114106-93-3Relevant articles and documents
Dramatic Rate Acceleration of the Baylis-Hillman Reaction in Homogeneous Medium in the Presence of Water
Cai, Juexiao,Zhou, Zhenghong,Zhao, Guofeng,Tang, Chuchi
, p. 4723 - 4725 (2002)
(Matrix Presented) In homogeneous H2O/solvent medium, the reaction rate of aromatic aldehydes and acrylonitrile or acrylate was greatly accelerated, which led to shorter reaction time, lower reaction temperature, and higher yield. In this react
Antiproliferative effect of?Baylis-Hillman adducts and?a?new phthalide derivative on?human tumor cell lines
Kohn, Luciana K.,Pavam,Veronese,Coelho,De Carvalho,Almeida, Wanda P.
, p. 738 - 744 (2006)
In this work we report our results concerning the study on the in vitro antiproliferative activity of 18 Baylis-Hillman adducts and some derivatives against a panel of humor tumor cell lines. A brief qualitative structure-activity relationship study indicated that carbon-carbon double bond and the presence of an electron-withdrawing substituent at the aromatic ring are essential for the activity. A quinoline-phthalide derivative has exhibited a potent effect on the proliferation of all cell lines. It is interesting to note their special cytotoxic activity against NCIADR cell line.
Efficient synthesis of 16 aromatic Morita-Baylis-Hillman adducts: Biological evaluation on Leishmania amazonensis and Leishmania chagasi
Junior, Claudio G.L.,De Assis, Priscila A.C.,Silva, Fabio P.L.,Sousa, Suervy C.O.,De Andrade, Natalia G.,Barbosa, Ticiano P.,Neris, Patricia L.N.,Segundo, Luiz V.G.,Anjos, Italo C.,Carvalho, Gabriel A.U.,Rocha, Gerd B.,Oliveira, Marcia R.,Vasconcellos, Mario L.A.A.
, p. 279 - 284 (2010)
Sixteen aromatic Morita-Baylis-Hillman adducts (MBHA) 1-16 were efficiently synthesized in a one step Morita-Baylis-Hillman reaction (MBHR) involving commercial aldehydes with methyl acrylate or acrylonitrile (81-100% yields) without the formation of side
On the tandem Morita-Baylis-Hillman/transesterification processes. Mechanistic insights for the role of protic solvents
Carpanez, Arthur G.,Coelho, Fernando,Amarante, Giovanni W.
, p. 83 - 91 (2018)
Despite the remarkable rate acceleration under protic solvents such as alcohols and water, the use of acrylates as activated alkenes places a problem due to the possibility of ester hydrolysis or transesterification. Therefore, the tandem transesterification/Morita-Baylis-Hillman (MBH) reactions were investigated by ESI(+)-MS/(MS) and 1H NMR techniques. For the first time, the MBH back-reaction was fully examined by ESI(+)-MS/(MS) using labelling reagents revealed the complex equilibrium involving the Michael-type addition step of DABCO to acrylate. C- and O-protonation were observed at this stage, showing the transesterification process occurs previous to the aldol step, which is the rate-determining step of the mechanism. At this stage, a short-lived tetrahedral intermediate might be involved and should be considered in these processes.
The Baylis-Hillman reaction in supercritical carbon dioxide: Enhanced reaction rates, unprecedented ether formation, and a novel phase-dependent 3-component coupling
Rose, Paul M.,Clifford, Anthony A.,Rayner, Christopher M.
, p. 968 - 969 (2002)
The Baylis-Hillman reaction can be efficiently carried out in scCO2 with enhanced reaction rates relative to comparable solution phase reactions; at low pressures, a novel dimerisation is observed which has led to the development of a novel one
1-Methylimidazole 3-N-oxide as a new promoter for the Morita-Baylis-Hillman reaction
Lin, Yu-Sheng,Liu, Chih-Wei,Tsai, Thomas Y. R.
, p. 1859 - 1861 (2005)
The Morita-Baylis-Hillman reaction of aldehydes with α,β- unsaturated ketones can be affected by the Lewis bases. We have found that 1-methylimidazole 3-N-oxide promoted the Morita-Baylis-Hillman reaction of various activated aldehyde compounds in non-sol
Antimalarial activity of 3-hydroxyalkyl-2-methylene- propionic acid derivatives
Kundu,Sundar,Kumar,Bhat,Biswas,Valecha
, p. 731 - 736 (1999)
Several Baylis-Hillman adducts and their derivatives were synthesized and evaluated as targeted potential anti-malarials. The compounds 4, 7 and 9 were found to have highest potency against P. falciparum in vitro. The in vivo test result of compound 4 and
The N,N,N′,N′-tetramethylethylenediamine mediated Baylis-Hillman reaction
Zhao, Sanhu,Chen, Zhaobin
, p. 121 - 127 (2005)
The Baylis-Hillman reaction of aromatic aldehydes with various activated alkenes catalyzed by N,N,N′,N′-Tetramethylethylenediamine (TMEDA) in aqueous medium were reported. The efficiency of this catalyst was examined in comparison with DABCO. It was demon
Study of the Baylis-Hillman reaction in a microreactor environment: First continuous production of Baylis-Hillman Adducts
Acke, Davy R. J.,Stevens, Christian V.
, p. 417 - 422 (2006)
The Baylis-Hillman reaction has been optimized for use under microreactor conditions. After optimization, the reaction could be performed continuously and approximately 30% faster compared to batch conditions, however at a quite low flow rate.
Superior amine catalysts for the Baylis-Hillman reaction: The use of DBU and its implications
Aggarwal, Varinder K.,Mereu, Andrea
, p. 2311 - 2312 (1999)
DBU, which is normally regarded as a hindered and non-nucleophilic base, is in fact the optimum catalyst for the Baylis-Hillman reaction, providing adducts at much faster rates than using DABCO or 3HQD; the scope of the Baylis-Hillman reaction is enhanced
