- Method for synthesizing chiral spiro molecules based on chiral binaphthol
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The invention discloses a method for synthesizing chiral spiro molecules based on chiral binaphthol. The method comprises the following steps: firstly, obtaining corresponding propargyl carbonate frompropargyl alcohol or derivatives thereof and methyl chl
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Paragraph 0061-0065; 0131-0136
(2021/03/31)
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- Palladium-catalyzed [5+1] annulation of salicylic acid derivatives and propargylic carbonates
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A palladium-catalyzed annulation reaction between salicylic acid derivatives and propargylic carbonates via the cleavage of a propargylic carbonoxygen bond is described. This rare annulation reaction uses propargylic compounds as the C1 component for hete
- Sato, Kazuya,Ogiwara, Yohei,Sakai, Norio
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supporting information
p. 1595 - 1602
(2020/12/29)
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- Method for preparing propargyl methyl carbonate
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The invention discloses a method for preparing propargyl methyl carbonate. The method comprises the following steps: S1. raw material premixing; S2. normal-pressure heated reaction; S3. residue filtering; S4. rectification under vacuum, thereby obtaining the propargyl methyl carbonate. The method provided by the invention is safe, is low in cost and high in yield and can be used for extensively preparing the propargyl methyl carbonate.
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Paragraph 0019-0021
(2018/06/13)
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- Regioswitchable Palladium-Catalyzed Decarboxylative Coupling of 1,3-Dicarbonyl Compounds
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A palladium-catalyzed chemo- and regioselective coupling of 1,3-dicarbonyl compounds via an allylic linker has been developed. This reaction, which displays broad substrate scope, forms two C-C bonds and installs two all-carbon quaternary centers. The regioselectivity of the reaction can be predictably controlled by utilizing an enol carbonate of one of the coupling partners.
- Kenny, Miles,Christensen, Jeppe,Coles, Simon J.,Franckeviius, Vilius
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supporting information
p. 3926 - 3929
(2015/08/19)
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- Diels-Alder reactions of five-membered heterocycles containing one heteroatom
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Diels-Alder reactions of five-membered heterocycles containing one heteroatom with an N-arylmaleimide were studied. Cycloaddition of 2,5-dimethylfuran (4) with 2-(4-methylphenyl)maleimide (3) in toluene at 60 °C gave bicyclic adduct 5. Cycloadditions of 3 with 2,5-dimethylthiophene (11) and 1,2,5-trimethylpyrrole (14) were also studied. Interestingly, the bicyclic compound 5 cleanly rearranged, with loss of water, when treated with p-toluenesulfonic acid in toluene at 80 °C to give 4,7-dimethyl-2-p-tolylisoindoline-1,3-dione (6).
- Ding, Xiaoyuan,Nguyen, Son T.,Williams, John D.,Peet, Norton P.
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supporting information
p. 7002 - 7006
(2015/01/09)
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- HETEROCYCLIC COMPOUNDS AS MEK INHIBITORS
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The invention provides novel substituted heterocyclic compounds represented by Formula I and Formula II, or a pharmaceutically acceptable salt, solvate, polymorph, ester, tauntomer or prodrug thereof, and a composition comprising these compounds. The compounds provided can be used as inhibitors of MEK and are useful in the treatment of inflammatory diseases, cancer and other hyperproliferative diseases. The invention further provides a method of treatment for inflammatory diseases, cancer and other hyperproliferative diseases in mammals, especially humans
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Page/Page column 20
(2012/09/25)
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- TBD catalysis with dimethyl carbonate: A fruitful and sustainable alliance
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This work presents the synthesis of unsymmetric and symmetric organic carbonates as well as the synthesis of polycarbonates in an efficient and sustainable approach. All reactions were carried out at atmospheric pressure at 80°C and the use of classic toxic and harmful chemicals, such as phosgene and carbon monoxide, was avoided. The key finding of this manuscript is that the use of 1,5,7-triazabicyclo[4.4.0]dec-5-ene, TBD, an organocatalyst, in combination with dimethyl carbonate (DMC), a non-toxic and renewable starting material, allows the synthesis of the mentioned unsymmetric carbonates in yields of up to 98% under optimized conditions. The structure of the alcohols used for this approach was found to influence the DMC-ROH ratio required to maximize the yield of the desired structure. Finally, the results obtained for the synthesis of low molecular weight building blocks could be transferred to the catalytic synthesis of high molecular weight polycarbonates. The Royal Society of Chemistry.
- Mutlu, Hatice,Ruiz, Johal,Solleder, Susanne C.,Meier, Michael A. R.
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supporting information
p. 1728 - 1735
(2013/02/22)
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- Palladium-catalyzed synthesis of 2,3-dihydro-2-ylidene-1,4-benzodioxins
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Palladium-catalyzed condensation of benzene-1,2-diol with various propargylic carbonates, afforded regio- and stereoselectively 2,3-dihydro-2-ylidene-1,4-benzodioxins. The reaction is suggested to proceed by the formation of a (σ-allenyl)palladium complex, followed by the intermolecular attack of the phenoxide ion on this complex to generate a new (σ-allyl)palladium complex in equilibrium with the corresponding (η3-allyl)palladium complex. Intramolecular attack of the phenoxide ion afforded the corresponding benzodioxan compound. This last attack occurs predominantly at the more electrophilic end of the (η3-allyl)palladium intermediate. The Z- or E-stereochemistry of the products was established by 1H NMR and proton NOE measurements and also by X-ray analysis on an example. The Z-stereochemistry generally observed is in agreement with the formation of this (η3-allyl)palladium intermediate. However, in the case of tertiary propargylic carbonates, the E-stereochemistry generally observed could be explained by an intramolecular attack of the phenoxide ion on the intermediate (σ-allyl)palladium complex, in slow equilibrium with the (η3allyl)palladium complex.
- Labrosse,Lhoste,Sinou
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p. 6634 - 6642
(2007/10/03)
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- Synthesis of phenylthiomethyl substituted furans by Lewis acid catalysed substitution
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Two routes to the differentially functionalised trisubstituted furan methyl 4-methyl-2-[(phenylthio)methyl]-3-furoate are presented. One is a direct palladium catalysed annulation which proceeds smoothly in the presence of a thioether and the other depends on a highly chemoselective displacement of a methoxy group by phenylthiotrimethylsilane. The scope and mechanism of the latter transformation was probed with simple model systems.
- Greeves,Torode
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p. 1109 - 1112
(2007/10/02)
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- Intramolecular and intermolecular Diels-Alder reactions of acylhydrazones derived from methacrolein and ethylacrolein
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The intramolecular Diels-Alder reactions of hydrazones derived from methacrolein or ethylacrolein and terminally unsaturated N-acyl-N-methylhydrazines have been investigated. The hydrazones 7b and 7c derived from N-methyl-N-pent-4-enoylhydrazine 3b were found to undergo intramolecular [4 + 2] cycloaddition above 140°C and the pyridopyridazones 12 were isolated. The corresponding hydrazones 8b and 8c from N-methyl N-pent-4-ynoylhydrazone 4a reacted similarly and gave as the final products the pyridines 13. The scope of the reaction is limited, as was shown by the failure of several other terminally unsaturated hydrazones of αβ-unsaturated aldehydes to undergo intramolecular cycloaddition. These hydrazones did, however, undergo intermolecular [4 + 2] cycloaddition to N-phenylmaleimide. Other hydrazones 15 of methacrolein, including the benzoylhydrazone and the phenylhydrazone, also reacted with N-phenylmaleimide to give the pyridine 14b by way of an isolable dihydropyridine 16.
- Allcock,Gilchrist,Shuttleworth,King
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p. 10053 - 10064
(2007/10/02)
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