- Access to pyrrolo[2,1-: A] isoindolediones from oxime acetates and ninhydrin via Cu(i)-mediated domino annulations
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A copper-mediated domino condensation reaction of readily accessible oxime acetates with ninhydrin is reported to afford pyrrolo[2,1-a]isoindolediones via new C-C & C-N bond formations. A wide range of oxime acetates were shown to generally participate in the reaction to produce the condensed products in excellent yields. The necessary control experiments were performed and the mechanism is proposed to involve sequentially the formation of iminium radical via Cu-mediated N-O bond cleavage of oxime acetates, addition of the radical to ninhydrin and rearrangement via ring expansion.
- Upare, Atul,Chouhan, Neeraj Kumar,Ramaraju, Andhavaram,Sridhar, Balasubramanian,Bathula, Surendar Reddy
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supporting information
p. 1743 - 1746
(2020/03/17)
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- Direct Enamido C(sp2)?H Diphosphorylation Enabled by a PCET-Triggered Double Radical Relay: Access to gem-Bisphosphonates
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Herein we report a novel and straightforward protocol for the construction of valuable gem-BPs by means of proton-coupled electron-transfer (PCET)-triggered enamido C(sp2)?H diphosphorylation. This reaction represents a rare example of realizing the challenging double C?P bond formation at a single carbon atom, thus providing facile access to a broad variety of structurally diverse bisphosphonates from simple enamides under silver-mediated conditions. Initial mechanistic studies demonstrated that the diphosphorylation involves two rounds of PCET-initiated radical relay process.
- Cao, Hao-Qiang,Liu, Hao-Nan,Liu, Zhe-Yuan,Ma, Jun-An,Qiao, Bao-Kun,Zhang, Fa-Guang
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supporting information
p. 5515 - 5521
(2020/04/27)
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- Preparation method of pyrimidine salicylate oxime ester compound and application of compound as herbicide
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The invention discloses a preparation method of a pyrimidine salicylate oxime ester compound and application of the compound as a herbicide, belongs to the technical field of herbicides, and relates to the application of the herbicide in selectively controlling gramineous weeds and broadleaf weeds for crops. The compound is a pyrithiobac oxime ester compound. The preparation method includes the following steps that acids of pyrithiobac are condensed with substituted acetophenoxime in the presence of an organic solvent and a condensation agent to prepare a (I) compound. At 45 g a.i./hm, thecompound can effectively control echinochloa crusgalli, eleusineindica, setaria viridis, amaranthus retroflexus, portulaca oleracea, chenopodium album and other grassy weeds and broadleaf weeds, can serve as a candidate herbicide in a cotton field and has potential industrial application. Meanwhile, the compound is environmentally friendly, low in toxicity and highly safe for crops such as cotton.The invention provides a preparation technology of the efficient and safe novel pyrimidine salicylate oxime ester compound with the herbicidal activity, the compound can be massively produced, the yield is high and the purity is high.
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Paragraph 0081; 0082
(2019/10/22)
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- Copper-Catalyzed Three-Component Domino Cyclization for the Synthesis of 4-Aryl-5-(arythio)-2-(trifluoromethyl)oxazoles
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A copper-catalyzed oxidative cyclization of oxime, arylthiol, and trifluoroacetic anhydride for the construction of trisubstituted oxazoles has been developed. This transformation combines N-O bond cleavage, C-H functionalization, and intramolecular annulation, providing a practical protocol for the introduction of a trifluoromethyl (-CF3) group at oxazole rings.
- Xiao, Fuhong,Yuan, Shanshan,Huang, Huawen,Zhang, Feng,Deng, Guo-Jun
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supporting information
p. 8533 - 8536
(2019/10/17)
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- Trifloxystrobin and preparation method of intermittent thereof
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The invention relates to a preparation method of trifloxystrobin. Preparation reaction of the trifloxystrobin is as shown in the description, wherein R is selected from C2-C5 linear alkyl or C3-C5 branched alkyl; in bromination reaction, a brominating agent is selected from NBS or 1,3-dibromo-5,5-dimethylhydantoin.
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Paragraph 0094-0097
(2018/12/13)
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- Rh(III)- and Zn(II)-Catalyzed Synthesis of Quinazoline N-Oxides via C-H Amidation-Cyclization of Oximes
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Quinazoline N-oxides have been prepared from simple ketoximes and 1,4,2-dioxazol-5-ones via Rh(III)-catalyzed C-H activation-amidation of the ketoximes and subsequent Zn(II)-catalyzed cyclization. The substrate scope and functional group compatibility were examined. The reaction features relay catalysis by Rh(III) and Zn(II).
- Wang, Qiang,Wang, Fen,Yang, Xifa,Zhou, Xukai,Li, Xingwei
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supporting information
p. 6144 - 6147
(2016/12/09)
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- IMPROVED METHOD FOR PRODUCING SPECIFIC OXIMES AND OXIMETHERS
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Method for preparing certain oximes and oxime O-methyl ethers by reacting poorly water-soluble carbonyl compounds with salts of hydroxylamine or hydroxylamine O-methyl ether or the free base of hydroxylamine in the presence of certain phosphoric esters or salts thereof of the formula (I) wherein R1, R2 and X are defined as specified in the description.
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Paragraph 0070; 0077-0080
(2016/05/11)
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- TETRAZOLINONE COMPOUND AND USE THEREOF
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The compound represented by formula (1): wherein R4 and R5 each represents a hydrogen atom, a halogen atom, or a C1-C3 alkyl group; R6 represents a C1-C4 alkyl group, a C3-C6 cycloalkyl group, or the like; R7, R8, and R9 each represents a hydrogen atom, a halogen atom, or the like; R10 represents a C1-C3 alkyl group, or the like; R13 represents a C1-C3 alkyl group, or the like; and Q represents a phenyl group, or the like; has an excellent control effect on pests.
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Paragraph 0844-0845
(2015/11/16)
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- AN IMPROVED PROCESS FOR THE SYNTHESIS OF STROBILURIN FUNGICIDES VIZ TRIFLOXYSTROBIN AND KRESOXIM-METHYL
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The present invention relates to an improved process for the synthesis of E-isomer of compound of formula (5). It further relates to the conversion of formula (5), wherein R is H, to Intermediate (I) and subsequently to substantially pure Trifloxystrobin, compound of formula (I) in good yield.
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Page/Page column 29; 33
(2013/10/21)
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- O-acetyl oximes as transformable directing groups for Pd-catalyzed C-H bond functionalization
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[Chemical equation presented] O-Acetyl oxlmes serve as effective directing groups for Pd-catalyzed sp2 and sp3 C-H functionalization reactions. The C-H functionalization products can be subsequently transformed Into ortho- or β-functionalized ketones, alcohols, amines, and heterocycles.
- Neufeldt, Sharon R.,Sanford, Melanie S.
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supporting information; experimental part
p. 532 - 535
(2010/05/02)
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- Quinone-sensitized steady-state photolysis of acetophenone oximes under aerobic conditions: Kinetics and product studies
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Oxidation of oximes via photosensitized electron transfer (PET) results in the formation of the corresponding ketones as the major product via oxime radical cations and iminoxyl radicals. The influence of electron-releasing and electron-accepting substituents on these reactions was studied. The observed substituent effect strongly supports formation of iminoxyl radicals from the oximes via an electron transfer-proton transfer sequence rather than direct hydrogen atom abstraction. Correlation of the relative conversion of the oximes with Hammett parameters shows that radical effects dominate for the meta-substituted acetophenone oximes (ρrad/ ρpol = 5.4; r2 = 0.93), whereas the para-substituted oximes are influenced almost equally by radical and ionic effects (ρrad/ ρpol = -1.1; r2 = 0.98). From these data sets we conclude that the follow-up reactions proceed through a number of intermediates with both radical and ionic character. This was confirmed by product studies with the use of an isotopically labeled nucleophile. In addition to the major oxidation product (ketone), a chlorine-containing product was often identified as well. Studies on the formation of this product show that the most likely pathway is either via a direct nucleophilic addition in a complex formed between the oxime radical cation and the chloranil radical anion or via a radical substitution (SH2) mechanism. These studies show that with the increasing use of oximes as drugs and pesticides, intake of these chemicals followed by enzymatic oxidation may result in the formation of a variety of reactive intermediates, which may lead to cell and tissue damage.
- Park, Adriana,Kosareff, Nicole M.,Kim, Jason S.,De Lijser, H. J. Peter
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p. 110 - 118
(2008/02/12)
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- Synthesis and properties of axially-chiral N-(2,6-disubstituted)phenyl triazolones
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Certain ortho-substituted phenyl triazolone compounds are fungicidal. When two ortho-substituents are present, stable atropisomers can be isolated. Several methods for resolving racemic intermediates into the enantiomers are described, including separations of diasteromeric ester derivatives and diasteromeric salts. The intermediates were converted into products in which the absolute configuration can be correlated to biological activity.
- Brown, Richard J.,Annis, Gary,Casalnuovo, Albert,Chan, Dominic,Shapiro, Rafael,Marshall, William J.
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p. 4361 - 4375
(2007/10/03)
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- Practical Asymmetric Synthesis of (S)-MA20565, a Wide-Spectrum Agricultural Fungicide
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A practical asymmetric synthesis of a wide-spectrum agricultural fungicide, (S)-MA20565 (1), is described. The convergent synthesis was achieved starting from commercially available 3-(trifluoromethyl)aniline (7) in 44% overall yield through five steps and 2-bromobenzaldehyde (9) in 48% overall yield through four steps, respectively. (S)-O-[1-(3-Trifluoromethylphenyl)ethyl]hydroxylamine (2), a key intermediate of 1, was prepared via ruthenium(II)-catalyzed asymmetric transfer hydrogenation of 1-(3-trifluoromethylphenyl)ethanone (6) followed by chlorination using methanesulfonyl chloride and oxyamination using potassium acetohydroxamate with high level of stereocontrol.
- Tanaka, Ken,Katsurada, Manabu,Ohno, Fumihiko,Shiga, Yasushi,Oda, Masatsugu,Miyagi, Miwa,Takehara, Jun,Okano, Kazuya
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p. 432 - 437
(2007/10/03)
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- Process for the preparation of o-chloromethyl-phenylglyoxylic acid derivatives
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There is described a process for the preparation of a compound of formula I STR1 in which process: a) a compound of formula II STR2 is reacted with an organolithium compound of formula III b) the resulting lithium complex is reacted with a compound of for
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- N-phenylcarbamate compound, process for preparing the sasme and biocidal composition for control of harmful organisms
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A novel N-phenylcarbamate compound or its salt where possible, which is useful as the active ingredient of a biocidal composition for control of harmful organisms, is represented by the following general formula (I): STR1 wherein R1 is unsubsti
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- Isoxazolyl benzamides as pharmacological agents
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Substituted or unsubstituted isoxazolyl benzamides, e.g., o-(3-phenylisoxazol-5-yl)-N-methylbenzamide, are prepared by cyclizing a corresponding 1-hydroxy-1-[substituted or unsubstituted-β-(hydroxyimino)phenethyl]-2-alkyl phthalimidine with a strong acid and are useful as minor tranquilizers, muscle relaxants, and sleep inducers.
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