36044-49-2Relevant academic research and scientific papers
A new approach to the synthesis of chromene derivatives
Ravichandran
, p. 1233 - 1235 (2001)
3-Acetyl-5,6-benzopyran and 3-benzoyl-5,6-benzopyran have been simply prepared by condensation of methylvinyl ketone and phenylvinyl ketone with salicylaldehyde in an aqueous DABCO medium at room temperature.
Systematic methodology for the development of biocatalytic hydrogen-borrowing cascades: Application to the synthesis of chiral α-substituted carboxylic acids from α-substituted α,β-unsaturated aldehydes
Knaus, Tanja,Mutti, Francesco G.,Humphreys, Luke D.,Turner, Nicholas J.,Scrutton, Nigel S.
supporting information, p. 223 - 233 (2015/02/19)
Ene-reductases (ERs) are flavin dependent enzymes that catalyze the asymmetric reduction of activated carbon-carbon double bonds. In particular, α,β-unsaturated carbonyl compounds (e.g. enals and enones) as well as nitroalkenes are rapidly reduced. Conversely, α,β-unsaturated esters are poorly accepted substrates whereas free carboxylic acids are not converted at all. The only exceptions are α,β-unsaturated diacids, diesters as well as esters bearing an electron-withdrawing group in α- or β-position. Here, we present an alternative approach that has a general applicability for directly obtaining diverse chiral α-substituted carboxylic acids. This approach combines two enzyme classes, namely ERs and aldehyde dehydrogenases (Ald-DHs), in a concurrent reductive-oxidative biocatalytic cascade. This strategy has several advantages as the starting material is an α-substituted α,β-unsaturated aldehyde, a class of compounds extremely reactive for the reduction of the alkene moiety. Furthermore no external hydride source from a sacrificial substrate (e.g. glucose, formate) is required since the hydride for the first reductive step is liberated in the second oxidative step. Such a process is defined as a hydrogen-borrowing cascade. This methodology has wide applicability as it was successfully applied to the synthesis of chiral substituted hydrocinnamic acids, aliphatic acids, heterocycles and even acetylated amino acids with elevated yield, chemo- and stereo-selectivity. A systematic methodology for optimizing the hydrogen-borrowing two-enzyme synthesis of α-chiral substituted carboxylic acids was developed. This systematic methodology has general applicability for the development of diverse hydrogen-borrowing processes that possess the highest atom efficiency and the lowest environmental impact. This journal is
Compounds that modulate PPAR activity and methods of preparation
-
, (2008/06/13)
This invention discloses compounds that alter PPAR activity. The invention also discloses pharmaceutically acceptable salts of the compounds, pharmaceutically acceptable compositions comprising the compounds or their salts, and methods of using them as therapeutic agents for treating or preventing hyperlipidemia and hypercholesteremia in a mammal. The present invention also discloses method for making the disclosed compounds.
Does the DABCO-catalysed reaction of 2-hydroxybenzaldehydes with methyl acrylate follow a Baylis-Hillman pathway?
Kaye, Perry T.,Musa, Musiliyu A.,Nocanda, Xolani W.,Robinson, Ross S.
, p. 1133 - 1138 (2007/10/03)
Evidence is presented which supports the intermediacy of dipolar Baylis-Hillman-type adducts in the synthesis of coumarin and chromene derivatives from the reaction of 2-hydroxybenzaldehydes with methyl acrylate in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO).
Novel products from Baylis-Hillman reactions of salicylaldehydes
Bacsa, John,Kaye, Perry T.,Robinson, Ross S.
, p. 47 - 54 (2007/10/03)
High resolution NMR spectroscopy and X-ray crystallography have been used to identify some unusual chrornene and coumarin derivatives isolated from DABCO-catalysed reactions of substituted salicylaldehydes with methyl acrylate.
Dabco-catalysed reactions of salicylaldehydes with acrylate derivatives
Kaye, Perry T.,Robinson, Ross S.
, p. 2085 - 2097 (2007/10/03)
Treatment of salicylaldehydes with acrylate derivatives in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) has been shown to afford both coumarin and chromene derivatives, and factors influencing the product distributions have been investigated.
STUDIES ON THE SEQUENTIAL CLAISEN REARRANGEMENT OF METHYL-3-ARYLOXY-2-(ARYLOXYMETHYL)PROP-2-ENOATES
Gopal, D.,Rajagopalan, K.
, p. 5327 - 5330 (2007/10/02)
Claisen rearrangement of methyl-3-aryloxy-2-(aryloxymethyl)prop-2-enoates (4) in refluxing N,N-diethylaniline gave 3-(2-hydroxyphenylmethylene)-3,4-dihydro-2H-1-benzopyran-2-ones (6) and 3-methoxycarbonyl-2H-1-benzopyrans (7).
