- Regioselective N-1 and C-2 diacylation of 3-substituted indoles with arylglyoxal hydrates for the synthesis of indolyl diketones
-
A highly regioselective N-1 and C-2 diacylation of 3-substituted indoles with arylglyoxal hydrates to afford N-1 and C-2 indolyl diketones in moderate to good yields is described. Notably, the control of regioselectivity is achieved by small changes in the Cu catalyst, additive and solvent. Importantly, the intermediates for N-1 and C-2 diacylation were detected and two plausible pathways were also proposed.
- Pan, Dalong,Chu, Jinpeng,Gao, Xianrui,Wang, Cuiping,Meng, Qingtao,Chi, Haijun,Dong, Yan,Duan, Chunying,Zhang, Zhiqiang
-
supporting information
p. 6998 - 7003
(2018/10/17)
-
- Catalytic asymmetric Meerwein-Ponndorf-Verley reduction of glyoxylates induced by a chiral N,N′-dioxide/Y(OTf)3 complex
-
An asymmetric Meerwein-Ponndorf-Verley (MPV) reduction of glyoxylates was for the first time accomplished via an N,N′-dioxide/Y(OTf)3 complex with aluminium alkoxide and molecular sieves (MSs) as crucial additives. A variety of optically active α-hydroxyesters were obtained with excellent results. A possible reaction mechanism was proposed based on the experiments.
- Wu, Wangbin,Zou, Sijia,Lin, Lili,Ji, Jie,Zhang, Yuheng,Ma, Baiwei,Liu, Xiaohua,Feng, Xiaoming
-
supporting information
p. 3232 - 3235
(2017/03/20)
-
- Synthesis and X-ray Characterization of Alkali Metal 2-Acyl-1,1,3,3-tetracyanopropenides
-
A novel route for synthesis of 2-acyl-1,1,3,3-tetracyanopropenides (ATCN) salts in high yields and excellent purities starting from readily available methyl ketones, malononitrile, bromine, and alkali metal acetates is reported. The starting aryl(heteroaryl) methyl ketones were oxidized to the corresponding α-ketoaldehydes by new a DMSO-NaBr-H2SO4 oxidation system in yields up to 90% within a short reaction time of 8-10 min. The subsequent stages of ATCN preparation are realized in aqueous media without use of any toxic solvents, in accordance with principle 5 of "green chemistry". Lithium, sodium, potassium, rubidium, and cesium 2-benzoyl-1,1,3,3-tetracyanopropenides were characterized by X-ray diffraction analysis. These salts show a good potential for synthesis of five- and six-membered heterocycles and may serve as potentially useful ligands in coordination and supramolecular chemistry.
- Karpov, Sergey V.,Grigor'Ev, Arthur A.,Kayukov, Yakov S.,Karpova, Irina V.,Nasakin, Oleg E.,Tafeenko, Victor A.
-
p. 6402 - 6408
(2016/08/16)
-
- Molybdate sulfuric acid-catalyzed one-pot synthesis of substituted coumarins under solvent-free conditions
-
An efficient method for the synthesis of new aryloylamido coumarins via a one-pot, three-component reaction of an aryl glyoxal, benzamide, and a 4-hydroxycoumarin in the presence of molybdate sulfuric acid under solvent-free conditions is reported. This h
- Khodabakhshi, Saeed,Karami, Bahador,Eskandari, Khalil
-
p. 7263 - 7272
(2015/09/29)
-
- Reaction of arylglyoxals with pyrrole or indole in aqueous media: Facile synthesis of heteroaryl α-acyloins
-
Pyrrole or indole reacts with arylglyoxal monohydrates in aqueous media in the absence of any catalyst to produce pyrrol-2-yl or indol-3-yl α-acyloin derivatives in high yields as the only product. Reactions were clean and products were isolated by simple filtration. When the reactions were carried out in acetonitrile as solvent, different products were obtained.
- Anary-Abbasinejad, Mohammad,Talebizadeh, Mahdiyeh
-
p. 963 - 968
(2014/08/05)
-
- Metal-free dual sp3 C-H functionalization: I2- promoted domino oxidative cyclization to construct 2,5-disubstituted oxazoles
-
An I2-promoted sp3 C-H functionalization has been developed for the synthesis of 2,5-disubstituted oxazoles from easily available methyl ketones and benzylamines without any metal and peroxide catalyst. This domino oxidative cyclization process involves the cleavage of C-H bond and the formation of C-N, C-O bonds.
- Gao, Qing-He,Fei, Zhuan,Zhu, Yan-Ping,Lian, Mi,Jia, Feng-Cheng,Liu, Mei-Cai,She, Neng-Fang,Wu, An-Xin
-
-
- Regiospecific synthesis of novel furo[4,5- c ]coumarins in a one-pot reaction
-
A new and expedient assembly of an interesting class of amido-substituted furo[4,5-c]coumarins has been successfully achieved through a one-pot sequential coupling and cyclization strategy starting from 4-hydroxycoumarin, aryl glyoxals and benz-amide. All
- Karami, Bahador,Khodabakhshi, Saeed,Eskandari, Khalil
-
p. 998 - 1000
(2013/06/27)
-
- A highly efficient and enantioselective intramolecular cannizzaro reaction under TOX/Cu(II) catalysis
-
An asymmetric intramolecular Cannizzaro reaction of aryl and alkyl glyoxals with alcohols has been realized with an unprecedented high level of enantioselectivity, on the basis of a newly developed congested TOX ligand and a gradual liberation protocol of active glyoxals from glyoxal monohydrates. Preliminary results suggested a mechanism of enantioselective addition of alcohols to glyoxals contributing most to the stereoselectivity, other than by the dynamic kinetic resolution of hemiacetal intermediates.
- Wang, Pan,Tao, Wen-Jie,Sun, Xiu-Li,Liao, Saihu,Tang, Yong
-
supporting information
p. 16849 - 16852
(2013/12/04)
-