- A Piperine-Based Scaffold as a Novel Starting Point to Develop Inhibitors against the Potent Molecular Target OfChtI
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The insect chitinase OfChtI from the agricultural pest Ostrinia furnacalis (Asian corn borer) is a promising target for green insecticide design. OfChtI is a critical chitinolytic enzyme for the cuticular chitin degradation at the stage of molting. In thi
- Deng, Ming-Fei,Duan, Hong-Xia,Han, Qing,Li, Hui-Lin,Li, Xiang,Wang, Jin-E,Wu, Nan,Yang, Qing,Zhang, Jing-Yu,Zhu, Kai
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- Preparation method of benzofurocoumarin compound
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The invention discloses a preparation method of a photoactive benzofurocoumarin compound. The photoactive benzofurocoumarin compound is a compound shown as a formula I; the enantioselectivity of the compound shown in the formula I is up to 95-99%. The pho
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Paragraph 0051-0055; 0059-0060; 0153-0155; 0159-0160
(2020/11/23)
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- A facile synthesis of γ-butenolides via cyclization of 3-alkenoic acids with dimethyl sulfoxide and oxalyl bromide
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The combination of dimethyl sulfoxide and oxalyl bromide was used to accomplish the cyclization of 3-alkenoic acids with the aid of a base to afford γ-butenolides, in which bromodimethylsulfonium salt generated in situ was proposed to serve as a Br+ source.
- Ding, Rui,Liu, Yongguo,Liu, Lei,Li, Huimin,Tao, Sichen,Sun, Baoguo,Tian, Hongyu
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supporting information
p. 3001 - 3007
(2019/08/26)
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- Rhodium(ii)-catalysed generation of cycloprop-1-en-1-yl ketones and their rearrangement to 5-aryl-2-siloxyfurans
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Donor-acceptor cyclopropenes formed from enoldiazoketones undergo catalytic rearrangement to 5-aryl-2-siloxyfurans via a novel mechanism that involves a nucleophilic addition of the carbonyl oxygen to the rhodium-activated cyclopropene.
- Marichev, Kostiantyn O.,Wang, Yi,Carranco, Alejandra M.,Garcia, Estevan C.,Yu, Zhi-Xiang,Doyle, Michael P.
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supporting information
p. 9513 - 9516
(2018/08/28)
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- A Novel Method for the Chlorolactonization of Alkenoic Acids Using Diphenyl Sulfoxide/Oxalyl Chloride
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A facile chlorolactonization of alkenoic acids by treatment with diphenyl sulfoxide/oxalyl chloride has been developed. The reaction can generate various chlorolactones in moderate to good yields, wherein the chlorodiphenylsufonium salt derived from diphenyl sulfoxide/oxalyl chloride serves as the source of Cl +.
- Ding, Rui,Lan, Liyuan,Li, Shuhui,Liu, Yongguo,Yang, Shaoxiang,Tian, Hongyu,Sun, Baoguo
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p. 2555 - 2566
(2018/05/03)
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- Palladium-catalyzed C - O hydrogenolysis in γ-hydroxy γ-lactams as an efficient approach to 5-alkyl(aryl)pyrrolidin-2-ones
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5-R-Pyrrolidin-2-ones were synthesized by Pd/Sibunit-catalyzed C - O hydrogenolysis of 5-R-5-hydroxypyrrolidin-2-ones with molecular hydrogen.
- Turova,Berezhnaya,Starodubtseva,Ferapontov,Vinogradov
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p. 859 - 863
(2015/12/24)
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- Diastereo- and enantioselective direct vinylogous Michael addition of γ-substituted butenolides to 2-enoylpyridines catalyzed by chiral bifunctional amine-squaramides
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The diastereo- and enantioselective direct vinylogous Michael addition reaction of γ-substituted butenolides to 2-enoylpyridines has been achieved. A range of γ,γ-disubstituted butenolide derivatives, bearing two consecutive tri- and tetrasubstituted stereogenic centers, were readily obtained in good yields with excellent stereoselectivities (up to >99:1 dr and >99% ee).
- Wang, Zhen-Hua,Wu, Zhi-Jun,Huang, Xue-Qun,Yue, Deng-Feng,You, Yong,Xu, Xiao-Ying,Zhang, Xiao-Mei,Yuan, Wei-Cheng
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supporting information
p. 15835 - 15838
(2015/11/10)
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- Convenient synthesis of α,β-unsaturated γ-butyrolactones and γ-butyrolactams via decarboxylative iodination of paraconic acids and β-carboxyl-γ-butyrolactams using 1,3-diiodo-5,5-dimethylhydantoin
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A convenient synthetic approach to α,β-unsaturated γ-butyrolactones and α,β-unsaturated γ-butyrolactams is developed. The reaction proceeds via decarboxylative iodination of paraconic acids and β-carboxyl-γ-butyrolactams, employing 1,3-diiodo-5,5-dimethylhydantoin (DIH) under irradiation, followed by dehydroiodination of β-iodo-γ-butyrolactones and γ-butyrolactams providing good yields of α,β-unsaturated γ-butyrolactones and γ-butyrolactams, which are synthetically useful building blocks in organic synthesis.
- Phae-Nok, Supasorn,Kuhakarn, Chutima,Pohmakotr, Manat,Reutrakul, Vichai,Soorukram, Darunee
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p. 11087 - 11095
(2015/11/25)
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- Electrochemical generation and catalytic use of selenium electrophiles
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The generation and use of selenium electrophiles in catalytic, electrochemically driven selenenylation-elimination sequences is described. Georg Thieme Verlag Stuttgart.
- Niyomura, Osamu,Cox, Matthew,Wirth, Thomas
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p. 251 - 254
(2007/10/03)
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- Facile synthesis of 2-arylpyrroles from 4-oxo-butanoic acids and their use in the preparation of bis(pyrrolyl)methanes
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A range of 3-aroyl-propionic acids have been cyclised to unsaturated lactones which, upon reduction using DIBAL-H and reaction with an ammonia source, gave 2-arylpyrroles (Ar = Ph, 1-naphthyl, o-phenoxyphenyl and 4-methyl-2-methylsulfanylphenyl) in excellent yields. Reaction of 2,6-disubstituted aroylpropanals (Ar = 2,4,6-Me3C6H2, anthracenyl and 2-Me-naphthalen-1-yl) with an ammonia source failed to generate pyrroles. The arylpyrroles react readily with ketones or aldehydes in ethanol or under eutectic mix melt conditions to give bis-(pyrrolyl)methanes in excellent isolated yields.
- Jones, David J.,Gibson, Vernon C.
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p. 1121 - 1138
(2007/10/03)
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- Rearrangement of 5-benzoyl-3(2H)-isothiazol-3-ones to 6-benzoyl 2,3-dihydro-1,3-thiazin-4(2H)-ones
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5-Benzoyl-3(2H)-isothiazol-3-ones 4 were converted to the corresponding isomeric 6-benzoyl-2-substituted-2,3-dihydro-1,3-thiazin-4(2H)-ones 13 by the following reaction sequence: the preparation of aroylpropionamides (3), the conversion of (3) to aroyliso
- Tsolomiti, Georgia,Tsolomiti, Kyriaki,Tsolomitis, Athanase
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p. 247 - 252
(2007/10/03)
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- Studies with pyrazol-3-carboxylic acid hydrazide: The synthesis of new pyrazolyloxadiazole and pyrazolyltriazole derivatives
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A simple and versatile method for the synthesis of pyrazol-3-yl-1,3,4- oxadiazole, pyrazol-3-yl-1,2,4-triazole, (1,5-diphenylpyrazol-3-yl)-(3,5- dimethyl-1-carbonyl)pyrazole, and (1,5-diphenylpyrazol-3-yl)-(5-hydroxy-3- metheyl-1-carbonyl)pyrazole derivat
- Elkholy, Yehya,Ali, Korany,Farag, Ahmad
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p. 2037 - 2049
(2007/10/03)
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- Convenient synthesis of some new substituted pyrazolyl-1,3,4-oxadiazoles and pyrazolyl-1,2,4-triazoles
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A simple and versatile method for the synthesis of pyrazol-3-yl-1,3,4- oxadiazole, pyrazol-3-yl-1,2,4-triazole, (1,5-diphenylpyrazol-3-yl)-(3,5- dimethyl-1-carbonyl)pyrazole and (1,5-diphenylpyrazol-3-yl)-(5-hydroxy-3- metheyl-1-carbonyl)pyrazole derivati
- Elkholy, Yehya M.,Ali, Korany A.,Farag, Ahmad M.
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p. 1183 - 1188
(2007/10/03)
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- Phenylpropionic acid derivatives
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Specified phenylpropionic acid derivatives and analogues thereof have an antagonistic activity to α 4 integrin. They are used as therapeutic agents or preventive agents for various diseases concerning α 4 integrin, such as inflammatory diseases in which α
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- Enantiodivergent syntheses of γ-substituted butenolides with tertiary and quaternary asymmetric centers
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Continuous nucleophilic addition with several organometallic reagents to tricyclic lactone (-)-1 proceeded diastereoselectively. Newly generated tertiary and quaternary asymmetric centers were controlled by the order in which the nucleophilic reagents were added. Using this methodology, enantiodivergent syntheses of several γ-substituted butenolides with tertiary and quaternary asymmetric centers were established from a single chiral material.
- Suzuki, Katsufumi,Inomata, Kohei
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p. 745 - 749
(2007/10/03)
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- Preparation of β-substituted γ-keto esters by the grignard reaction on N-acylpyrazoles
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Various γ-keto esters were prepared by either the alcoholysis of N-(4-oxoalkanoyl)pyrazoles or the Grignard replacement of pyrazole moiety of 4-(N-pyrazolyl)-4-oxoalkanoic esters. By using 3-phenyl-ι-menthopyrazole as a chiral auxiliary, β-substituted γ-keto esters were enantioselectively obtained.
- Kashima, Choji,Shirahata, Yoshie,Tsukamoto, Yoshihiro
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p. 309 - 317
(2007/10/03)
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- Palladium-catalyzed regioselective arylation of silyloxy compounds with triarylantimony diacetates
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The regioselective arylation of silyloxy compounds with triarylantimony diacetates was performed by using palladium catalysts. The silyl enol ether, silyl dienol ethers and silyl oxycyclopropane were arylated in the presence of a palladium catalysts with triarylantimony(V) diacetates under mild conditions. The results showed that the given method had the advantage of mild conditions which involved the use of PdCl2 at room temperature even in the presence of water.
- Kang, Suk-Ku,Ryu, Hyung-Chul,Honge, Young-Taek
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p. 3350 - 3351
(2007/10/03)
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- Palladium-catalyzed coupling and carbonylative coupling of silyloxy compounds with hypervalent iodonium salts
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Arylation and alkenylation of 1-ethoxy-1-trimetylsilyloxycyclopropane with diphenyliodonium tetrafluoroborate and alkenyliodonium tetrafluoroborate were accomplished by slow addition of silyloxycyclopropane to iodonium salts in the presence of Pd(OAc)2 (2 mol %) and DME/H2O (4 : 1) to afford β-substituted ester. Alternatively, carbonylative coupling of silyloxypropane was carried our by slow addition of silyloxypropanes to iodonium salts under CO(1 atm) at room temperature in aqueous medium. The palladium-catalyzed coupling of ketene trimethylsilyl acetals with iodonium sails is also described.
- Kang, Suk-Ku,Yamaguchi, Tokutaro,Ho, Pil-Su,Kim, Won-Yeob,Yoon, Seok-Keun
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p. 1947 - 1950
(2007/10/03)
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- Photodecomposition of pyrazolone and furanone dyes in polymer matrices
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Synthesis of monoazo dyes based on 2-phenyl-5-furanone was developed. Spectral properties of dyes based on aniline, xylidine, p-nitroaniline, p-chloroaniline, and anthranilic acid were studied. Photodecomposition of these dyes in polystyrene, polymethyl m
- Kovzhina,Sokolova,Dmitrieva,Pesenko
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p. 428 - 433
(2007/10/03)
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- PREPARATION AND REACTIVITY OF FUNCIONALIZED ALKENYL-ZINC, -COPPER, AND -CHROMIUM ORGANOMETALLICS
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β-Halogeno-α,β-unsaturated carbonyl derivatives were converted to the corresponding zinc organometallics 2a under mild conditions in THF (Zn dust, 25-45 deg C, 1-4h).These funcionalized alkenylzinc iodides react with a variety of alkenyl and aromatic iodides affording the desired coupling products in 40-97percent yield.The addition of a THF solution of CuCN*2LiCl to 2a affords the corresponding organocopper derivatives 2b which rect with electophiles, such as alkynyl and allylic halides, nitro olefins, enones, and chlorotrimethylstannane providing polyfuncional unsaturated carbonyl compounds in 71-95percent yield.The insertion of chromium (II) chloride to β-iodo and to some β-(p-tosyl)enones in DMF furnishes new funcionalized chromium (III) organometallics 2c which react with aldehydes providing γ-hydroxy unsaturated carbonyl derivatives in 40-91percent yield.The synthetic scope and the limitations of this methodology are discussed. Key words: funcionalized organozinc halides, alkenylchromium(III) compounds, copper-zinc organometallics.
- Knochel, Paul,Rao, C. Janakiram
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- MELDRUM'S ACID - A REAGENT FOR THE SYNTHESIS OF UNSATURATED γ-LACTONES AND β-ACYLACRYLIC ACIDS
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The thermal cyclization of 2,2-dimethyl-5-(2-aryl-2-oxoethyl)-1,3-dioxan-4,6-diones forms 5-aryl-β,γ-butenolides.Regioselective chlorination of 2,2-dimethyl-5--1,3-dioxane-4,6-diones by SO2Cl2 gives the 5-chloro derivatives, thes
- Zav'yalov, S. I.,Zavozin, A. G.,Kravchenko, N. E.
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p. 1090 - 1092
(2007/10/02)
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- METHYL 3-PHENYLSULPHONYL ORTHOPROPIONATE: AN EFFICIENT REAGENT FOR THE SYNTHESIS OF γ-LACTONES AND BUTENOLIDES
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Treatment of methyl 3-phenylsulphonyl orthopropionate with n-BuLi gives the corresponding carbanion which reacts with aldehydes or ketones to yield β-phenylsulphonyl-γ-lactones.Base-catalysed elimination yields α,β or β,γ-butenolides.
- Carretero, Juan Carlos,Lombaert, Stephane De,Ghosez, Leon
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p. 2135 - 2138
(2007/10/02)
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- THE CONVERSION OF FURANS TO 2(3H)-BUTENOLIDES
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2-Aryl- and 2-alkylfurans are converted into the corresponding 5-organyl-2(3H)-butenolides by the oxidation of boron derivatives with m-chloroperbenzoic acid.
- Pelter, Andrew,Rowlands, Martin
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p. 1203 - 1206
(2007/10/02)
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- 145. Analytic and Preparative Resolution on Racemic γ- and δ-Lactones by Chromatography on Cellulose Triacetate. Relationship between Elution Order and Absolute Configuration
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Enantiomers of various chiral five- and six-membered-ring lactones, which are important classes of cpmpounds (flavour and pheromone components, key intermediates in the synthesis of biologically active substrates) have been separated chromatographically on the chiral phase cellulose triacetate, crystallographic form I (CTA I).Four different series of five-membered-ring lactones, relationships have been found between the elution order of the enantiomers and their absolute configuration.Preparative resolutions of γ-phenyl-γ-butyrolactone (1) and of the pheromone component 5b have been carried out to demonstrate the applicability of the method to g-scale separations.
- Francotte, Eric,Lohmann, Dieter
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p. 1569 - 1582
(2007/10/02)
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- FRIEDEL-CRAFTS ALKYLATIONS OF FERROCENE WITH UNSATURATED LACTONES, SOME UNUSUAL REACTIONS CAUSED BY THE Β-FERROCENYLCARBENIUM ION
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Friedel-Crafts alkylations of ferrocene with 5- and 6-membered unsaturated lactones have been studied.The expected alkylation products were isolated in the case of 5-membered lactones, while several products such as unsaturated ferrocenyllactones, ferrocenyldiketones as well as ferrocenylhydroxylactones were isolated in the case of 6-membered lactones. β-Ferrocenylcarbenium ion was suggested to be the key intermediate in this case.
- Salisova, M.,Toma, S.,Solcaniova, E.
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- PALLADIUM(II) CATALYZED CYCLIZATION OF ALKYNOIC ACIDS
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Under the catalytic action of palladium(II) in the presence of triethylamine, 3-, 4-, and 5-alkynoic acids afford 3-buten-4-olides, 4-penten-4-olides,and 5-hexen-5-olide, respectively, in good to excellent yields.
- Lambert, Claude,Utimoto, Kiitiro,Nozaki, Hitosi
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p. 5323 - 5326
(2007/10/02)
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- Some Observations Concerning the Lactonization of 3-Aroylpropionic Acids
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The ease of lactonization og the γ-keto acids ArCOCH2CH2COOH is shown to depend on the nature of the aryl group: the presence of electron-releasing substituents on the aryl group results in a more rapid reaction as compared to the presence of electron-wit
- Tsolomitis, A.,Sandris, C.
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p. 1545 - 1548
(2007/10/02)
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- Reactions of some Δβ,γ-Butenolides Having no Exocyclic Double bonds
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Ring-opening of γ-aryl-Δβ,γ-butenolides (I) takes place in a different manner compared to those having an exocyclic double bond at the α-position.I react with hydrazine hydrate in cold or boiling ethanol to give 6-aryl-4,5-dihydropyridazine-3(2
- Hashem, A. I.,Shaban, M. E.,El-Kafrawy, A. F.
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p. 763 - 764
(2007/10/02)
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- Improved Synthesis of 3-Aralkylidine-5-arylthiophen-2-(3H)ones
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3-Aralkylidene-5-arylthiophen-2-(3H)ones can be prepared in two steps from 4-aryl-4-oxobutanoic acids through the intermediacy of butenolides and thiophenones generated by the sequential action of acetic anhydride, sodium hydrosulfide and aromatic aldehyd
- Miller, Gerald A.,Heindel, Ned D.,Minatelli, John A.
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p. 1253 - 1254
(2007/10/02)
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- PHOTOCHEMISTRY OF 5-ARYL-2(3H)-FURANONES. A NEW ROUTE TO THE SYNTHESIS OF CHROMONES
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The photochemistry of 5-phenyl-, 5-(2',5'-dimethoxyphenyl)-, 5-(2'-acetoxy-5'-methoxyphenyl)- and 5-(2',5'-diacetoxyphenyl)-2(3H)-furanone (1a-d) has been investigated.Compound 1a yields pheny vinyl ketone as expected.Similarly, 1b affords the corresponding aryl vinyl ketone but, in this case, photodimerization also occurs.Irradiation of the two o-acetoxyaryl furanones 1c and 1d gives rise to the formation of chromones as the main products.This interesting result can be accounted for in terms of a photochemical opening of the lactonic ring followed by radical addition to the acetoxy group.
- Martinez-Utrilla, R.,Miranda, M. A.
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p. 2111 - 2114
(2007/10/02)
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- SYNTHESE DE Δ-2 BUTENOLIDES A PARTIR DU FURFURAL
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The reaction of two molecular equivalents of organolithium derivatives with 4-hydroxy-2-butenolide (easily prepared from furfural) leads to 4-substituted butenolides with excellent yields.
- Machado-Araujo, F.Welbaneide,Gore, Jacques
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p. 1969 - 1972
(2007/10/02)
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