SOLUTION: The method for producing 2-trifluoromethyl benzoic acid ester represented by the following formula where n is an integer of 1-4 comprises: converting 2-halogen-substituted benzotrifluoride to a Grignard reagent; reacting the Grignard reagent with dialkyl carbonate; and subsequently subjecting to hydrolysis treatment. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0045-0048; 0050
(2017/03/24)
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- Synthesis, characterization and keto-enol tautomerism of novel 2-(trifluoromethyl)benzohydrazide derivatives
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A series of novel 2-(trifluoromethyl)benzohydrazide derivatives were synthesized starting from 2,2,2-trifluoromethyl benzoic acid in three consecutive steps by using hydrazine hydride and aldehydes at room temperature. In above methodology a total of 21 n
- Navudu, Ramesh,Mannem, Gangadhara Rao,Bollikolla, Hari Babu
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p. 1351 - 1360
(2016/04/08)
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- BIS(TRIFLUOROMETHYL)ZINC DMPU COMPLEX, MANUFACTURING METHOD THEREOF AND MANUFACTURING METHOD OF TRIFLUOROMETHYL GROUP-CONTAINING COMPOUND USING THE SAME
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PROBLEM TO BE SOLVED: To provide a bis(trifluoromethyl)zinc DMPU complex stable under room temperature and useful as a reaction reagent, a manufacturing method thereof and a manufacturing method of a trifluoromethyl group-containing compound using the same. SOLUTION: A method of obtaining a trifluoromethyl group-containing compound by reacting with a substituted aromatic iodide under a copper (I) catalyst after obtaining a bis(fluoromethyl)zinc DMPU complex represented by the formula (1) (CF3)2Zn (DMPU)2 (1), where DMPU represents N,N'-dimethyl propylene urea, by reacting dialkyl zinc, trifluoromethyl halide and N,N'-dimethyl propylene urea in an organic solvent, then filtration or solvent leaving removal of precipitate. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0027; 0028
(2018/11/22)
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- Copper-Promoted Trifluoromethanesulfonylation and Trifluoromethylation of Arenediazonium Tetrafluoroborates with NaSO2CF3
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A tunable chemoselective trifluoromethanesulfonylation and trifluoromethylation of arenediazonium tetrafluoroborates with Langlois' reagent (NaSO2CF3) was developed. The Cu2O-catalyzed reaction in DMSO gave aryl trifluoromethanesulfones as the major products. On the other hand, the trifluoromethylated arenes were produced in the presence of oxidant tert-butyl hydroperoxide, CuBF4(MeCN)4, and 2,2′;6′,2 terpyridine (tpy). Both of these transformations proceed under mild conditions and tolerate functional groups.
- Zhang, Ke,Xu, Xiu-Hua,Qing, Feng-Ling
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p. 7658 - 7665
(2015/08/18)
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- Stable but reactive perfluoroalkylzinc reagents: Application in ligand-free copper-catalyzed perfluoroalkylation of aryl iodides
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The aromatic perfluoroalkylation catalyzed by a copper(I) salt with bis(perfluoroalkyl)zinc reagents Zn(RF)2(DMPU)2, which were prepared and then isolated as a stable white powder from perfluoroalkyl iodide and diethylzinc, was accomplished to provide the perfluoroalkylated products in good-to-excellent yields. The advantages of this reliable and practical catalytic reaction are 1) airstable and easy-to-handle bis(perfluoroalkyl)zinc reagents can be utilized, 2) the reagent is reactive and hence the operation without activators and ligands is simple, and 3) not only trifluoromethylation but also perfluoroalkylation can be attained.
- Aikawa, Kohsuke,Nakamura, Yuzo,Yokota, Yuki,Toya, Wataru,Mikami, Koichi
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supporting information
p. 96 - 100
(2015/02/05)
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- Silver-Catalyzed C-H Trifluoromethylation of Arenes Using Trifluoroacetic Acid as the Trifluoromethylating Reagent
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Direct trifluoromethylation of arenes using TFA as the trifluoromethylating reagent was achieved with Ag as the catalyst. This reaction not only provides a new protocol for aryl C-H trifluoromethylation, but the generation of CF3· from TFA may prove useful in other contexts and could potentially be extended to other trifluoromethylation reactions. (Chemical Equation Presented).
- Shi, Guangfa,Shao, Changdong,Pan, Shulei,Yu, Jingxun,Zhang, Yanghui
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supporting information
p. 38 - 41
(2015/07/28)
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- New Reagent for Highly Efficient Synthesis of Trifluoromethyl-Substituted Arenes and Heteroarenes
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A new reagent trimethylsilyl chlorodifluoroacetate (TCDA) is reported for the introduction of a -CF3 group to arenes and heteroarenes. Compared with current known reagents, TCDA shows very broad scope with respect to electron-deficient, -neutral, and -rich aryl/heteroaryl iodides as well as excellent functional group tolerance, including ester, amide, aldehyde, hydroxyl, and carboxylic acid. (Chemical Equation Presented).
- Zhang, Xiaomin,Wang, Jian,Wan, Zehong
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supporting information
p. 2086 - 2089
(2015/05/13)
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- Conversion of aromatic amino into trifluoromethyl groups through a Sandmeyer-type transformation
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A novel strategy for aromatic trifluoromethylation by converting amino into trifluoromethyl groups via a Sandmeyer-type reaction is reported. The transformation involves diazotization of the aromatic amines with tert-butyl nitrite and hydrochloric acid to form aryldiazonium chlorides, followed by trifluoromethylation with trifluoromethylsilver at low temperature. Various readily available aromatic amines are smoothly converted under mild conditions. Georg Thieme Verlag Stuttgart. New York.
- Wang, Xi,Xu, Yan,Zhou, Yujing,Zhang, Yan,Wang, Jianbo
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supporting information
p. 2143 - 2148
(2014/08/18)
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- Silver-mediated trifluoromethylation of aryldiazonium salts: Conversion of amino group into trifluoromethyl group
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A novel strategy for aromatic trifluoromethylation by converting aromatic amino group into CF3 group is reported herein. This method, which can be considered as trifluoromethylation variation of the classic Sandmeyer reaction, uses readily available aromatic amines as starting materials and is performed under mild conditions.
- Wang, Xi,Xu, Yan,Mo, Fanyang,Ji, Guojing,Qiu, Di,Feng, Jiajie,Ye, Yuxuan,Zhang, Songnan,Zhang, Yan,Wang, Jianbo
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supporting information
p. 10330 - 10333
(2013/08/23)
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- Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide
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The trifluoromethylation of aryl iodides catalyzed by copper(I) salt with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide and Zn dust was accomplished. The catalytic reactions proceeded under mild reaction conditions, providing th
- Nakamura, Yuzo,Fujiu, Motohiro,Murase, Tatsuya,Itoh, Yoshimitsu,Serizawa, Hiroki,Aikawa, Kohsuke,Mikami, Koichi
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p. 2404 - 2409
(2014/01/06)
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- Direct synthesis of a trifluoromethyl copper reagent from trifluoromethyl ketones: Application to trifluoromethylation
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Being economic with fluorine: The direct synthesis of CuCF3 from a cuprate reagent and trifluoromethyl ketones, as one of the most economical and efficient trifluoromethyl sources, was accomplished. The advantages of this method are all of reagents employed are low-cost, operation is simple, and the yield of CuCF3 is virtually quantitative (see scheme). Furthermore, three types of trifluoromethylations smoothly proceeded to provide the corresponding products in high yields. Copyright
- Serizawa, Hiroki,Aikawa, Kohsuke,Mikami, Koichi
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supporting information
p. 17692 - 17697
(2014/01/17)
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- Copper-catalyzed arylation of 1 H-perfluoroalkanes
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A general method has been developed for arylation of readily available 1H-perfluoroalkanes. The method employs aryl iodide and 1H-perfluoroalkane reagents, DMPU solvent, TMP2Zn base, and a copper chloride/phenanthroline catalyst. Preliminary mechanistic studies are reported.
- Popov, Ilya,Lindeman, Sergey,Daugulis, Olafs
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supporting information; experimental part
p. 9286 - 9289
(2011/08/06)
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