1523-89-3Relevant academic research and scientific papers
Tandem and One-Pot Hydroformylation/Michael Reactions of Acrylates
Quintero-Duque, Samuel,Fleischer, Ivana
, p. 925 - 932 (2017)
The combination of various reactions in one operational step leads to many advantages in synthetic strategies, such as a lower consumption of resources, effort, and time, when intermittent workup and purification steps can be avoided. The hydroformylation reaction of acrylates gives access to 2-formylpropanoates, which thanks to their structural features constitute useful intermediates in the synthesis of more complex compounds. Herein, we report a simple and convenient one-pot strategy to synthesize functionalized carbonyl compounds starting from these readily available substrates, via tandem or one-pot hydroformylation, Michael addition, and aldol reactions.
Synthesis, chemical reactivity as michael acceptors, and biological potency of monocyclic cyanoenones, novel and highly potent anti-inflammatory and cytoprotective agents(1)
Zheng, Suqing,Santosh Laxmi,David, Emilie,Dinkova-Kostova, Albena T.,Shiavoni, Katherine H.,Ren, Yanqing,Zheng, Ying,Trevino, Isaac,Bumeister, Ronald,Ojima, Iwao,Wigley, W. Christian,Bliska, James B.,Mierke, Dale F.,Honda, Tadashi
, p. 4837 - 4846 (2012/07/03)
Novel monocyclic cyanoenones examined to date display unique features regarding chemical reactivity as Michael acceptors and biological potency. Remarkably, in some biological assays, the simple structure is more potent than pentacyclic triterpenoids (e.g
Scalable synthesis of highly reactive 1,3-diamino dienes from vinamidinium salts and their use in Diels-Alder reactions
Zhou, Sida,Sanchez-Larios, Eduardo,Gravel, Michel
experimental part, p. 3576 - 3582 (2012/06/15)
A practical and chromatography-free synthesis of vinamidinium salts and their use as diene precursors in Diels-Alder reactions is reported. Additionally, 1,3-dipyrrolidino-1,3-butadiene was shown to be significantly more reactive than Rawal's diene in a c
COMPOUNDS INCLUDING AN ANTI-INFLAMMATORY PHARMACORE AND METHODS OF USE
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Page/Page column 123, (2009/12/27)
This invention provides novel compounds comprising the following anti-inflammatory pharmacore Formula (I): wherein X, R1 and R2 are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds, methods and intermediates useful for making the compounds, and methods of using the compounds and compositions.
The Diels-Alder Route to Allylsilanes from 1-Trimethylsilylbutadienes
Carter, Martin J.,Fleming, Ian,Percival, Alan
, p. 2415 - 2434 (2007/10/02)
The synthesis and Diels-Alder reactions of 1-trimethylsilylbutadiene (3) and its 3-methyl (17), 3-trimethylsilyloxy (20), 4-methyl (4), and 4-trimethylsilyl (6) derivatives are reported.The silyl group reduces somewhat the rate of the Diels-Alder reactions, and has, if anything, a small 'ortho'-directing effect on the regioselectivity in the reactions of (3) with methyl acylate, methyl propiolate, citraconic anhydride, and 2,6-dimethylbenzoquinone.The other substituent in the dienes (17), (20), and (4) is therefore the major influence on the regioselectivity in the reactions of these dienes with methyl acrylate and methyl propiolate.The products of the Diels-Alder reactions of (3), (17), and (4) are allylsilanes, which undergo clean protodesilylation with acid, and, with the acid and ester derived from the maleic anhydride adduct of (3), undergo epoxidation and sulphenylation reactions giving an allyl alcohol (33) and an allyl sulphide (37), respectively.The adducts from (20) can be hydrolysed to β-silylketones, which can be converted into enones by bromination. 1-Pentamethyldisilylbutadiene (15) is no more reactive and no more regioselective than (3).The 'ortho'-adduct (42) from the reaction of (3) and methyl propiolate aromatises with DDQ to give methyl m-trimethylsilylbenzoate (53) in high yield, in a reaction involving rearrangement of the silyl group, even though a direct dehydrogenation is an available pathway.
