- Johnson-Corey-Chaykovsky fluorocyclopropanation of double activated alkenes: Scope and limitations
-
Johnson-Corey-Chaykovsky fluorocyclopropanation of double activated alkenes utilizing S-monofluoromethyl-S-phenyl-2,3,4,5-tetramethylphenylsulfonium tetrafluoroborate is an efficient approach to obtain a range of monofluorocyclopropane derivatives. So far, fluoromethylsulfonium salts have displayed the broadest scope for direct fluoromethylene transfer. In contrast to more commonly used fluorohalomethanes or freon derivatives, diarylfluoromethylsulfonium salts are bench stable, easy-to use reagents useful for the direct transfer of a fluoromethylene group to alkenes giving access to the challenging products-fluorocyclopropane derivatives. Interplay between the reactivity of the starting materials and stability of the fluorocyclopropanes formed determines the outcome of the process.
- Kazia, Armands,Melngaile, Renate,Mishnev, Anatoly,Veliks, Janis
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supporting information
p. 1384 - 1388
(2020/03/03)
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- ISOINDOLINES AS HDAC INHIBITORS
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The present disclosure relates to inhibitors of zinc-dependent histone deacetylases (HDACs), having the formula: (I) wherein Z, X1, X2, Y1, Y2, Y3, L, Z, and R are described herein.
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-
Paragraph 00253
(2019/11/12)
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- Vanadium-Catalyzed Condensation of Ethyl Cyanoacetate with Ketones
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Vanadium compounds and complexes activated by pyridine or morpholine catalyze condensation of ethyl cyanoacetate with ketones and aldehydes leading to alkylidenecyanoacetates in 75–100% yield.
- Khusnutdinov,Shchadneva,Mayakova, Yu. Yu.
-
p. 403 - 409
(2018/04/24)
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- Copper-Mediated, Heterogeneous, Enantioselective Intramolecular Buchner Reactions of α-Diazoketones Using Continuous Flow Processing
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Enantioselective intramolecular Buchner reactions of α-diazoketones can be effected using heterogeneous copper-bis(oxazoline) catalysts in batch or using continuous flow processing in up to 83% ee. The catalyst can be reused up to 7 times without loss of activity. For α-diazoketones 3 and 4, the enantioselection achieved in flow with the immobilized catalyst was comparable with the standard homogeneous catalyzed process.
- Crowley, Daniel C.,Lynch, Denis,Maguire, Anita R.
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p. 3794 - 3805
(2018/04/14)
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- PIPERIDINE COMPOUNDS AS PCSK9 INHIBITORS
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One aspect of the invention relates to a series of new PCSK9 inhibitor compounds comprising piperidine ring structures, including compounds of formula (I) and/or pharmaceutically acceptable salts thereof. Another aspect of the invention relates to methods of treating PCSK9 receptor related diseases comprising administration of one or more compounds of formula (I) or a pharmaceutically acceptable salt thereof.
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-
Paragraph 0373; 0374; 0375
(2018/11/21)
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- Flash preparation of carbenoids: A different performance of cyanogen bromide
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Cyanogen halides are known substances for the cyanating reaction. There are a few evidences for bromination reaction too. On the other hand carbenes are known as very important substances due to their remarkable reactions. Unfortunately carbenes at room temperature are very unstable and there is not a simple method for preparation of them. In most cases the isolation is not possible. We have reported a new reliable and fast preparation method of almost stable carbenoids. The mechanism of the formation has been discussed.
- Hedayati, Mohammad Jalilzadeh,Pesyan, Nader Noroozi
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p. 2081 - 2089
(2015/04/22)
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- HETEROCYCLIC COMPOUNDS AND USES THEREOF
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Compounds and pharmaceutical compositions of formulae (I), (XI) and (XII) as PI3 kinase modulators and their use in the treatment of diseases such as cancer.
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Paragraph 00545
(2013/03/26)
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- HETEROCYCLIC COMPOUNDS AND USES THEREOF
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Compounds and pharmaceutical compositions that modulate kinase activity, including PI3 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including PI3 kinase activity, are described herein.
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-
Paragraph 00716-00717; 00790
(2013/03/26)
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- Efficient protocol for knoevenagel condensation in presence of the diazabicyclo[5.4.0]undec-7-ene-water complex
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A simple and efficient protocol for Knoevenagel condensation has been developed in the presence of diazabicyclo[5.4.0]undec-7-ene (DBU)/water complex. A widely range of carbonyl compounds (aliphatic and aromatic aldehydes, ketones) could react smoothly with methylene active ingredients (malononitrile, ethyl cyanoacetate, diethyl malonate and acetylacetone), which can not proceed by conven- tional catalyst. Other significant features of this method include readily work-up, good recyclability of catalytic system and short reaction time.
- Ying, An-Guo,Wu, Cheng-Lin,He, Guang-Hong
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experimental part
p. 653 - 656
(2012/07/28)
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- Schiff base structured acid-base cooperative dual sites in an ionic solid catalyst lead to efficient heterogeneous knoevenagel condensations
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An acid-base bifunctional ionic solid catalyst [PySaIm]3PW was synthesized by the anion exchange of the ionic-liquid (IL) precursor 1-(2-salicylaldimine)pyridinium bromide ([PySaIm]Br) with the Keggin-structured sodium phosphotungstate (Na
- Zhang, Mingjue,Zhao, Pingping,Leng, Yan,Chen, Guojian,Wang, Jun,Huang, Jun
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p. 12773 - 12782
(2012/11/07)
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- Total syntheses of (±)-(Z)- and (±)-(E)-9-(bromomethylene)-1, 5,5-trimethylspiro[5.5]undeca-1,7-dien-3-one and (±)-majusculone
-
A new total synthesis of the chamigrene sesquiterpenoids (Z)-9-(bromomethylene)-1,5,5-trimethylspiro[5.5]undeca-1,7-diene-3-one and its 15-E-epimer has been accomplished in 13 steps. In our sequence, a Diels-Alder reaction and subsequent reductive alkylat
- Zhu, Jia-Liang,Huang, Po-Wei,You, Ruei-Yi,Lee, Fa-Yan,Tsao, Sheng-Wei,Chen, I-Chia
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experimental part
p. 715 - 722
(2011/04/24)
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- One-pot new barbituric acid derivatives derived from the reaction of barbituric acids with BrCN and ketones
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Reaction of cyclic β-dicarbonyl compounds such as pyrimidine-(1 H,3H,5H)-2,4,6-trione (BA), 1,3-dimethyl pyrimidine-(1 H,3H,5H)-2,4,6-trione (DMBA) and 2-thioxo-pyrimidine-(1 H,3H,5H)-4,6-dione (TBA) with cyanogen bromide in acetone and 2-butanone in the presence of triethylamine afforded a new class of stable heterocyclic spiro[furo[2,3-d]pyrimidine-6,5′-pyrimidine]2, 2′,4,4′,6′(3H,3′H,5H)-penta-ones (dimeric forms of barbiturate) at 0 °C and ambient temperature. Structure elucidation was carried out by X-ray crystallographic, 1H NMR, 13C NMR, two dimensional NMR, FT-IR spectra, mass spectrometry and elemental analysis. The mechanism of product formation is discussed. The reaction of DMBA with cyanogen bromide in the presence of triethylamine also afforded trimeric form of barbiturate of uracil derivatives in good yield. The reaction of selected acyclic β-dicarbonyl compounds with cyanogen bromide in the presence of triethylamine in acetone and/or diethyl ether has also been investigated under the same condition. Diethyl malonate and ethyl cyanoacetate brominated and also ethyl acetocetate both bro-minated and cyanated on active methylene via cyanogen bromide.
- Hosseini, Yaser,Rastgar, Saeed,Zerrin Heren,Orhan Büyükgüng?r,Pesyan, Nader Noroozi
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experimental part
p. 309 - 318
(2011/11/06)
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- Bifunctional acid-base ionic liquid organocatalysts with a controlled distance between acid and base sites
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Bifunctional acid-base ionic liquid organocatalysts with different distances between the two sites have been synthesised, and their activity for the Knoevenagel condensation has been tested. As has been found to be the case with enzymes, the distance betw
- Boronat, Mercedes,Climent, Maria J.,Corma, Avelino,Iborra, Sara,Monton, Raquel,Sabater, Maria J.
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experimental part
p. 1221 - 1231
(2010/06/12)
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- The Knoevenagel reaction in water catalyzed by zwitterionic liquids
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Three hydroxyl functionalized zwitterionic liquids (ZILs) were found to be novel recyclable catalysts for the Knoevenagel condensation between aldehydes or ketones and active methylene compounds in aqueous medium. Both aldehydes and ketones gave satisfactory results. The products could simply be separated from the catalysts/water, and the catalysts could be recycled six times without noticeably decreasing the catalytic activity.
- Fang, Dong,Fei, Zheng-Hao,Liu, Zu-Liang
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experimental part
p. 799 - 803
(2009/09/28)
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- Ionic liquid as catalyst and reaction medium - A simple, efficient and green procedure for Knoevenagel condensation of aliphatic and aromatic carbonyl compounds using a task-specific basic ionic liquid
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The basic ionic liquid 1-butyl-3-methylimidazolium hydroxide, [bmIm]OH, efficiently catalyzes Knoevenagel condensation without requirement of any organic solvent. A wide range of aliphatic and aromatic aldehydes and ketones easily undergo condensations with diethyl malonate, malononitrile, ethyl cyanoacetate, malonic acid and ethyl acetoacetate. The reactions proceed at room temperature and are very fast (10-30 min). However, the most significant feature of this methodology is the condensation of aliphatic aldehyde with diethyl malonate, which is not very easy to achieve by conventional reagents, and was not addressed adequately in literature providing a general and convenient procedure. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Ranu, Brindaban C.,Jana, Ranjan
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p. 3767 - 3770
(2007/10/03)
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- SYNTHESIS OF 3-AMINO-2-CHLORO-4-METHYLPYRIDINE FROM ACETONE AND ETHYL CYANOACETATE
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A method for making 3-amino-2-chloro-4-methylpyridine from acetone and ethyl cyanoacetate, as depicted in the following reaction scheme.
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-
Page/Page column 5
(2010/02/14)
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- THIENOPYRIMIDINE DERIVATIVES AS POTASSIUM CHANNEL INHIBITORS
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The present invention provides thienopyrimidine compounds which are potasium channels inhibitors. Pharmaceutical compositions comprising the compounds and their use in the treatment of arrhythmia are also provided.
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-
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- Organic Reactions in Ionic Liquids: Knoevenagel Condensation Catalyzed by Ethylenediammonium Diacetate
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The moisture and air stable ionic liquids 1-butyl-3-methylimidazonium tetrafluoroborate [bmim]BF4 and 1-butyl-3-methylimidazonium hexafluorophosphate [bmim]PF6 were used as 'green' recycle alternatives to volatile organic solvents (VOCs) for ethylenediammonium diacetate (EDDA) catalyzed Knoevenagel condensation between aldehydes or ketones with active methylene compounds. Both aldehydes and ketones gave satisfactory results. The ionic liquids containing catalyst EDDA were recycled several times with no decrease in yields and reaction rates. In the case of 2-hydroxybenzaldehyde, the reactions led to the formation of 3-substituted coumarins under standard reaction conditions.
- Su, Ce,Chen, Zhen-Chu,Zheng, Qin-Guo
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p. 555 - 559
(2007/10/03)
-
- Steric effects in high pressure Knoevenagel reactions
-
The pressure effect in Knoevenagel condensations involving ketones and ethyl cyanoacetate is studied. The reactions are diversely affected. For cyclic ketones there is a small effect on the reaction yield. However, in the case of acyclic ketones, the sensitivity of the reaction to pressure increases with increasing steric congestion of the ketone. Such a result highlights the synthetic utility of high pressure for the preparation of hindered functionalized alkenes.
- Jenner, Gérard
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p. 243 - 245
(2007/10/03)
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- Synthesis of 3-amino-2-chloro-4-methylpyridine from acetone and ethyl cyanoacetate
-
A method for making 3-amino-2-chloro-4-methylpyridine from acetone and ethyl cyanoacetate, as depicted in the following reaction scheme.
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-
-
- Synthesis of nitrogen-containing heterocycles. 7 reaction of aliphatic diaminomethylenehydrazones with hindered ethoxymethylenecyanoacetate
-
Aliphatic diaminomethylenehydrazones 1 were reacted with ethyl 2-cyano-3-ethoxy-2-pentenoate 2 to give a number of heterocycles in low to moderate yields, according to the substitution pattern and the size of substituent. When 1 carried a single methyl group on the terminal nitrogen, it gave preferentially 6-oxo-1,6-dihydropyrimidines 4 incorporating N(4) into the ring. In contrast, the reaction between 1c or 1d and 2 led to 6-imino- and 6-oxo-1,6-dihydropyrimidines 7 and 8 along with 3. When the alkylidene moiety was bulky, 1e and 1f, the similar reaction gave 3 in high yields without any cyclized product. Upon exposure to acid, compound 3 yielded 6-oxo-1,6-dihydropyrimidines 6, [1,2,4]triazolo[1,5-c]pyrimidine-8-carboxylate 5 and N-alkenyl-1,2,4-triazoles 9 in addition to 7 and 8 in proportions dictated by the nature of the substituents of 1. The structural assignment and reaction mechanism are discussed.
- Miyamoto, Yoshiko,Yamazaki, Chiji
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p. 1285 - 1289
(2007/10/03)
-
- Transition metal polyhydrides-catalyzed addition of activated nitriles to aldehydes and ketones via Knoevenagel condensation
-
Transition metal polyhydrides and dihydrogen complexes catalyze Knoevenagel addition of cyanoacetate to aldehydes and ketones under neutral and mild conditions, the adducts undergo dehydration to give substituted (E)-2-cyano-α,β-unsaturated esters exclusively.
- Lin, Yingrui,Zhu, Xianchao,Xiang, Min
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p. 215 - 218
(2007/10/02)
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- MECHANISM OF INTRAMOLECULAR CYCLOALKYLATION OF 3-METHYL-3-PHENYL-1-BUTANOL IN THE PRESENCE OF D3PO4
-
The intramolecular cycloalkylation of isomeric 2-methyl-4-phenyl-2-butanol and 3-methyl-3-phenyl-1-butanol in D3PO4 is accompanied by hydrogen exchange with the formation of deuterated 1,1-dimethylindane.The distribution of the deuterium in the polymethylene ring shows that the reaction of the first alcohol takes place as a result of C5-cyclization of the χ-phenylalkyl cation, whereas the reaction of the second alcohol takes place by direct C5-cyclization and by cyclization of the χ-phenylalkyl cations formed as a result of 1,2- and 1,3-transfers of the phenyl group.
- Sakhabutdinov, A. G.,Usmanova, A. G.,Frolov, P. A.,Kushnarev, D. F.,Schmidt, F. K.
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p. 1452 - 1455
(2007/10/02)
-
- A Synthesis of Pyrroloquinazolinones, Indoloquinazolinones, Pyrrolothienopyrimidinones, Benzothienopyrrolopyrimidinones and 6H-Cycloheptathienopyrrolopyrimidinones
-
α-Cyano-γ-halo-crotonnitriles (1) synthesized (e.g. via Knoevenagel reaction and by subsequent halogenation) react with primary arylamines (2) to substituted 1-aryl-2-amino-3-cyano-pyrroles (3).We found that the reaction yields pyrroloquinazolin-5-
- Suesse, M.,Johne, S.
-
p. 647 - 653
(2007/10/02)
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