- Alpha-amino acid derivative containing piperidine thiazole heterocycle and preparation method and application of alpha-amino acid derivative
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The invention discloses an alpha-amino acid derivative containing piperidine thiazole heterocycle. The alpha-amino acid derivative has a structural formula of formula I shown in the description, wherein in formula I, Ar is a phenyl group or a substituted phenyl group, a substituted group of the substituted phenyl group is one of a trifluoromethyl group, fluorine, chlorine or bromine, and R is oneof H and isopropyl. The invention further discloses a preparation method of the alpha-amino acid derivative and application of the alpha-amino acid derivative serving as an insecticide to prevention and control of armyworms. The novel alpha-amino acid derivative containing the piperidine thiazole heterocycle is simple in preparation method, can be used for prevention and control of armyworm insectpests, particularly has a good insecticidal activity against the armyworms, and provides bases for research and development of amino acid pesticides.
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Paragraph 0019
(2019/02/27)
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- A Simple and Efficient Method for the Preparation of α-Halogenated Ketones Using Iron(III) Chloride and Iron(III) Bromide as Halogen Sources with Phenyliodonium Diacetate as Oxidant
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α-Halogenated ketones are both unique structure moieties existing in biologically natural products and valuable synthetic intermediates for the preparation of functional molecules. An efficient and scalable method for the preparation of α-halogenated ketone using iron (III) chloride and iron (III) bromide as halogen sources with phenyliodonium diacetate as oxidant has been developed, featuring mild reaction conditions, environmentally friendly reagents, and wide substrate scope. Notably, the three-step synthesis of drug prasugrel was achieved using this developed method as a key step with 30% yield on gram-scale. Additionally, the reaction mechanism involving chloride cation was proposed based on some preliminary control experiments. (Figure presented.).
- Tang, Shi-Zhong,Zhao, Wenshuang,Chen, Tao,Liu, Yang,Zhang, Xiao-Ming,Zhang, Fu-Min
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supporting information
p. 4177 - 4183
(2017/12/18)
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- Peptidyl cyclopropenones: Reversible inhibitors, irreversible inhibitors, or substrates of cysteine proteases?
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Peptidyl cyclopropenones were previously introduced as selective cysteine protease reversible inhibitors. In the present study we synthesized one such peptidyl cyclopropenone and investigated its interaction with papain, a prototype cysteine protease. A set of kinetics, biochemical, HPLC, MS, and 13C-NMR experiments revealed that the peptidyl cyclopropenone was an irreversible inhibitor of the enzyme, alkylating the catalytic cysteine. In parallel, this cyclopropenone also behaved as an alternative substrate of the enzyme, providing a product that was tentatively suggested to be either a spiroepoxy cyclopropanone or a gamma-lactone. Thus, a single family of compounds exhibits an unusual variety of activities, being reversible inhibitors, irreversible inhibitors and alternative substrates towards enzymes of the same family.
- Cohen, Meital,Bretler, Uriel,Albeck, Amnon
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p. 788 - 799
(2013/09/02)
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- Pyridines from azabicyclo[3.2.0]hept-2-en-4-ones through a proposed azacyclopentadienone
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Pyridines have been formed by heating azabicyclo[3.2.0]hept-2-en-4-ones in toluene. The generation of a 3-azacyclopentadienone intermediate via a [2 + 2]-cycloreversion is proposed as the key step. A Diels-Alder reaction of a styrene, extrusion of carbon monoxide, and loss of hydrogen then gives the pyridine. The process parallels the well-known synthesis of benzenes from cyclopentadienones. The azabicyclo[3.2.0]hept-2-en-4-ones were synthesized from the reaction between readily available cyclopropenones and 1-azetines, in which the cyclopropenones behave as all-carbon 1,3-dipolar equivalents.
- Hemming, Karl,Khan, Musharraf N.,Kondakal, Vishnu V. R.,Pitard, Arnaud,Qamar, M. Ilyas,Rice, Craig R.
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supporting information; experimental part
p. 126 - 129
(2012/02/16)
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- PIPERAZINYL DERIVATIVES USEFUL AS MODULATORS OF THE NEUROPEPTIDE Y2 RECEPTOR
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The present invention is directed to piperidinyl and piperazinyl derivatives of formula (II) useful as inhibitors of the NPY Y2 receptor, pharmaceutical compositions comprising said compounds, processes for the preparation of said compounds and the use of said compounds for the treatment and / or prevention of disorders, diseases and conditions mediated by the NPY Y2 receptor.
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Page/Page column 138
(2009/07/18)
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- Synthesis of chiral cis-1,2,3-trisubstituted aziridines
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Chiral cis-1,2,3-trisubstituted aziridines were conveniently synthesized from (1R,2S)-(-)- or (1S,2R)-(+)-norephedrine via the corresponding chiral N-(arylidene)-β-chloroamines. The enantiomeric purity of the chiral aziridines (e.e. >98%) was established by NMR spectroscopy utilizing (S)-(+)-1-(9-anthryl)-2,2,2-trifluoroethanol. (C) 2000 Elsevier Science Ltd.
- Van, Tuyen Nguyen,De Kimpe, Norbert
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p. 7299 - 7304
(2007/10/03)
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- Reactions of alkyl methyl ketoximes with tetrasulfur tetranitride antimony pentachloride complex (S4N42.SbCl5): A regioselective formation of 3-alkyl-4-methyl-1,2,5-thiadiazoles and their mechanism of formation
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Treatment of alkyl methyl ketoximes with tetrasulfur tetranitride antimony pentachloride complex (S4N4·SbCl5) in aromatic solvents such as benzene and toluene at 60 °C led to the regioselective formation of 3-alkyl- 4-methyl-1,2,5-thiadiazoles in low yields, whereas the reactions of alkyl aryl ketoximes under the same conditions gave exclusively N-arylalkanamides in good yields. A mechanism is proposed for the formation of 3-alkyl-4- methyl-1,2,5-thiadiazoles.
- Kim, Kil Joong,Kim, Kyongtae
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p. 147 - 157
(2007/10/03)
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- Indium(III) chloride-promoted rearrangement of epoxides: A selective synthesis of substituted benzylic aldehydes and ketones
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A simple and efficient procedure for the rearrangement of substituted epoxides catalyzed by InCl3 has been developed. Aryl-substituted epoxides isomerize with complete regioselectivity to form a single carbonyl compound via cleavage of the benzylic C-O bond. The reactions are simple, fast, and high yielding. This procedure is very mild compared to those catalyzed with BF3 and other Lewis acids and compatible with several acid-sensitive functionalities. This protocol provides a highly selective synthesis of substituted benzylic aldehydes and ketones. However, rearrangement of alkyl- substituted epoxides is not very selective.
- Ranu, Brindaban C.,Jana, Umasish
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p. 8212 - 8216
(2007/10/03)
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- Chemoenzymatic synthesis of chiral epoxides. Preparation of 4-phenyl-2,3- epoxybutane and 1-phenyl-1,2-epoxypropane
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All the stereoisomers of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2- epoxypropane (β-methylstyrene oxide) have been prepared in three steps from 4-phenyl-2-butanone and 1-phenyl-2-propanone or 1-phenyl-1-propanone respectively. The key step is the microbiological reduction of the corresponding haloketones. These results confirm those previously described and demonstrate that the chemoenzymatic synthesis of homochiral 2,3-epoxides is a general method that can be used whatever the starting ketone.
- Besse,Renard,Veschambre
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p. 1249 - 1268
(2007/10/02)
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- C-Nitroso compunds. Part XXXVII. The reactivity of α-chloronitroso compounds towards organoaluminium reagents
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With sterically unhindered and certain moderately hindered α-chloronitroso compounds 1 trimethylaluminium at low temperature gives, via complexes 2 and 3, the methyl nitrones 4 (Scheme 1).Several intermediate complexes 3 lose methane upon heating and rearrange to α-chloroimines 5 (Scheme 2), the structure of which is determined by that of the precursors (E- or Z-geometry; cf.Scheme 6).More sterically hindered α-chloronitroso compounds containing quaternary carbon undergo C-C rupture when treated with trimethylaluminium, thus forming hydroxamic acid chlorides, formally HCl adducts of nitrile oxides (cf. 8j in Scheme 3; 8k in Scheme 4).In the latter case, subsequent reactions lead to overall ring enlargement, i. e. formation of the seven-membered cyclic oxime 12.With triethylaluminium and triisobutylaluminium, α-chloronitroso compounds are mainly reduced to oximes and the isomeric amides (Scheme 7).
- Lub, J.,Beekes, M. L.,Boer, Th. J. de
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- ELECTROSYNTHESIS OF KETONES FROM ORGANIC HALIDES AND ANHYDRIDES
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The electroreduction of benzylic and allylic halides in the presence of anhydrides affords ketones in moderate to good yields.The electrolysis is performed in an undivided cell, under constant current, using an aluminium or magnesium anode.
- d'Incan, Esther,Sibille, Soline,Perichon, Jacques,Moingeon, Marie-Odile,Chaussard, Jacques
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p. 4175 - 4176
(2007/10/02)
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- ON THE MECHANISM OF THE REARRANGEMENT OF N-ARYL α,α-DICHLOROKETIMINES WITH LITHIUM ALUMINIUM HYDRIDE
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Experimental evidence is provided that the rearrangement of N-aryl α,α-dichloroketimines with lithium aluminium hydride in ether, observed as a competitive reaction during the stereospecific synthesis of cis aziridines, proceeds via consecutive transforma
- Kimpe, Norbert De,Verhe, Roland,Buyck, Laurent De,Schamp, Niceas
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p. 233 - 240
(2007/10/02)
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- Halogen Epoxides, 3. Reactions of 2-Chloro- and 2,3-Dichlorooxiranes with Silver Tetrafluoroborate: Synthesis of α-Fluorinated Carbonyl Compounds
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Reactions of chlorinated oxiranes with silver tetrafluoroborate in ether have been investigated.Substituted-2-chlorooxiranes (4a - e) afforded the corresponding α-fluorocarbonyl compounds (7a - e) as major products and the isomeric α-chlorocarbonyl compounds (8a - e) as minor products.Substituted 2,3-dichlorooxiranes (10, 14, 20, 24) yielded the isomeric α,α-dichloroketones (13, 19, 22, 26b, 29b) as well as the corresponding α-chloro-α-fluoroketones (12, 17, 21, 26a, 29a) and α,β-unsaturated α-chloroketones (18, 23, 27, 30).The course of the reaction was rationalized.Similar reaction with α-chloroketones and with α,α-dichloroketones succeeded only at substrates (8b, 35) in which the chlorine substituents were in benzylic positions.
- Griesbaum, Karl,Keul, Helmut,Kibar, Riza,Pfeffer, Bernd,Spraul, Manfred
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p. 1858 - 1870
(2007/10/02)
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