- (R)-2- Aryl -4,5-dihydrothiazole -4- carboxylic acid derivative as well as preparation method and application thereof (by machine translation)
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The invention relates to (I - III) aryl - 4444, dihydrothiazoli- 4 4-carboxylic acid derivatives with bactericidal activity as shown in the general formula (R)- 2 - and a preparation method and application, of the pesticide molecular design method, throug
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Paragraph 0032; 0036; 0037
(2020/05/09)
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- Synthesis, biological activities and 3D-QSAR studies of (R)-2-phenyl-4,5-dihydrothiazole-4-carboxamide derivatives containing a sulfur ether moiety
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A series of (R)-2-phenyl-4,5-dihydrothiazole-4-carboxamide derivatives containing a sulfur ether moiety were synthesized and characterized on the basis of NMR and elemental analysis (EA). The crystal structure of (R)-N-(2-methyl-1-(methylthio)propan-2-yl)-2-(4-nitrophenyl)-4,5-dihydrothiazole-4-carboxamide (13d) was determined to show R configuration. The bioasssy results indicated that most title compounds displayed good and broad spectrum antifungal activities against several phytopathogenic fungi. The structure activity relationships were discussed. Based on the antifungal activity of title compounds against Phytophthora capsici, a CoMSIA calculation was performed to establish a 3D-QSAR model, which revealed that electrostatic and hydrophobic fields were the two most significant factors for antifungal activity. According to the established 3D-QSAR model, structure optimization was carried out to find (R)-N-((R)-1-(methylthio)propan-2-yl)-2-(p-tolyl)-4,5-dihydrothiazole-4-carboxamide (15h) with excellent activity against Phytophthora capsici, thus emerging as a new lead compound for novel antiphytopathogenic fungus agent development.
- Liu, Jingbo,Li, Fengyun,Wang, Yuanhong,Zhang, Haoxuan,Dong, Jingyue,Sun, Pengwei,Li, Yuxin,Li, Zhengming
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supporting information
p. 668 - 671
(2018/11/27)
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- Efficient Direct Synthesis of Aziridine-Containing Chiral Tridentate Ligands by the Iminium-Mediated Self-Ring Opening Reaction of Enantiopure Aziridines and Salicylaldehydes
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An efficient method for the direct synthesis of aziridine-containing chiral tridentate ligands was developed from enantiopure aziridines and salicylaldehydes. The method achieved the regiospecific cleavage of more substituted C?N bonds of aziridines through an iminium-mediated self-ring opening reaction of aziridines with up to 95% yield and complete inversion of configuration. The (S)-2-alkylaziridine-derived tridentate ligands displayed excellent activity and stereoselectivity in the zinc trifluoromethanesulfonate-catalyzed asymmetric aldol reactions of acetone and aromatic aldehydes. (Figure presented.).
- Chen, Xingpeng,Lin, Chao,Du, Hongguang,Xu, Jiaxi
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p. 1647 - 1661
(2019/02/27)
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- Convenient Approach to 2-Substituted (Thio)morpholin-3-ones from α-Diazoacetates via X-H Carbene Insertion – Lactamization Sequence
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Stepwise coupling of N-Boc-protected β-aminoethanols or β-mercaptoethylamines with various α-diazoacetates provides a new, unified approach to constructing (thio)morpholin-3-ones. The process involves a Rh2(esp)2-catalyzed X-H insert
- Solovyov, Igor,Dar'in, Dmitry,Krasavin, Mikhail
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p. 7432 - 7438
(2019/11/28)
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- Ti-Catalyzed Radical Alkylation of Secondary and Tertiary Alkyl Chlorides Using Michael Acceptors
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Alkyl chlorides are common functional groups in synthetic organic chemistry. However, the engagement of unactivated alkyl chlorides, especially tertiary alkyl chlorides, in transition-metal-catalyzed C-C bond formation remains challenging. Herein, we describe the development of a TiIII-catalyzed radical addition of 2° and 3° alkyl chlorides to electron-deficient alkenes. Mechanistic data are consistent with inner-sphere activation of the C-Cl bond featuring TiIII-mediated Cl atom abstraction. Evidence suggests that the active TiIII catalyst is generated from the TiIV precursor in a Lewis-acid-assisted electron transfer process.
- Wu, Xiangyu,Hao, Wei,Ye, Ke-Yin,Jiang, Binyang,Pombar, Gisselle,Song, Zhidong,Lin, Song
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supporting information
p. 14836 - 14843
(2018/11/10)
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- Novel anthranilic diamide insecticides: Design, synthesis, and insecticidal evaluation
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Three series of new anthranilic diamide derivatives containing sulfide, N-cyanomethylsulfilimine, and N-cyanomethylsulfoximine groups were designed and synthesized by coupling the active substructures of anthranilic diamides and sulfoxaflor. The structures of the synthesized compounds were confirmed by infrared spectroscopy, 1H and 13C NMR, and elemental analysis. Several unique structural characteristics were revealed via the crystal structure analysis of compound N-(2-(2-methyl-2-(methylthio)propylcarbamoyl)-4-chloro-6-methylphenyl)-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 16e. Bioassay results indicated that most of the synthesized compounds showed superior insecticidal activities against Mythimna separata and Plutella xylostella when compared with the positive control cyantraniliprole. In particular, N-(2-(2-methyl-2-(N-cyanomethylsulfideimino)propylcarbamoyl)-4-chloro-6-methylphenyl)-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 17e showed excellent insecticidal activity against Mythimna separata, with a mortality rate of 100% at a concentration of 1μgmL-1. These results indicated that sulfide, N-cyanomethylsulfilimine, and N-cyanomethylsulfoximine moieties, as important active substructures, could improve or maintain the activity of the anthranilic diamide and promote novel pesticide development.
- Hua, Xuewen,Mao, Wutao,Fan, Zhijin,Ji, Xiaotian,Li, Fengyun,Zong, Guangning,Song, Haibin,Li, Juanjuan,Zhou, Like,Zhou, Lifeng,Liang, Xiaowen,Wang, Genhao,Chen, Xiaoyan
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p. 1491 - 1503
(2014/12/11)
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- Thorpe-Ingold effect in the reaction of vicinal amino primary alcohol hydrogen sulfates and carbon disulfide
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The Thorpe-Ingold effect is a key factor that affects the ring-closure rates and efficiency, as well as the structure of products in some ring-closure reactions. The reaction of vicinal amino primary alcohol hydrogen sulfates and carbon disulfide in the presence of potassium hydroxide produces the desired 4,4-disubstituted thiazolidine-2-thiones, and their isomers 5,5-disubstituted derivatives companying with their oxygen analogues 4,4-disubstituted oxazolidine-2-thiones. The formation of 5,5-disubstituted thiazolidine-2-thiones was rationalized via 2,2-disubstituted aziridine-1-carbodithioate intermediates, which were generated due to the Thorpe-Ingold effect. 4,4-Disubstituted oxazolidine-2-thiones were generated from carbon disulfide and free amino alcohols yielded via basic hydrolysis of active amino alcohol hydrogen sulfates in the reaction system.
- Chen, Ning,Huang, Zhongyan,Zhou, Chan,Xu, Jiaxi
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experimental part
p. 7971 - 7976
(2011/11/14)
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- An improved and mild wenker synthesis of aziridines
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The conventional Wenker synthesis of aziridines from vicinal amino alcohols has been modified by employing mild reaction conditions. Amino alcohols were converted into their hydrogen sulfates with chlorosulfonic acid. The sulfates were cyclized with sodium hydroxide, and even with non-nucleophilic sodium carbonate. The current, improved method extends the scope of the typical Wenker synthesis and is applicable to unstable amino alcohols in hot sulfuric acid and to unstable sulfates which favor elimination and hydroxide displacement in the presence of strong base. Georg Thieme Verlag Stuttgart.
- Li, Xinyao,Chen, Ning,Xu, Jiaxi
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experimental part
p. 3423 - 3428
(2010/11/21)
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- A versatile synthesis of various substituted taurines from vicinal amino alcohols and aziridines
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Taurine and structurally diverse substituted taurines have been synthesized by peroxyformic acid, oxidation of the thiazolidine-2-thione intermediates generated from, vicinal amino alcohols or aziridines and carbon disulfide. The stereochemistry and mechanisms of the reactions are disscussed. The method is a salt-free and versatile route, convenient in terms of purification, and can be used to synthesize optically active substituted taurines.
- Chen, Ning,Jia, Weiyi,Xu, Jiaxi
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experimental part
p. 5841 - 5846
(2010/03/03)
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- Expeditious and practical synthesis of various substituted taurines from amino alcohols
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Various substituted taurines have been synthesized expeditiously and practically in satisfactory to good yields directly from amino alcohols using a two-step, one-pot procedure, in which the amino alcohols undergo sulfuric acid esterification and subsequent sodium sulfite substitution. Treatment of amino-substituted secondary alcohols using the same procedure gave 2-substituted or 1,2-disubstituted taurines, indicating the formation of aziridines as intermediates during the substitution step. This method is one of the most efficient routes for preparing structurally diverse 2-substituted and 1,2- and 2,2-disubstituted taurines. Georg Thieme Verlag Stuttgart.
- Zhang, Wei,Wang, Boyuan,Chen, Ning,Du, Da-Ming,Xu, Jiaxi
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p. 197 - 200
(2008/12/20)
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- PREPARATION OF THIOALKYLAMINES WITH HIGH YIELDS
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The present invention relates to a novel process for the preparation of compounds of the formula (I) by mixing in a first step amino alcohols of the formula (II) with sulfuric acid to yield the salt, by then reacting them in a second step in a drying device to give sulfuric acid esters of the general formula (III) and by reacting these sulfuric acid esters in a third step with mercaptans or salts thereof of the general formula (IV): RSM in each formula, where applicable, R1, R2, R3, R4, R5, R6, R, n and M have the meanings given in the description, in the presence of a diluent and in the presence of a base.
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Page/Page column 6; 21
(2008/06/13)
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- PREPARATION OF THIOALKYLAMINES USING CHLOROSULFONIC ACID
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The present invention relates to a novel process for the preparation of compounds of the formula (I) by reacting in a first step amino alcohols of the formula (II) with chlorosulfonic acid to give sulfuric acid esters of the general formula (III) and by reacting these sulfuric acid esters in a second step with mercaptans or salts thereof of the general formula (IV): RSM in each formula, where applicable, R1, R2, R3, R4, R5, R6, R, n and M have the meanings given in the description, in the presence of a diluent and in the presence of a base.
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Page/Page column 5; 18
(2010/11/26)
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- A new route towards N-(α-methoxybenzyl)aziridines
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A new synthesis of N-(α-methoxyarylmethyl)-2,2-dimethylaziridines is presented. Different benzaldehydes were converted into the corresponding imines upon reaction with 2-bromo-2-methylpropylamine. Treatment of the latter imines with sodium methoxide affor
- D'hooghe, Matthias,Hofkens, Arn,De Kimpe, Norbert
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p. 1137 - 1139
(2007/10/03)
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- Process for production of thioalkylamine derivatives
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The present invention relates to a thioalkylamine derivative represented by general formula (I); and a process for production thereof: wherein each of R1and R2is H, (C1-C4)alkyl, (C3-C8)cyc
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Page/Page column 10-11
(2008/06/13)
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