- Morita-Baylis-Hillman reaction in eutectic solvent under aqueous medium
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A series of deep eutectic solvents (DESs) based on choline chloride were prepared and used in the Morita-Baylis-Hillman (M-B-H) reaction. Research showed that the composite solvent (1ChCl/2Gly DES-H2O) is a very effective solvent media for all
- Zhao, Sanhu,Zhi, Hangyu,Zhang, Mi,Yan, Qin,Fan, Jianfeng,Guo, Jinchang
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p. 62778 - 62784
(2016/07/15)
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- Cl-H2O: An efficient and versatile solvent system for the DABCO-catalyzed Morita-Baylis-Hillman reaction
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An efficient and versatile solvent-catalyst system, [HyEtPy]Cl-H2O-DABCO, has been developed and used in the Morita-Baylis-Hillman reaction. Under the mild reaction conditions, Morita-Baylis-Hillman proceeds very quickly and efficiently. This protocol has notable advantages such as eco-friendliness, ease of work-up and reuse of ionic liquid conveniently, which could help reduce disposal costs and contribute to the development of a new solvent-catalyst system for use in green and continuous chemical processes.
- Zhao, Sanhu,He, Meiyan,Guo, Zhaonan,Zhou, Na,Wang, Dou,Li, Jinlong,Zhang, Liwei
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p. 32839 - 32845
(2015/04/27)
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- Selective hydrogenation of indolizines: An expeditious approach to derive tetrahydroindolizines and indolizidines from Morita-Baylis-Hillman adducts
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In this study, we describe the hydrogenation of indolizines derived from Morita-Baylis-Hillman adducts. We demonstrate that functionalized tetrahydroindolizines and indolizidines can be prepared selectively, at low pressure, by simply adjusting the acidity of the medium. Using this simple and straightforward strategy, substituted tetrahydroindolizines and indolizidines were obtained diastereoselectively in high yield.
- Teodoro, Bruno V. M.,Correia, José Tiago M.,Coelho, Fernando
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p. 2529 - 2538
(2015/03/18)
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- INDOLIZINE DERIVATIVES AS PHOSHOINOSITIDE 3-KINASES INHIBITORS
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Compounds of formula (I), defined herein, inhibit phosphoinositide 3-kinases (PI3K) and are useful for the treatment of disorders associated with PI3K enzymes.
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Paragraph 0279; 0280
(2015/12/31)
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- Electrophilic warhead-based design of compounds preventing NLRP3 inflammasome-dependent pyroptosis
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Pyroptosis is a caspase-1-dependent pro-inflammatory form of programmed cell death implicated in the pathogenesis of autoinflammatory diseases as well as in disorders characterized by excessive cell death and inflammation. Activation of NLRP3 inflammasome
- Cocco, Mattia,Garella, Davide,Di Stilo, Antonella,Borretto, Emily,Stevanato, Livio,Giorgis, Marta,Marini, Elisabetta,Fantozzi, Roberto,Miglio, Gianluca,Bertinaria, Massimo
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p. 10366 - 10382
(2015/02/19)
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- Microwave-assisted convenient syntheses of 2-indolizine derivatives from Morita-Baylis-Hillman adducts: New in silico potential ion channel modulators
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In this work, a microwave-assisted synthesis study by microwave irradiation to produce indolizine-2-carbonitrile and indolizine-2-carboxylate in good to high yields (70 and 81percent, respectively) in one step from Morita-Baylis-Hillman adducts (MBHA) is presented. These compounds were subsequently transformed to high yields (94 to 100percent, respectively) in three 2-indolizine derivatives. The five synthesized compounds were designed in silico aiming to present potential selective activities as ion channel modulators. These activities were suggested by the score values using Molinspiration Cheminformatics program.
- Cunha, Saraghina M.D.,De Oliveira, Ramon G.,Vasconcellos, Ma?rio L.A.A.
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p. 432 - 438
(2013/08/25)
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- Antimitotic activity on sea urchin embryonic cells of seven antiparasitic morita-baylis-hillman adducts: A potential new class of anticancer drugs
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In the present work we described improvements in the 1-7 antiparasitic Morita-Baylis-Hillman Adducts synthesis and their antimitotic activity on sea urchin embryonic cells. The 2-[Hydroxy(2-nitrophenyl)methyl]acrylonitrile (1) and 2-[Hydroxy(4-bromophenyl
- Leite, Jocelmo C. A.,Marques-Santos, Luis F.,Claudio Jr., G. L.,Silva, Fabio P. L.,Sousa, Suervy C. O.,Vasconcellos, Mario L. A. A.
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p. 1003 - 1011,9
(2012/12/12)
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- Highly efficient synthesis of novel Morita-Baylis-Hillman adducts from activated ketones using a DABCO-based hydroxy ionic liquid (HIL) as a recyclable catalyst-solvent
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A highly efficient non-imidazolium DABCO-based ionic liquid has been prepared for the synthesis of biologically active Morita-Baylis-Hillman adducts from activated ketones. The results show that the ionic liquid is very efficient in the Morita-Baylis-Hill
- Khalafi-Nezhad, Ali,Mohammadi, Somayeh
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experimental part
p. 1725 - 1735
(2012/07/01)
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- Microwave irradiation or low temperature improved synthesis of antiparasitic morita-baylis-hillman adducts
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It is reported the synthesis of 24 Morita-Baylis-Hillman adducts (3a-3l/6a-6l) using microwave irradiation at 80 °C or conventional protocol at 0 °C to promote the reactions between aromatic aldehydes and methyl acrylate or acrylonitrile (81-99%). It is shown that the reaction of 2-hydroxy(4-bromophenyl)methyl acrylate formation is reversible at 120 °C.
- Claudio Jr.,Silva, Fabio P.L.,De Oliveira, Ramon G.,Subrinho, Fernanda L.,De Andrade, Natalia G.,Vasconcellos, Mario L.A.A.
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scheme or table
p. 2220 - 2224
(2012/02/03)
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- Efficient synthesis of 16 aromatic Morita-Baylis-Hillman adducts: Biological evaluation on Leishmania amazonensis and Leishmania chagasi
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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
- 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.
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experimental part
p. 279 - 284
(2011/02/22)
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- Baylis-Hillman reaction under solvent-free conditions - Remarkable rate acceleration and yield enhancement
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A simple and efficient method has been developed for remarkable rate acceleration and yield enhancement of the Baylis-Hillman reaction under solvent-free "neat conditions" and solvent-less isolation of products. Reaction of equimolar quantities of aldehyd
- Saikia, Monmi,Sarma, Jadab C.
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experimental part
p. 1271 - 1276
(2011/02/24)
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- Improved synthesis of seven aromatic Baylis-Hillman adducts (BHA): Evaluation against Artemia salina Leach. and Leishmania chagasi
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We described a very efficient procedure to prepare seven aromatic compounds (1-7), a new class of antileishmanial substances, through Baylis-Hillman reaction (BHR). With one, all the Baylis-Hillman adducts were prepared in quantitative yields by reaction
- Barbosa, Ticiano P.,Junior, Claudio G.L.,Silva, Fabio P.L.,Lopes, Horacimone M.,Figueiredo, Lucas R.F.,Sousa, Suervy C.O.,Batista, Guilherme N.,da Silva, Thiago G.,Silva, Tania M.S.,de Oliveira, Marcia R.,Vasconcellos, Mario L.A.A.
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experimental part
p. 1726 - 1730
(2009/05/27)
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- Magnetic nanoparticle-supported Morita-Baylis-Hillman catalysts
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A magnetic nanoparticle-supported quinuclidine was prepared and evaluated as a recoverable Morita-Baylis-Hillman catalyst. The supported catalyst 2 demonstrated comparable activity with that of DABCO and could be simply recycled with the assistance of an
- Luo, Sanzhong,Zheng, Xiaoxi,Xu, Hui,Mi, Xueling,Zhang, Long,Cheng, Jin-Pei
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p. 2431 - 2434
(2008/09/19)
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- 1,3,5-triaza-7-phosphaadamantane (PTA): A practical and versatile nucleophilic phosphine organocatalyst
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In this paper, the air-stable and readily available 1,3,5-triaza-7- phosphaadmantane (PTA) is reported as a practical and versatile nucleophilic phosphine organocatalyst. Under the mediation of 15-30 mol% of PTA, various electrophiles like aldehydes and i
- Tang, Xiaofang,Zhang, Bo,He, Zhengrong,Gao, Ruili,He, Zhengjie
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p. 2007 - 2017
(2008/09/18)
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- Hydroxyl ionic liquid (HIL)-immobilized quinuclidine for Baylis-Hillman catalysis: Synergistic effect of ionic liquids as organocatalyst supports
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Hydroxyl ionic liquid (HIL) has been explored as a novel support for Baylis-Hillman catalyst. The HIL-supported catalyst showed a better catalytic activity compared to other IL-immobilized catalyst that has no hydroxyl group attached to the IL scaffold. T
- Mi, Xueling,Luo, Sanzhong,Xu, Hui,Zhang, Long,Cheng, Jin-Pei
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p. 2537 - 2544
(2007/10/03)
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- Ionic liquid-immobilized quinuclidine-catalyzed Morita-Baylis-Hillman reactions
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(Chemical Equation Presented) The ionic liquid-bound quinuclidine catalyzed Baylis-Hillman reactions were investigated. The IL-supported catalyst showed equally good catalytic activity as compared with its nonimmobilized counterpart. The corresponding Bay
- Mi, Xueling,Luo, Sanzhong,Cheng, Jin-Pei
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p. 2338 - 2341
(2007/10/03)
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- Hexamethylenetetramine as a cheap and convenient alternative catalyst in the Baylis-Hillman reaction: Synthesis of aromatic compounds with anti-malarial activity
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Hexamethylenetetramine (7, HMT) is a cheap alternative catalyst in the Baylis-Hillman reaction between aromatic aldehydes and methyl acrylate or acrylonitrile. The use of 0.1 equiv or 1.0 equiv of HMT proved to be an efficient catalyst for the preparation
- De Souza,Meireles, Bruno A.,Aguiar, Lucia C. S.,Vasconcellos
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p. 1595 - 1600
(2007/10/03)
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- Ultrasound in Baylis-Hillman reactions with aliphatic and aromatic aldehydes: Scope and limitations
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The utilization of ultrasound radiation in the Baylis-Hillman reaction with several aldehydes (aromatics and aliphatics) and different α,β-unsaturated reactants is described. For all aldehydes tested, the utilization of ultrasound sources augmented the reaction rate and the chemical yields. The use of ultrasound with two different catalysts (tri-n-butylphosphine and 1,4-diazabicyclo[2.2.2]octane [DABCO]) was also investigated. It was clearly demonstrated that DABCO is much more effective for catalyzing a Baylis-Hillman reaction under the influence of ultrasound than is tri-n-butylphosphine. No effect on reaction rate was observed when the concentration of DABCO was increased.
- Coelho, Fernando,Almeida, Wanda P.,Veronese, Demetrius,Mateus, Cristiano R.,Silva Lopes, Elizandra C.,Rossi, Rodrigo C.,Silveira, Gabriel P.C.,Pavam, César H.
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p. 7437 - 7447
(2007/10/03)
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- Indolizine Studies. Part 2. Synthesis and NMR Spectroscopic Analysis of 2-Substituted Indolizines
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Thermal cyclisation of 3-acetoxy-3-(2-pyridyl)-2-methylenepropionate esters and related compounds provides convenient access to 2-substituted indolizines.Detailed one- and two-dimensional NMR spectroscopic analysis of the title compounds has facilitated interpretation of their 1H and 13C NMR spectra.
- Bode, Moira L.,Kaye, Perry T.
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p. 1809 - 1814
(2007/10/02)
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