- Synthesis and biological activity of 2′, 3′-iso-aryl-abscisic acid analogs
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2′, 3′-iso-Benzoabscisic acid (iso-PhABA), an excellent selective abscisic acid (ABA) analog, was developed in our previous work. In order to find its more structure-activity information, some structural modifications were completed in this paper, includi
- Wan, Chuan,Wang, Mingan,Yang, Dongyan,Han, Xiaoqiang,Che, Chuanliang,Ding, Shanshan,Xiao, Yumei,Qin, Zhaohai
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- An expedient synthesis of highly functionalized 1,3-dienes by employing cyclopropenes asC4units
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An efficient method has been described to synthesize dicarbonyl functionalized 1,3-dienes by cleaving the CC bond of enaminones with cyclopropenes in the presence of a rhodium catalyst. The acetate-substituted cyclopropenes are judiciously chosen as standardC4units of 1,3-diene precursors. The reactions are believed to undergo a unique cutting and insertion process, involving a CC bond cleavage of the enaminone and insertion of a newC(sp2) source with the formation of two C-C single bonds. A broad range of substrates can be used to synthesize the corresponding 1,3-dienes under very mild reaction conditions, including low catalyst-loading, ambient temperature, and a neutral reaction solvent.
- Jiang, Chengzhou,Wu, Jiamin,Han, Jiabin,Chen, Kai,Qian, Yang,Zhang, Zhengyu,Jiang, Yaojia
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supporting information
p. 5710 - 5713
(2021/06/16)
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- I2-Promoted [4 + 2] cycloaddition of: In situ generated azoalkenes with enaminones: Facile and efficient synthesis of 1,4-dihydropyridazines and pyridazines
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A facile and efficient strategy for the synthesis of 1,4-dihydropyridazines and pyridazines through I2-promoted [4 + 2] cycloaddition of in situ generated azoalkenes with enaminones has been developed. The switch in selectivity is attributed to the judici
- Baell, Jonathan B.,Feng, Jiajun,He, Tiantong,Huang, Fei,Xie, Yuxing,Yu, Yang
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supporting information
p. 9483 - 9493
(2020/12/15)
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- METHOD FOR PRODUCING NITROGEN-CONTAINING COMPOUND
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Provided is an efficient and economical production method of a nitrogen-containing compound. A method for producing a compound represented by the formula R3C(O)CH═CHNR1R2, including reacting a compound represented by the following formula (4) with more than 6-fold moles of a compound represented by the formula NR1R2C(O)H to give a reaction mixture of the compound represented by the formula (4) and the compound represented by the formula NR1R2C(O)H, and reacting the reaction mixture with a compound represented by the formula R3C(O)CH3 by using a basic compound: wherein X is a halogen atom and R1, R2 and R3 are each independently an alkyl group having 1-6 carbon atoms.
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Paragraph 0086-0095
(2020/02/20)
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- The use of enaminones and enamines as effective synthons for MSA-catalyzed regioselective synthesis of 1,3,4-tri- And 1,3,4,5-tetrasubstituted pyrazoles
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In the present work, an efficient regioselective synthesis of 1,3,4-tri- and 1,3,4,5-tetrasubstituted pyrazoles via a methanesulfonic acid (MSA)-catalyzed reaction of hydrazones with enaminones or enamines is reported. Mechanistically, the formation of the title compounds involves the [2+3] cycloaddition of hydrazones with enaminones or enamines followed by aromatization with acid and oxygen. This convenient method under mild conditions with various hydrazones, enaminones, and enamines was well-tolerated to afford products in good to excellent yields. Compared with the literature methods, this strategy has advantages such as materials that are available economically, metal-free catalysis, excellent regioselectivity, and high efficiency.
- Duan, Liancheng,Zhou, Hui,Gu, Yucheng,Gong, Ping,Qin, Mingze
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supporting information
p. 16131 - 16137
(2019/11/03)
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- Compound preparation method
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The invention relates to a compound preparation method. Organic solvents and sodium methylate are added into a reaction vessel, carbon monoxide is led into the reaction vessel to perform reaction, acetone and organic solvent mixed solution is dropped after reaction to continue reaction to generate an intermediate sodium salt as shown in a formula I, the intermediate sodium salt reacts with dimethylamine to generate 4-N, N-dimethyl butene-3-ketone as shown in a formula II. Synthesis steps can be finished in one vessel, and the compound preparation method is low in cost and suitable for industrialization production.
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Paragraph 0017-0026
(2019/04/17)
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- METHOD FOR THE PREPARATION OF 3-FLUOROALKYL-1-METHYLPYRAZOL-4-CARBOXYLIC ACID
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The present invention relates to method for the preparation of 3-fluoroalkyl-1-methylpyrazol-4-carboxylic acid, wherein it comprises the following steps: step 1, fluoroacetyl fluoride derivative shown in Formula I undergoes condensation with dimethylamino vinyl methyl ketone, as a result, 3-dimethylamino methylene-fluoro-2,4-pentanedione derivative shown in Formula II is formed; step 2, ring closing reaction takes place between said 3-dimethylamino methylene-fluoro-2,4-pentanedione shown in Formula II and methylhydrazine, in this way, 3-fluoroalkyl-1-methyl-4-acetyl pyrazol derivative shown in Formula III is obtained; step 3, the said 3-fluoroalkyl-1-methyl-4-acetyl pyrazol derivative shown in Formula III is oxidized in the presence of alkali, and then acidified, in this way, 3-fluoroalkyl-1-methylpyrazol-4-carboxylic acid shown in Formula IV is formed. Preparing method of present invention, wherein the required preparing route is simple, the raw material cost is low, the resulting yield of each step is high, and it is suitable for industrialization.
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Paragraph 0033
(2018/10/19)
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- COMPOSITION COMPRISING 3-(HALOALKYL OR FORMYL)-1H-PYRAZOLE-4-CARBOXYLIC ACIDS OR ESTERS, ITS MANUFACTURE AND ITS USE FOR THE PREPARATION OF CARBOXAMIDES
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The present invention concerns compositions comprising (i) a 3-(haloalkyl or formyl)-1H-pyrazole wherein R1 is a halogenated C1-4alkyl group, or the group -C(O)H, R2 is selected from the group consisting of H, C1-C12 alkyl, C2-C6 alkenyl, cycloalkyl, aryl, heteroaryl, aralkyl, each of which is optionally substituted, R3 is selected from the group consisting of H, C1-C12 alkyl, C2- C6 alkenyl, aryl or C3-C8 cycloalkyl, each of which is optionally substituted, and R4 is selected from the group consisting of H, X', COOR', OR', SR', C(O)NR'2, and (ii) at least one of the pyrazole derivatives of the formulae (II) - (X), (XVIIIa), (XVIIIb), (XIX) and (XX), wherein the chemical composition comprises equal to or more than 95 w% of compound of formula (I), its manufacture and use in processes for the manufacture of agrochemical or pharmaceutical pyrazole-4-carboxamide compounds.
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Page/Page column 21
(2017/12/01)
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- PROCESS FOR THE MANUFACTURE OF CARBOXAMIDES
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The present invention concerns a process for the manufacture of carboxamides, in particular agrochemical or pharmaceutically active ingredients, from pyrazole ketone compounds.
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Page/Page column 24
(2017/09/08)
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- Preparation method of 3-fluoroalkyl-1-methylpyrazol-4-carboxylic acid
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The invention relates to a preparation method of 3-fluoroalkyl-1-methylpyrazol-4-carboxylic acid. The method comprises the following steps: step 1, making a fluoroacetyl halide derivative shown in the formula I and dimethylamino vinyl methyl ketone to undergo a condensation reaction to generate a 3-dimethylamino methylene-1,1-difluoro-2,4-pentanedione derivative shown in the formula II; step 2, reacting the 3-dimethylamino methylene-1,1-difluoro-2,4-pentanedione derivative shown in the formula II with methylhydrazine for a ring-closing reaction to generate a 3-fluoroalkyl-1-methyl-4-acetyl pyrazole derivative shown in the formula III; and step 3, oxidizing the 3-fluoroalkyl-1-methyl-4-acetyl pyrazole derivative shown in the formula III in an alkaline condition, and performing acidification to generate 3-fluoroalkyl-1-methylpyrazol-4-carboxylic acid. The preparation method is short in reaction route, low in raw material cost, high in reaction yield of each step, and suitable for industrial production.
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Paragraph 0040; 0041
(2017/08/28)
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- Metal-Free Route for the Synthesis of 4-Acyl-1,2,3-Triazoles from Readily Available Building Blocks
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Functionalized 1,2,3-triazole heterocycles have been known for a long time and hold an extraordinary potential in diverse research areas ranging from medicinal chemistry to material science. However, the scope of therapeutically important 1-substituted 4-acyl-1H-1,2,3-triazoles is much less explored, probably due to the lack of synthetic methodologies of good scope and practicality. Here, we describe a practical and efficient one-pot multicomponent reaction for the synthesis of α-ketotriazoles from readily available building blocks such as methyl ketones, N,N-dimethylformamide dimethyl acetal, and organic azides with 100 % regioselectivity. This reaction is enabled by the in situ formation of an enaminone intermediate followed by its 1,3-dipolar cycloaddition reaction with an organic azide. We effectively utilized the developed strategy for the derivatization of various heterocycles and natural products, a protocol which is difficult or impossible to realize by other means.
- Thomas, Joice,Goyvaerts, Vince,Liekens, Sandra,Dehaen, Wim
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supporting information
p. 9966 - 9970
(2016/07/19)
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- PROCESS FOR PRODUCING 3-SUBSTITUTED THIOPHENE
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A process for producing a 3-substituted thiophene represented by the general formula (2): (wherein R represents cyano, formyl, carboxy, optionally substituted hydrocarbyloxycarbonyl, or optionally substituted acyl), characterized by reacting a vinyl compound represented by the general formula (1): RCH=CHY (wherein R has the same meaning as defined above; and Y is a leaving group) with α-mercaptoacetaldehyde or a polymer thereof.
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Page/Page column 14
(2008/06/13)
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- One-pot synthesis of some 2H-pyran-2-one derivatives
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A one-pot synthesis of various 2H-pyran-2-one derivatives 5-19 starting from methyl ketones 1, N,N-dimethylformamide dimethyl acetal and N-acylglycines 3 in acetic anhydride is described.
- Kepe, Vladimir,Kocevar, Marijan,Polanc, Slovenko
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p. 1707 - 1710
(2007/10/03)
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- ORTHOAMIDES, XLVIII REACTIONS OF AN AZAVINYLOGUE AMINALESTER WITH CH2-ACIDIC COMPOUNDS
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Condensation reactions of azavinylogue orthoamides 5a and 6a with CH2-acidic compounds are described.Reaction products are formylated - or azavinylogue formylated compounds 8 and 9 resp.The condensation reactions of 5a can be enhanced by addition of trimethyl borate.Under these conditions the formylations reaction-leading to compounds of type 8 - is preferred.
- Kantlehner, Willi,Hauber, Michael
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p. 697 - 704
(2007/10/02)
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- REACTION OF 1-DIALKYLAMINO-1-BUTYN-3-ONES WITH HYDRAZINE AND SUBSTITUTED HYDRAZINES
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A series of 1-dialkylmino-1-butyn-3-ones were obtained, and their reactions with hydrazine and its alkyl, aryl and unsymmetrical dialkyl derivatives were studied.The reactions with unsubstituted and monosubstituted hydrazones lead to the formation of heterocyclic compounds of the pyrazole series, while the monosubstituted hydrazines form two isomeric products.Unsymmetrical dimethylhydrazine adds at the C1-carbon atom with the formation of compounds containing an open structure.
- Ostroumov, I. G.,Tsil'ko, A. E.,Maretina, I. A.,Petrov, A. A.
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p. 1467 - 1474
(2007/10/02)
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- SYNTHESIS OF DERIVATIVES OF 3-OXOBUTANAL CONTAINING FUNCTIONAL GROUPS IN THE MESOMETHYLENE UNIT
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The synthesis of 2-bromo-3-oxobutanal was realized by the bromination of 1-dialkylamino-1-buten-3-ones.The trans-enol form predominates in solutions.The direct nitration of 1,1-diethoxy-3-butanol leads to 2-nitro-3-oxobutanal.
- Zaichenko, Yu. A.,Kormer, M. V.,Vil'davskaya, A. I.,Rall', K. B.,Maretina, I. A.
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p. 818 - 820
(2007/10/02)
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