53366-79-3Relevant academic research and scientific papers
Irreversible endo-Selective Diels-Alder Reactions of Substituted Alkoxyfurans: A General Synthesis of endo-Cantharimides
Foster, Robert W.,Benhamou, Laure,Porter, Michael J.,Bu?ar, Dejan-Kre?imir,Hailes, Helen C.,Tame, Christopher J.,Sheppard, Tom D.
, p. 6107 - 6114 (2015)
The [4+2] cycloaddition of 3-alkoxyfurans with N-substituted maleimides provides the first general route for preparing endo-cantharimides. Unlike the corresponding reaction with 3H furans, the reaction can tolerate a broad range of 2-substitued furans including alkyl, aromatic, and heteroaromatic groups. The cycloaddition products were converted into a range of cantharimide products with promising lead-like properties for medicinal chemistry programs. Furthermore, the electron-rich furans are shown to react with a variety of alternative dienophiles to generate 7-oxabicyclo[2.2.1]heptane derivatives under mild conditions. DFT calculations have been performed to rationalize the activation effect of the 3-alkoxy group on a furan Diels-Alder reaction.
Gold catalysed synthesis of 3-alkoxyfurans at room temperature
Pennell, Matthew N.,Foster, Robert W.,Turner, Peter G.,Hailes, Helen C.,Tame, Christopher J.,Sheppard, Tom D.
supporting information, p. 1302 - 1304 (2014/01/23)
Synthetically important 3-alkoxyfurans can be prepared efficiently via treatment of acetal-containing propargylic alcohols (obtained from the addition of 3,3-diethoxypropyne to aldehydes) with 2 mol% gold catalyst in an alcohol solvent at room temperature. The resulting furans show useful reactivity in a variety of subsequent transformations. The Royal Society of Chemistry.
THIAZOLE AND THIOPHENE COMPOUNDS
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Page/Page column 38, (2012/09/25)
Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of inflammatory diseases and disorders such as, for example, asthma and COPD
Kinetic resolution of homoaldols via catalytic asymmetric transacetalization
Coric, Ilija,Mueller, Steffen,List, Benjamin
supporting information; experimental part, p. 17370 - 17373 (2011/02/23)
The highly enantioselective kinetic resolution of homoaldols via a transacetalization reaction has been achieved. A novel phosphoric acid, STRIP, based on a spirocyclic 1,1′-spirobiindane backbone was designed and identified as a superior catalyst for this transformation. Remarkably, both secondary and tertiary homoaldols gave equally excellent results.
53. Acid-Catalyzed Cyclization Rections of Substituted Acetylenic Ketones: A New Approach for the Synthesis of 3-Halofurans, Flavones, and Styrylchromones
Obrecht, Daniel
, p. 447 - 456 (2007/10/02)
Acetylenic acetals of type I (Scheme 1) and acetylenic ketones of type III (Scheme 1), 37 and 38 (Scheme 7) are versatile synthetic precursors for the synthesis of various heterocycles by acid-catalyzed cyclization reactions.By this way, substituted 3-halofurans of type II and IV (Scheme 1) and flavones and styrylchromones (Scheme 7) can be synthesized in good-to-excellent yields.The high degree of regioselectivity in the synthesis of the 3-halofurans (Scheme 4) is the result of the regioselective β-addition of HX (X = Cl, Br, I) to the acetylenic aldehyde and acetylenic ketone moieties.A possible mechanism is depicted in Scheme 5.Since 3-halofurans can easily be metalated and substituted, this approach constitutes a new synthesis of highly substituted furans.
