cas 7194-78-7, 2-(3-broMophenyl)-2-oxoacetic acid

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Photoinduced homolytic decarboxylative acylation/cyclization of unactivated alkenes with α-keto acid under external oxidant and photocatalyst free conditions: access to quinazolinone derivatives
A novel and green strategy for the synthesis of acylated quinazolinone derivativesviaphoto-induced decarboxylative cascade radical acylation/cyclization of quinazolinone bearing unactivated alkenes has been developed. The protocol provides a novel route to access acyl radicals from α-keto acids through a self-catalyzed energy transfer process. Most importantly, the reaction proceeded smoothly without any external photocatalyst, additive or oxidant, and could be easily scaled-up in flow conditions with sunlight irradiation.
Sun, Bin,Shi, Rongcheng,Zhang, Kesheng,Tang, Xiaoli,Shi, Xiayue,Xu, Jiayun,Yang, Jin,Jin, Can
supporting information
p. 6050 - 6053
(2021/06/21)

Hypervalent Iodine(III)-Promoted Radical Oxidative C-H Annulation of Arylamines with α-Keto Acids
A novel catalyst-free radical oxidative C-H annulation reaction of arylamines with α-keto acids toward benzoxazin-2-ones synthesis under mild conditions was developed. This hypervalent iodine(III)-promoted process eliminated the use of a metal catalyst or additive with high levels of functional group tolerance. Hypervalent iodine(III) was both an oxidant and a radical initiator for this reaction. The synthetic utility of this method was confirmed by the synthesis of the natural product cephalandole A.
Long, Lipeng,Wang, Jieyan,Gu, Liuqing,Yang, Shiguang,Qiao, Liang,Luo, Guotian,Chen, Zhengwang
supporting information
p. 12084 - 12092
(2021/08/24)

Diazotrifluoroethyl Radical: A CF3-Containing Building Block in [3 + 2] Cycloaddition
We present herein a visible-light-induced [3 + 2] cycloaddition of a hypervalent iodine(III) reagent with α-ketoacids for the construction of 5-CF3-1,3,4-oxadiazoles that are of importance in medicinal chemistry. The reaction proceeds smoothly without a photocatalyst, metal, or additive under mild conditions. Different from the well-established trifluorodiazoethane (CF3CHN2), the diazotrifluoroethyl radical [CF3C(·)N2], a trifluoroethylcarbyne (CF3C?:) equivalent and an unusual CF3-containing building block, is involved in the present reaction system.
Zhao, Wen-Wen,Shao, Yong-Chao,Wang, An-Ni,Huang, Jia-Li,He, Chun-Yang,Cui, Bao-Dong,Wan, Nan-Wei,Chen, Yong-Zheng,Han, Wen-Yong
supporting information
p. 9256 - 9261
(2021/12/06)

Minisci aroylation of N-heterocycles using choline persulfate in water under mild conditions
Metal persulfate mediated thermal oxidative organic transformations invariably require a higher temperature and frequently use an organic solvent. The objective of this work was to develop persulfate mediated oxidative transformations that can be performed nearly at room temperature using water as a solvent. This report describes modified Minisci aroylation of isoquinolines with arylglyoxylic acids using choline persulfate and its pre-composition (choline acetate and K2S2O8) in water at 40 °C. A few other nitrogen heterocycles were also utilized affording various aroylated products in good to excellent yields. Unlike metal persulfate that could produce metal salt byproducts, a key feature of the chemistry reported herein includes the use of environmentally benign choline persulfate containing biodegradable choline as a counter-cation, the Minisci reaction demonstrated at 40 °C in water as the only solvent, and unconventional activation of persulfate. This journal is
Hunjan, Mandeep Kaur,Laha, Joydev K.,Tinwala, Ummehani
p. 22853 - 22859
(2021/12/24)

Selective photoredox decarboxylation of α-ketoacids to allylic ketones and 1,4-dicarbonyl compounds dependent on cobaloxime catalysis
A photoredox/cobaloxime co-catalyzed coupling reaction of α-ketoacids and methacrylates to obtain allylic ketones is described. Without the cobaloxime catalyst, 1,4-dicarbonyl compounds are generated. The cobaloxime catalyst enables dehydrogenation to generate the formation of new olefins. The generality, good substrate scope and mild conditions are good features in the photoredox/cobaloxime catalysis protocol, and this method will provide new opportunities for the functionalization of more olefins.
Zhang, Hong,Xiao, Qian,Qi, Xu-Kuan,Gao, Xue-Wang,Tong, Qing-Xiao,Zhong, Jian-Ji
supporting information
p. 12530 - 12533
(2020/11/02)

METHOD FOR PRODUCING BENZOYL FORMIC ACID COMPOUND AND PYRIDAZINE COMPOUND
The present invention provides an industrially-advantageous process for preparing a benzoyl formic acid compound, and an efficient process for preparing a pyridazine compound using the same process. Specifically, the present invention provides a process for preparing a compound represented by formula (2), which comprises a step (B): a step of reacting a compound represented by formula (1) with a nitrosyl sulfuric acid in water to produce the compound represented by formula (2).
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Paragraph 0104

(2020/12/18)

Novel synthesis method of benzene ring polysubstituted compound based on benzoyl formic acid
The invention relates to a novel synthesis method of a benzene ring polysubstituted compound based on benzoyl formic acid. According to the synthesis method, an acetophenone-based benzene ring polysubstituted compound is used as a raw material, a specific
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Paragraph 0027-0033; 0069-0075

(2020/05/30)

Tandem N, N-Dialkylation Reaction of N-Trimethylsilyl α-Iminoesters Utilizing an Umpolung Reaction and Characteristics of the Silyl Substituent: Synthesis of Pyrrolidine, Piperidine, and Iminodiacetate
Umpolung reactions of N-trimethylsilyl α-iminoester with organometallics gave directly N-alkylaminoesters in high yields without the need for removing a protecting group at the nitrogen atom. Efficient syntheses of pyrrolidines, piperidines, and iminodiacetate derivatives were also developed via tandem N,N- or N,C-dialkylation reactions utilizing characteristics of the silyl substituent. Furthermore, under the influence of silica gel, the addition of an enolate to the imino nitrogen proceeded to give an iminodiacetate derivative.
Mizota, Isao,Tadano, Yurie,Nakamura, Yusuke,Haramiishi, Tomoki,Hotta, Miyuki,Shimizu, Makoto
supporting information
p. 2663 - 2667
(2019/04/30)

Palladium-Catalyzed Primary Amine-Directed Decarboxylative Annulation of α-Oxocarboxylic Acids: Access to Indolo[1,2-a]quinazolines
An efficient protocol for the preparation of indolo[1,2-a]quinazolines via palladium-catalyzed decarboxylative annulation of indols with α-oxocarboxylic acids has been realized by using primary amine as a directing group (DG). This transformation proceeds smoothly with exclusive regioselectivity and represents an one-pot Domino synthesis of indo-lo[1,2-a]quinazolines from α-oxocarboxylic acids. (Figure presented.).
Jiang, Guangbin,Wang, Shoucai,Zhang, Jun,Yu, Jianwen,Zhang, Ziang,Ji, Fanghua
supporting information
p. 1798 - 1802
(2019/03/13)

Electrochemical synthesis of enaminones: Via a decarboxylative coupling reaction
An environmentally benign and efficient electrochemical synthesis of enaminones via a decarboxylative coupling reaction of α-keto acids using n-Bu4NI as a redox catalyst and electrolyte under constant current electrolysis in an undivided cell is reported. A broad vinyl azide substrate scope and high functional group tolerance are observed. A gram-scale reaction further demonstrates the practicability of the protocol. The results of cyclic voltammetry and control experiments indicate that I2 is likely the active species to initiate the oxidative decarboxylation via an acyl hypoiodite intermediate.
Kong, Xianqiang,Liu, Yulong,Lin, Long,Chen, Qianjin,Xu, Bo
supporting information
p. 3796 - 3801
(2019/07/31)

Copper/Persulfate-Promoted Oxidative Decarboxylative C?H Acylation of Pyrazolones with α-Oxocarboxylic Acids: Direct Access to 4-Acylpyrazolones under Mild Conditions
A facile and efficient oxidative C?H acylation of N-substituted pyrazolones using α-oxocarboxylic acids as an acyl group source was developed. A combination of Cu(OAc)2 and K2S2O8 enables the reaction to proceed smoothly under air and provides a wide array of 4-acylpyrazolone products in moderate to excellent yields. The mechanism of this transformation is believed to proceed via a copper-induced decarboxylation to form the acyl-copper species. This method provides a convenient and useful route for a direct installation of an acyl moiety into bioactive pyrazolone derivatives, which can be further utilized in many applications. (Figure presented.).
Kittikool, Tanakorn,Thupyai, Akkharaphong,Phomphrai, Khamphee,Yotphan, Sirilata
supporting information
p. 3345 - 3355
(2018/09/10)

Copper-catalyzed oxidative decarboxylative coupling of α-keto acids and sulfoximines
A copper-catalyzed oxidative decarboxylative coupling of α-keto acids with NH-sulfoximines has been developed. With CuBr as the catalyst and K2S2O8 as the oxidant, this reaction enables the formation of a C-N bond and gives N-aroylsulfoximine products in moderate to excellent yields. The reaction mechanism is likely to involve the generation of a reactive aroyl radical intermediate.
Pimpasri, Chaleena,Sumunnee, Ladawan,Yotphan, Sirilata
supporting information
p. 4320 - 4327
(2017/07/10)

Aldehydes as Carbon Radical Acceptors: Silver Nitrate Catalyzed Cascade Decarboxylation and Oxidative Cyclization toward Dihydroflavonoid Derivatives
Silver nitrate-catalyzed cascade decarboxylation and oxidative cyclization of α-oxocarboxylic acids, alkenes, and aldehydes is demonstrated for the first time. With ammonium persulfate as the oxidant, the cascade reactions afford dihydroflavonoid derivatives as products in moderate to good yields, exhibiting a broad substrate tolerance. Control experiments indicated that the mechanism includes a radical pathway with aldehydes as the carbon radical acceptors. (Figure presented.).
Yang, Wen-Chao,Dai, Peng,Luo, Kai,Ji, Yi-Gang,Wu, Lei
supporting information
p. 2390 - 2395
(2017/07/22)

A Copper(I)-Catalyzed Addition/Annulation Sequence for the Two-Component Synthesis of γ-Ylidenebutenolides
A highly efficient Cu(I)-catalyzed addition/annulation sequence has been developed for the synthesis of (Z)-ylidenebutenolides employing readily available α-ketoacids and alkynes as substrates. The reactions employ a simple commercially available Cu(I)-catalyst, display good substrate scope, and deliver products with high stereoselectivity. The synthetic utility of the method is demonstrated by the straightforward derivatization of the ylidenebutenolides into a diverse range of heterocycles, and also by the preparation of the natural product bovolide, and analogs thereof.
Seo, Sangwon,Willis, Michael C.
supporting information
p. 4556 - 4559
(2017/09/11)

GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES
Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).
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Paragraph 000969

(2015/04/15)

Synthesis of oxazoles by silver catalysed oxidative decarboxylation-cyclization of α-oxocarboxylates and isocyanides
A silver catalysed synthesis of oxazoles by the oxidative decarboxylation-cyclization of α-oxocarboxylates and isocyanides was developed. This method provided a novel strategy to construct oxazole rings compared to traditional methods. Mechanistic investigations such as operando IR, EPR and radical inhibition experiments were carefully done and confirmed the acyl cation and Ag(ii) as the intermediates in this transformation, and the involvement of a radical decarboxylative process.
Ma, Yiyang,Yan, Zhiyuan,Bian, Changliang,Li, Ke,Zhang, Xiaowen,Wang, Mengfan,Gao, Xinlong,Zhang, Heng,Lei, Aiwen
supporting information
p. 10524 - 10527
(2015/06/25)

Nickel-catalyzed decarboxylative acylation of heteroarenes by sp 2 C-H functionalization
Nickel-catalyzed ligand-free decarboxylative cross-coupling of azole derivatives with α-oxoglyoxylic acids has been developed. This work represents the first example of decarboxylative cross-coupling reactions, in a C-H bond functionalization manner, thro
Yang, Ke,Zhang, Cheng,Wang, Peng,Zhang, Yan,Ge, Haibo
supporting information
p. 7241 - 7244
(2014/06/23)

Cu(ii)-catalyzed decarboxylative acylation of acyl C-H of formamides with α-oxocarboxylic acids leading to α-ketoamides
CuBr2-catalyzed decarboxylative acylation of the acyl C-H of N-monosubstituted and N,N-disubstituted formamides with α-oxocarboxylic acids leading to α-ketoamides was developed, which generated the corresponding products in good yields. The Royal Society of Chemistry 2013.
Li, Dengke,Wang, Min,Liu, Jie,Zhao, Qiong,Wang, Lei
supporting information
p. 3640 - 3642
(2013/05/21)

Palladium-catalyzed decarboxylative coupling of α-oxocarboxylic acids with C(sp2)-H of 2-aryloxypyridines
An efficient palladium-catalyzed decarboxylative ortho-acylation of 2-aryloxypyridines with α-oxocarboxylic acids is described. In this new transformation, the aromatic C(sp2)-H bond was successfully acylated to give diverse aromatic ketones regioselectively in moderate to good yields. The pyridine group can be removed easily after the acylation to give the corresponding 2-hydroxy aromatic ketones. Copyright
Yao, Jinzhong,Feng, Ruokun,Wu, Zaihong,Liu, Zhanxiang,Zhang, Yuhong
supporting information
p. 1517 - 1522
(2013/06/27)

FUSED RING HETEROCYCLE KINASE MODULATORS
The present invention provides fused ring heterocycles as kinase modulators, pharmaceutical compositions containing these modulators, and methods of using these modulators to treat diseases mediated by kinase activity.
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(2008/12/04)

Kinetics and mechanism of the oxidation of some α-hydroxy carboxylic acids by [bis(trifluoroacetoxy)iodo]benzene
The oxidation of α-hydroxy carboxylic acids by [bis(trifluoroacetoxy) iodo]benzene (TFAIB), to the corresponding oxoacids is first order with respect to each, the hydroxy acid, TFAIB and hydrogen ions. The oxidation of α-deuteriomandelic acid (PhCDOHCO2H) exhibits the presence of a substantial primary isotope effect confirming the cleavage of the α - C - H bond in the rate-determining step. The rate of oxidation of substituted mandelic acids correlates well with Brown's σ+ values with large negative reaction constants. A mechanism involving transfer of a hydride ion from the hydroxy acid to the oxidant has been postulated.
Banerji, Jayshree,Sharma, Pradeep K.,Banerji, Kalyan K.
p. 445 - 448
(2008/02/09)

BIARYL SUBSTITUTED PYRAZINONES AS SODIUM CHANNEL BLOCKERS
Biaryl substituted pyrazinone compounds represented by Formula I, or pharmaceutically acceptable salts thereof. Pharmaceutical compositions comprise an effective amount of the instant compounds, either alone, or in combination with one or more other thera
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(2010/02/14)

Kinetics and Mechanism of the Oxidation of Some α-Hydroxy Acids by Benzyltrimethylammonium Dichloroiodate
The oxidation of lactic acid, mandelic acid, and ten monosubstituted mandelic acids by benzyltrimethylammonium dichloroiodate (BTMACI) in glacial acetic acid leads to the formation of the corresponding oxo acid. The reaction is first order with respect to hydroxy acid, BTMACI, and zinc chloride. An addition of benzyltrimethylammonium chloride enhances the rate slightly. [PhCH2Me3N](1+)[IZn2Cl6](1-) is postulated to be the reactive oxidizing species. The oxidation of α-deuteriomandelic acid exhibited the presence of a substantial kinetic isotope effect (kH/kD = 5.97 at 298 K). The rate of oxidation of the substituted mandelic acids showed an excellent correlation with Brown's ?+ values. The reaction constants are negative. A mechanism involving the transfer of hydride ion to the oxidant is postulated.
Goyal, Archana,Kothari, Seema
p. 2335 - 2340
(2007/10/03)

Kinetics and mechanism of oxidation of some α-hydoxy acids by butyltriphenylphosphonium dichromate
The oxidation of lactic acid, mandelic acid and nine monosubstituted mandelic acids by butyltriphenylphosphonium dichromate (BTPPD) in dimethylsulphoxide (DMSO) leads to the formation of the corresponding oxoacids. The reaction is first order in BTPPD. The order in the reductant and hydrogen ions is two. The oxidation of α-deuteriomandelic acid exhibited the presence of a substantial kinetic isotope effect. The reaction has been studied in nineteen organic solvents and the solvent effect analyzed using multiparametric equations. It is found that the cation-solvating power plays the major role. The rate of oxidation of substituted mandelic acids shows an excellent correlation with the Hammett σ values. The reaction constants are negative. Suitable mechanism has been proposed.
Kothari,Kothari,Banerji
p. 734 - 739
(2007/10/03)