159763-36-7Relevant academic research and scientific papers
Baylis-Hillman reactions in aqueous acidic media
Caumul, Prakashanand,Hailes, Helen C.
, p. 8125 - 8127 (2005)
The Baylis-Hillman reaction has been successfully performed under aqueous acidic conditions at pH 1, using a range of substrates and tertiary amines as catalysts.
Accelerating the optimization of enzyme-catalyzed synthesis conditionsviamachine learning and reactivity descriptors
Liang, Jinhu,Liu, Dongchang,Wan, Zhongyu,Wang, Quan-De
supporting information, p. 6267 - 6273 (2021/07/28)
Enzyme-catalyzed synthesis reactions are of crucial importance for a wide range of applications. An accurate and rapid selection of optimal synthesis conditions is crucial and challenging for both human knowledge and computer predictions. In this work, a
New allyldithiocarbimate salts: Synthesis, structure and antifungal activity
Albuini-Oliveira, Nathália M.,Alvarez, Natalia,Ellena, Javier,Guilardi, Silvana,Lima, Marcelo S.,Rubinger, Mayura M. M.,Souza, Rafael A. C.,Tavares, Eder C.,Vidigal, Antonio E. C.,Zacchi, Carlos H. C.,Zambolim, Laercio
, (2020/04/21)
Fifteen new allyldithiocarbimates were prepared from different allylic bromides and various potassium dithiocarbimates, yielding (Z)-2-(methoxycarbonyl)-3-(X-nitrophenyl)allyl-(N-R-sulfonyl)dithiocarbimates (where X = 2, 3 and 4; R = phenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl and 4-iodophenyl). These anions were isolated as tetraphenylphosphonium salts and characterized by HRMS, infrared, 1H and 13C NMR spectroscopies. Molecular electrostatic potentials were used to evaluate intermolecular interactions present in the new substances and to explain variations observed on their melting points. Single crystal X-ray diffraction experiments confirmed the Z stereochemistry of the allyldithiocarbimate anions. C–H?O, C–H?N, C–H?S and C–H?π intermolecular interactions in the solid state were studied by X-ray diffraction and Hirshfeld surface analyses. The new compounds inhibited the mycelial growth of various fungi species responsible for severe plant diseases. The allylithiocarbimates were especially active against Botrytis cinerea, with IC50 values as low as 20 μM, being more effective than the active principals of the commercial fungicides Ziram and Mancozeb.
Exploratory applications of 2-nitrobenzaldehyde-derived Morita–Baylis–Hillman adducts as synthons in the construction of drug-like scaffolds
Idahosa, Kenudi C.,Davies-Coleman, Michael T.,Kaye, Perry T.
, p. 417 - 430 (2019/01/24)
Morita–Baylis–Hillman adducts, prepared from 2-nitrobenzaldehyde precursors and either methyl acrylate or methyl vinyl ketone, have been used as critical synthons in the preparation of α-[(alkylamino)methyl]cinnamate esters and their but-3-en-2-one analogs, cinnamate ester-azidothymidine (AZT) conjugates, 2-quinolone and quinoline derivatives. Computer docking studies have been conducted to explore the potential of the cinnamate ester–AZT conjugates as potential dual-action HIV-1 integrase–reverse transcriptase (IN–RT) inhibitors. The results further demonstrate the applicability of Morita–Baylis–Hillman methodology in the construction of complex drug-like scaffolds.
SO2F2 mediated cascade dehydrogenative Morita-Baylis-Hillman reaction of the C(sp3)-H of primary alcohols with the C(sp2)-H of electron-deficient olefins for the assembly of allylic alcohols
Jiang, Ying,Alharbi, Njud S.,Sun, Bing,Qin, Hua-Li
, p. 29784 - 29787 (2019/10/02)
A cascade dehydrogenative Morita-Baylis-Hillman reaction of the C(sp3)-H of primary alcohols with the C(sp2)-H of electron-deficient olefins for forming allylic alcohols mediated by SO2F2 was developed. This method provides a mild process for the preparation of allylic alcohol moieties without the requirement of transition metals.
Organocatalyzed Decarboxylative Trichloromethylation of Morita–Baylis–Hillman Adducts in Batch and Continuous Flow
Enevoldsen, Martin V.,Overgaard, Jacob,Pedersen, Maja S.,Lindhardt, Anders T.
supporting information, p. 1204 - 1208 (2018/02/06)
Two protocols for the organocatalyzed decarboxylative trichloromethylation of Morita–Baylis–Hillman (MBH) substrates have been developed. Applying sodium trichloroacetate, as the trichloromethyl anion precursor, in combination with an organocatalyst and a
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 (2017/10/24)
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.
Stereoselective and regioselective synthesis of N-substituted methyl 2-((azolyl)methyl)-3-arylacrylates from Baylis–Hillman acetates
K?seceli ?zen?, Ay?en,?elik, Ilhami,K?kten, ?ule
, p. 323 - 334 (2017/07/04)
N -Substituted methyl 2-((azolyl)methyl)-3-arylacrylates were synthesized stereo- and regioselectively with one-pot reaction between Baylis–Hillman acetates and a suitable acylazole in the presence of K2 CO3 as a base catalyst. The t
Synthesis and in vitro anti Leishmania amazonensis biological screening of Morita-Baylis-Hillman adducts prepared from eugenol, thymol and carvacrol
Seixas Xavier, Francisco José,Da Franca Rodrigues, Klinger Antonio,De Oliveira, Ramon Guerra,Lima, Claudio Gabriel,Da Camara Rocha, Juliana,Keesen, Tatjana Souza Lima,De Oliveira, Marcia Rosa,Silva, Fábio Pedrosa Lins,De Almeida Vasconcellos, Mário Luiz Araújo
, (2016/12/03)
Leishmaniasis represents a series of severe neglected tropical diseases caused by protozoa of the genus Leishmania and is widely distributed around the world. Here, we present the syntheses of Morita-Baylis-Hillman adducts (MBHAs) prepared from eugenol, thymol and carvacrol, and their bioevaluation against promastigotes of Leishmania amazonensis. The new MBHAs are prepared in two steps from essential oils in moderate to good yields and present IC50 values in the range of 22.30-4.71 μM. Moreover, the selectivity index to the most potent compound is very high (SIrb > 84.92), far better than that of Glucantime (SIrb 1.39) and amphotericin B (SIrb = 22.34). Conformational analysis were carried out at the M062X//6-31+G(d,p) level of theory to corroborate a hypothesis about the nitroaromatic bioreduction mechanism.
Star-like polyionic heterogeneous nanocatalyst as a highly active catalyst for promotion of Baylis-Hillman reaction in [bmim]Cl
Valizadeh, Hassan,Shomali, Ashkan,Noorshargh, Saeideh
, p. 2169 - 2177 (2015/10/19)
The use of star-like polyionic Lewis base heterogeneous nanocatalyst for the Baylis-Hillman reaction of benzyl- and methylacrylates with aryl aldehydes has been investigated. The corresponding Baylis-Hillman adducts are obtained in good to high yields in
