- Auto-Tandem Catalysis-Induced Synthesis of Trisubstituted Furans through Domino Acid-Acid-Catalyzed Reaction of Aliphatic Aldehydes and 1,3-Dicarbonyl Compounds by using N-Bromosuccinimide as Oxidant
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A simple aluminium(III) chloride-catalyzed synthesis of tri-substituted furans from aliphatic aldehydes and 1,3-dicarbonyl compounds was developed by using N-bromosuccinimide (NBS) as an oxidant. This method was effective for the synthesis of various furan derivatives. Some of the products were not accessible with the previously reported methods. Mechanically, this reaction involved an auto-tandem catalysis based on a newly reported acid-acid-catalyzed tandem reaction to ensure that furans were successfully synthesized. (Figure presented.).
- Huang, Wenbo,Liu, Changhui,Gu, Yanlong
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p. 1811 - 1818
(2017/06/09)
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- Synthesis and biological evaluation of 3-phenyl-3-aryl carboxamido propanoic acid derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26A1)
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All-trans-retinoic acid (ATRA), the biologically active metabolite of vitamin A, is used medicinally for the treatment of hyperproliferative diseases and cancers. However, it is easily metabolized. In this study, the leading compound S8 was found based on virtual screening. To improve the activity of the leading compound S8, a series of novel S8 derivatives were designed, synthesized and evaluated for their in vitro biological activities. All of the prepared compounds showed that substituting the 5-chloro-3-methyl-1-phenyl-1H-pyrazole group for the 2-tertbutyl-5-methylfuran scaffold led to a clear increase in the biological activity. The most promising compound 32, with a CYP26A1 IC50 value of 1.36 μM (compared to liarozole (IC50 = 2.45 μM) and S8 (IC50 = 3.21 μM)) displayed strong inhibitory and differentiation activity against HL60 cells. In addition, the study focused on the effect of β-phenylalanine, which forms the coordination bond with the heme of CYP26A1. These studies suggest that the compound 32 can be used as an appropriate candidate for future development.
- Zhao, Dongmei,Sun, Bin,Ren, Jinhong,Li, Fengrong,Song, Shuai,Lv, Xuejiao,Hao, Chenzhou,Cheng, Maosheng
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p. 1356 - 1365
(2015/03/04)
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- Cu(I)-catalyzed reaction of diazo compounds with terminal alkynes: A direct synthesis of trisubstituted furans
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A method for the synthesis of tri-substituted furans has been developed based on Cu(I)-catalyzed reaction of terminal alkynes with β-keto α-diazoesters. This method for the synthesis of 2,3,5-trisubstituted furans is operationally simple and applicable to
- Hossain, Mohammad Lokman,Ye, Fei,Zhang, Yan,Wang, Jianbo
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p. 6957 - 6962
(2015/03/14)
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- One-pot synthesis of furans using base- and acid-supported reagents Na 2CO3/Al2O3-PPA/SiO2'
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A convenient method for the one-pot synthesis of furans from -keto esters and -halo ketones was developed using an acid- and base-supported reagent system Na2CO3/Al2O3-PPA/SiO2'. The condensation reaction of triketones, which are formed from the reaction of -keto esters with -halo ketones in the presence of Na2CO 3/Al2O3, was promoted by PPA/SiO2 to give the corresponding furans in good yields. This method is simple and easy to perform in comparison with stepwise processes, and the yields are good.
- Aoyama, Tadashi,Nagaoka, Takashi,Takido, Toshio,Kodomari, Mitsuo
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experimental part
p. 619 - 625
(2011/04/15)
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- HETEROCYCLIC COMPOUND
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The present invention provides a heterocyclic compound represented by the following formula (I), which has a glucagon antagonistic action and is useful for the prophylaxis or treatment of diabetes and the like, a compound represented by wherein ring A is an optionally substituted benzene ring and the like; Y is a nitrogen atom and the like; X is -O- and the like; R4 is a hydrogen atom and the like; R5 and R6 are each independently a hydrogen atom and the like; R1 is an optionally substituted hydrocarbon group and the like; R2 is a hydrogen atom and the like; and R3 is -(CH2)3-COOH and the like, or a salt thereof.
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Page/Page column 85
(2010/08/07)
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- 2,3,4- or 2,3,5-trisubstituted furans: Catalyst-controlled highly regioselective ring-opening cycloisomerization reaction of cyclopropenyl ketones
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2,3,4- or 2,3,5-trisubstituted furans were highly regioselectively formed from the cycloisomerization reaction of the same starting cyclopropenes 1 via the subtle choice of the transition metal halides. Under the catalysis of 5 mol % PdCl2(CHs
- Ma, Shengming,Zhang, Junliang
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p. 12386 - 12387
(2007/10/03)
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- (HALOMETHYLFURAN)CARBOXYLIC ESTERS IN THE MICHAELIS-BECKER REACTION
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Chloromethyl derivatives of furancarboxylic esters react with sodium diethyl phosphite only in accordance with the classical Michaelis-Becker scheme, but corresponding (bromoethyl)furans are subjected to nucleophilic as well as halogenophilic attack by the phosphite anion.The C-Br bond in 2-(bromomethyl)furans is polarized under the influence of the ring much more strongly than in 3-(bromomethyl) derivatives.The composition of products of the reaction between 2-(bromomethyl)furans and sodium diethyl phosphite shows that halogenophilic attack takes place only if the bromomethyl group is conjugated with the ethoxycarbonyl, the action of the latter being transmitted better from the 5 position than from the 3 position. 3-(Bromomethyl)furans give dehalogenation products only if the ethoxycarboxylic group is in the 2 position.Its influence from the 4 position is transmitted more weakly, and in this case halogenophilic attack does not occur.
- Pevzner, L. M.,Ignat'ev, V. M.,Ionin, B. I.
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p. 658 - 662
(2007/10/02)
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- CONVERSION OF 1,3-DICARBONYLS TO 1,4-DICARBONYLS
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The cyclopropanation of β-trimethylsiloxy α,β-unsaturated esters and ketones, prepared from 1,3-dicarbonyl compounds, with carbenes followed by ring cleavage gave corresponding 1,4-dicarbonyl compounds in moderate yields.
- Saigo, Kazuhiko,Kurihara, Hiroshi,Miura, Hisao,Hongu, Akinori,Kubota, Naomi,et al.
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p. 787 - 796
(2007/10/02)
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