18020-59-2Relevant academic research and scientific papers
Acceleration of the Baylis-Hillman reaction in the presence of ionic liquids
Kim, Eun Jin,Ko, Soo Y.,Song, Choong Eui
, p. 894 - 899 (2003)
The Baylis-Hillman reaction is accelerated in the presence of ionic liquids. Of various 1-butyl-3-methylimidazolium (bmim)-based ionic liquids tested, [bmim][PF6] has been found to result in the highest rate increase. In the company of Lewis ac
Salt effects on the Baylis-Hillman reaction
Kumar, Anil,Pawar, Sanjay S.
, p. 5019 - 5026 (2003)
The Baylis-Hillman reaction is shown to accelerate in salt solutions of water and the 'water-like' structured solvents, like formamide and N-methylformamide in the presence of DABCO. Ethylene glycol, another structured solvent and its salt solutions fail
Studies on Pumiliotoxin A Alkaloids: An Approach to Preparing the Indolizidinic Core by Intramolecular Diastereoselective N-Heterocyclic Carbene Catalyzed Benzoin Reaction
Correia, José Tiago M.,Acconcia, Laís V.,Coelho, Fernando
, p. 1972 - 1976 (2016)
In this article, we describe the development of a convergent organocatalytic strategy to prepare the indolizidinic core of the pumiliotoxin A alkaloid family. The key step of the proposed strategy is based on a diastereoselective N-heterocyclic carbene ca
Selenonium ionic liquid as efficient catalyst for the Baylis-Hillman reaction
Lenard?o, Eder J.,Feijó, Josiane de Oliveira,Thurow, Samuel,Perin, Gelson,Jacob, Raquel G.,Silveira, Claudio C.
, p. 5215 - 5217 (2009)
The new acidic ionic liquid phenyl butyl ethyl selenonium tetrafluoroborate, [pbeSe]BF4, was successful used as a co-catalyst in the Baylis-Hillman reaction of aldehydes and electron-deficient alkenes. The Baylis-Hillman adducts were obtained i
Kinetic and mechanistic investigations of the Baylis-Hillman reaction in ionic liquids
Singh, Anshu,Kumar, Anil
, p. 2994 - 3004 (2015)
We report here a quantitative study of the kinetics and mechanism of the Baylis-Hillman reaction in the presence of ionic liquids as solvent media. Apparently, a simple Baylis-Hillman reaction can occur by two different exclusive mechanisms in ionic liquids. The delicate balance of these mechanisms is maintained by the ionic environment employed. The main features of the possible mechanism have been described here along with interesting kinetic consequences. The measurement of rate constants and activation energy parameters demonstrate that as the medium becomes basic, the order of the reaction changes from 1 to 2. An unexpected change in the mechanism of the reaction is observed with a change in the nature of the ionic liquid. The Linear Solvation Energy Relationship has also been used as an investigating tool to delineate the respective contributions of the cation and anion of the ionic liquid. The observation strongly dictates the dependency of the mechanism of the Baylis-Hillman reaction on the nature of the anion of the ionic liquids undertaken for this study.
An Improved Protocol for the Morita-Baylis-Hillman Reaction Allows Unprecedented Broad Synthetic Scope
Amarante, Giovanni W.,Camilo, Nilton S.,Carpanez, Arthur G.,Coelho, Fernando,Fernandes, Fábio S.,Lima, Samia R.,Rodrigues, Manoel T.,Santos, Hugo,Serafim, José Cláudio,Silva, Thiago S.,Zeoly, Lucas A.,de Oliveira, Aline S. B.
supporting information, (2022/01/22)
The Morita-Baylis-Hillman (MBH) reaction has been stablished as an important C?C bond-forming transformation between carbonyl-containing compounds and activated olefins. However, the slow reaction rate usually observed with electron-rich electrophilic par
β,γ-Diaryl α-methylene-γ-butyrolactones as potent antibacterials against methicillin-resistant Staphylococcus aureus
Abutaleb, Nader S.,Hamann, Henry J.,Pal, Rusha,Ramachandran, P. Veeraraghavan,Seleem, Mohamed N.
supporting information, (2020/10/02)
A selected series of racemic α-methylene-γ-butyrolactones (AMGBL) synthesized via allylboration or allylindation reactions were screened against methicillin-resistant Staphylococcus aureus (MRSA) USA300. Unlike natural AMGBLs, such as parthenolide, synthe
Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-Triazoles and regiospecific access to bromomethylcoumarins from Morita-Baylis-Hillman adducts
Karthikeyan, Soundararajan,Shobana, Radha Krishnan,Subimol, Kamarajapurathu Raju,Helen Ratna Monica,Kumar, Ayyanoth Karthik Krishna
, p. 1579 - 1587 (2020/09/16)
The direct transformation of Morita-Baylis-Hillman (MBH) adducts into molecules of interest is a crucial process wherein allylic hydroxy-protected or halogenated MBH adducts are commonly preferred. Herein, we report an azidophosphonium salt (AzPS)-catalys
Spirocyclohexadienones as an uncommon scaffold for acetylcholinesterase inhibitory activity
Almeida, Wanda P.,Coelho, Fernando,Gomes, Ralph C.,Sakata, Renata P.
, p. 373 - 382 (2019/07/12)
Background: The most important cause of dementia affecting elderly people is the Alzheimer’s disease (AD). Patients affected by this progressive and neurodegenerative disease have severe memory and cognitive function impairments. Some medicines used for t
Iron(III) Chloride/Phenylsilane-Mediated Cascade Reaction of Allyl Alcohols with Maleimides: Synthesis of Poly-Substituted γ-Butyrolactones
Zhang, Hua,Zhan, Xiao-Yu,Chen, Xu-Ling,Tang, Lei,He, Shuai,Shi, Zhi-Chuan,Wang, Yu,Wang, Ji-Yu
supporting information, p. 4919 - 4925 (2019/11/03)
A iron-catalyzed free radical cascade reaction of allyl alcohols with N-substituted maleimides for accessing poly-substituted γ-butyrolactones has been developed. In this protocol, various allyl alcohols can open N-substituted maleimide rings to form allyl ester intermediates, and the allyl ester intermediates can be converted into an allyl ester alkyl radicals and undergo intramolecular free radical addition cyclization to form a polysubstituted γ-butyrolactones. In this protocol, spiro γ-butyrolactone compounds can be also synthesized. Meanwhile, the strategy could be applied to further construct a fully substituted tetrahydrofuran. The reaction is not sensitive to oxygen or moisture and has been performed on gram-scale. (Figure presented.).
