42768-88-7Relevant academic research and scientific papers
Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate
Coutant, Eloi P.,Hervin, Vincent,Gagnot, Glwadys,Ford, Candice,Baatallah, Racha,Janin, Yves L.
supporting information, p. 2853 - 2860 (2018/11/26)
We have explored here the scope of the age-old diethyl malonate-based accesses to α-amino esters involving Knoevenagel condensations of diethyl malonate on aldehydes, reductions of the resulting alkylidenemalonates, the preparation of the corresponding α-hydroxyimino esters and their final reduction. This synthetic pathway turned out to be general although some unexpected limitations were encountered. The synthetic modifications of some of the intermediates - using Suzuki-Miyaura coupling or cycloadditions - before undertaking the oximation step - provided accesses to further α-amino esters. Moreover, other pathways to α-hydroxyimino esters were explored including an attempt to improve the cycloadditions between ethyl β-bromo-α-hydroxyiminocarboxylate and various alkylfuranes.
Mechanistic studies and improvement of coinage metal-catalyzed transformation of alkynyloxiranes to furans: An alcohol addition-cyclization- elimination cascade
Blanc, Aurelien,Tenbrink, Katharina,Weibel, Jean-Marc,Pale, Patrick
supporting information; experimental part, p. 5342 - 5348 (2009/12/03)
(Chemical Equation Presented) In the presence of alcohol Ag or Au salts or complexes catalyze the conversion of alkynyloxiranes to substituted furans. Both catalysts are effective, and a large furan diversity can be obtained in high yield with one or the
Compounds, Compositions and methods for insect control
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Page/Page column 14, (2008/06/13)
Rapidly acting compositions having vapor phase insecticidal activity comprise natural products or natural product-based materials. Further, these materials are non-petroleum based, are typically 100% biodegradable, and typically do not persist in the environment, unlike traditional pesticides. The compositions kill susceptible insects on contact in seconds, even the notoriously hardy peripleneta species. The compositions also kill insects behind cracks and crevices and when sprayed onto absorbent surfaces such as wood and plasterboard, where traditional contact insecticides work poorly or not at all. New methods of testing insecticides can be used to quantify these effects.
An Expedient Route for the Stereoselective Construction of Bridged Polyheterocyclic Ring Systems Using the Tandem "Pincer" Diels-Alder Reaction
Lautens, Mark,Fillion, Eric
, p. 4418 - 4427 (2007/10/03)
The tandem "pincer" Diels-Alder reaction, consisting of two consecutive [4 + 2] cycloadditions between two dienes and an acetylenic bis-dienophile, has been applied toward the rapid construction of bridged polyoxacyclic ring systems when furan derivatives are used as the diene components. The study has demonstrated the stereoselectivity (exo-exo adduct), the chemoselectivity ("pincer" vs "domino"), as well as the regioselectivity of the reaction. The reaction has been successfully applied to a variety of 2-substituted furans and tethered bis-furans in combination with mono-activated and diactivated dienophiles. The synthesis of unsymmetrical cycloadducts starting from the aza- and oxanorbornadiene-type intermediate has also been realized.
Intermediates for making N-aryl and N-heteroarylamide and urea derivatives as inhibitors of acyl coenzyme A: cholesterol acyl transferase (ACAT)
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, (2008/06/13)
Compounds of the formula STR1 wherein R21 and R22 are as defined in the specification which are intermediates useful in the preparation of compounds of the formula STR2 and the pharmaceutically acceptable salts thereof, wherein Q and R1 are as defined in the specification. The compounds of formula I are inhibitors of acyl coenzyme A: cholesterol acyltransferase (ACAT) and are useful as hypolipidemic and antiatherosclerosis agents.
New N-aryl and N-heteroarylamide and urea derivatives as inhibitors of acyl coenzyme A: cholesterol acyl transferase
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, (2008/06/13)
Compounds of the formula the pharmaceutically acceptable salts thereof, wherein Q and R1 are as defined below, and novel carboxylic acid and acid halide intermediates used in the synthesis of such compounds. The compounds of formula I are inhibitors of acyl coenzyme A: cholesterol acyltransferase (ACAT) and are useful as hypolipidemic and antiatherosclerosis agents.
AN EFFICIENT STEREOSELECTIVE SYNTHESIS OF Z-2-(2-METHYLENE CYCLOHEXYLIDENE)ETHANOL BY THE PHOTOSENSITIZED OXYGENATION OF 1-VINYLCYCLOHEXENE. A MODEL FOR RING A OF CALCITRIOL
Ficini, Jacqueline,Barbara, Claude,Ouerfelli, Ouathek
, p. 547 - 551 (2007/10/02)
The reaction of singlet oxygen with the vinylcyclohexene leads to an endoperoxide which is a model for a possible route to ring A of calcitriol.
SYNTHESIS OF FURANS BY CARBENE INSERTION
Buxton, Sheila R.,Holm, Kjetil H.,Skattebol, Lars
, p. 2167 - 2168 (2007/10/02)
reactions of α,α-dimethoxy ketones with diethyl diazomethylphosphonate proceed initially to dihydrofurans, probably through C-H insertion of a carbene intermediate; subsequent elimination of methanol affords the corresponding furans in good overall yields
Photooxygenation of 1-Vinylcycloalkenes. The Competition between "Ene" Reaction and Cycloaddition of Singlet Oxygen
Herz, Werner,Juo, Rouh-Rong
, p. 618 - 627 (2007/10/02)
The competition between the "ene" reaction and 1,4-cycloaddition reaction of 1O2 in a series of 1-vinylcycloalkenes (n = 5-10, 12) and 1-isopropenylcycloalkenes (n = 6-8) was studied.Ring size had a profound effect.When n = 5 or 7, products of the "ene" reaction predominated, but as ring size increased cycloaddition competed closely with the "ene" process, the crossover being at ring size 10. 1-Vinylhexenes constituted an exception with 1,4-cycloaddition greatly predominant. "Ene" products were almost exclusively conjugated diene hydroperoxides or secondary products derived from them; small amounts of unconjugated diene hydroperoxides were formed only when n = 9, 10, or 12.The influence of ring size of the "ene" to cycloaddition product ratio is compared with the rates of photooxygenation and the degree of syn-regiospecificity exhibited by (Z)-1-methylcycloalkenes and attributed to the same mainly conformational factors, as is the geometry of the "ene" products.The 1,4-cycloaddition products were converted to furans by means of ferrous sulfate.
