- Studying the Morita-Baylis-Hillman Reaction in Continuous Flow Using Packed Bed Reactors
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Conditions for the Morita-Baylis-Hillman reaction were developed under continuous flow using a packed bed reactor carrying 4-(dimethylamino)pyridine immobilized on silica. High reaction rates were obtained, as the packed bed reactor mimics super-stoichiom
- Verdier, Rasmus A. T.,Mikkelsen, Jesper H.,Lindhardt, Anders T.
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- Phosphine-Catalyzed [3 + 2] Annulation of Morita-Baylis-Hillman Carbonates with Isoxazole-Based Alkenes
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A phosphine-catalyzed [3 + 2] annulation of Morita-Baylis-Hillman (MBH) carbonates with 3-methyl-4-nitro-5-styrylisoxazoles has been developed to afford various multifunctional isoxazoles in moderate to good yields with moderate to excellent diastereoselectivities. With a spirocyclic chiral phosphine as the catalyst, up to 89% ee was obtained.
- Liao, Jianning,Dong, Jipan,Xu, Jiaqing,Wang, Wei,Wu, Yongjun,Hou, Yuxia,Guo, Hongchao
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p. 2090 - 2099
(2021/02/05)
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- Phosphine-catalyzed [3+2] cycloaddition of Morita—Baylis—Hillman carbonates to isothiocyanates in the synthesis of adamantane-containing trisubstituted aminothiophenes
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An addition of the Morita—Baylis—Hillman (MBH) carbonates to adamantane-containing isothiocyanates was studied. The MBH carbonates react with 1-(4-isothiocyanatophenyl)-adamantane in the presence of triphenylphosphine to give 5-aryl-substituted adamantane
- Abel, A. S.,Averin, A. D.,Beletskaya, I. P.,Butov, G. M.,Zenkov, I. S.
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p. 880 - 884
(2021/06/07)
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- Synthesis of β-Lactams via Enantioselective Allylation of Anilines with Morita-Baylis-Hillman Carbonates
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Enantioenriched β-lactams are accessed via enantioselective allylation of anilines with Morita-Baylis-Hillman carbonates followed by a base-promoted cyclization. The resulting 3-methyleneazetidin-2-ones are amenable to diastereoselective functionalization
- Krieck, Sven,Lange, Markus,Schüler, Philipp,Vilotijevic, Ivan,Westerhausen, Matthias,Zi, You
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p. 575 - 580
(2020/03/27)
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- Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-Triazoles and regiospecific access to bromomethylcoumarins from Morita-Baylis-Hillman adducts
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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
- Karthikeyan, Soundararajan,Shobana, Radha Krishnan,Subimol, Kamarajapurathu Raju,Helen Ratna Monica,Kumar, Ayyanoth Karthik Krishna
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p. 1579 - 1587
(2020/09/16)
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- Direct Synthesis of Dihydropyrrolo[2,1-a]Isoquinolines through FeCl3 Promoted Oxidative Aromatization
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We have developed a straightforward FeCl3 promoted synthesis of dihydropyrrolo[2,1-a]isoquinolines through formal (3+2) cycloaddition/oxidative aromatization cascade of dihydroisoquinoline with Morita-Baylis-Hillman carbonates (up to 96% yield)
- Cui, Hai-Lei,Jiang, Lu,Tan, Hao,Liu, Si
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p. 4772 - 4780
(2019/10/28)
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- 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
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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.
- Jiang, Ying,Alharbi, Njud S.,Sun, Bing,Qin, Hua-Li
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p. 29784 - 29787
(2019/10/02)
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- Regioselective dehydroxytrifluoromethylthiolation of allylic and propargylic alcohols with AgSCF3
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The reaction of easily available Morita–Baylis–Hillman (MBH) alcohols with AgSCF3 in the presence of n-Bu4NI and KI affords primary allylic SCF3 products in high yields and excellent regioselectivities. This regioselective dehydroxytrifluoromethylthiolation protocol could also be extended to propargylic alcohols for the preparation of the primary propargylic SCF3 products.
- Liu, Yin-Li,Xu, Xiu-Hua,Qing, Feng-Ling
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p. 953 - 956
(2019/03/07)
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- Latent Nucleophiles in Lewis Base Catalyzed Enantioselective N-Allylations of N-Heterocycles
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Latent nucleophiles are compounds that are themselves not nucleophilic but can produce a strong nucleophile when activated. Such nucleophiles can expand the scope of Lewis base catalyzed reactions. As a proof of concept, we report that N-silyl pyrroles, i
- Zi, You,Lange, Markus,Schultz, Constanze,Vilotijevic, Ivan
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p. 10727 - 10731
(2019/07/09)
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- Enantioselective dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita-Baylis-Hillman carbonates
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The phosphine-catalyzed asymmetric dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita-Baylis-Hillman (MBH) carbonates or allenoate was developed. The reaction with MBH carbonates resulted in a series of cyclopentabenzofurans containing three contiguous stereocenters with good to high yields, diastereoselectivities and enantioselectivities. The use of allenoate also gave the target product with moderate enantioselectivity.
- Yang, Xin-He,Li, Jian-Ping,Wang, Dong-Chao,Xie, Ming-Sheng,Qu, Gui-Rong,Guo, Hai-Ming
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p. 9144 - 9147
(2019/08/07)
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- A Hydrazine Insertion Route to N′-Alkyl Benzohydrazides by an Unexpected Carbon-Carbon Bond Cleavage
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A serendipitous carbon-carbon bond cleavage in the reaction of benzoyl acrylates, derived from Morita-Baylis-Hillman adducts, with hydrazines delivered new N′,N′-disubstituted benzohydrazides. The reaction features a regioselective formation of two carbon
- Jha, Ajit Kumar,Kumari, Rajkiran,Easwar, Srinivasan
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p. 8191 - 8195
(2019/10/16)
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- Copper-Catalyzed One-Pot Borylative Aldolisation β-Fluoride Elimination for the Formal Addition of Acrylates to Carbonyl Moieties
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Herein, we report the copper-catalyzed domino borylation/aldolisation of methyl 2-fluoroacrylate with carbonyl compounds followed by an elimination to give Morita–Baylis–Hillman (MBH) analogues. The optimal conditions described were shown to be compatible
- Rasson, Corentin,Stouse, Adrien,Boreux, Arnaud,Cirriez, Virginie,Riant, Olivier
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p. 9234 - 9237
(2018/06/04)
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- Organocatalyzed Decarboxylative Trichloromethylation of Morita–Baylis–Hillman Adducts in Batch and Continuous Flow
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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
- Enevoldsen, Martin V.,Overgaard, Jacob,Pedersen, Maja S.,Lindhardt, Anders T.
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supporting information
p. 1204 - 1208
(2018/02/06)
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- Structural exploration of cinnamate-based phosphonic acids as inhibitors of bacterial ureases
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The conjugated system of cinnamic acid, α-substituted with a phosphonoalkyl residue, was previously validated as a scaffold that provided one of the most potent organophosphorus inhibitors of bacterial urease. Following the idea of using Morita-Baylis-Hil
- Ntatsopoulos, Vassilis,Macegoniuk, Katarzyna,Mucha, Artur,Vassiliou, Stamatia,Berlicki, ?ukasz
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supporting information
p. 307 - 316
(2018/10/15)
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- α-ZrP/Uracil/Cu2+ nanoparticles as an efficient catalyst in the Morita-Baylis-Hillman reaction
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A facile synthesis of uracil-Cu2+ nanoparticles immobilized on alpha-zirconium hydrogen phosphate (α-ZrP), abbreviated as α-ZrP/Uracil/Cu2+, was presented. This compound was synthesized by the thermal method and used as a reusable ca
- Hajipour, Abdol R.,Zakery, Saedeh
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- Decarboxylative Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbamates
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The present study reports the organocatalytic enantioselective allylic amination of Morita–Baylis–Hillman carbamates efficiently catalyzed by a chiral amine in the presence of a Br?nsted acid. Chiral allylic amines were produced in high yields (up to 98 %) and enantioselectivities (up to 97 % ee). This method provides an efficient and easily performed route to prepare α-methylene-β-lactams, and other optically active β-lactams, such as the cholesterol-lowering drug Ezetimibe.
- Do?ekal, Vojtěch,?imek, Michal,Dra?ínsky, Martin,Vesely, Jan
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p. 13441 - 13445
(2018/09/21)
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- Effective and diastereoselective preparation of dispiro[cyclopent-3′-ene]bisoxindoles: Via novel [3 + 2] annulation of isoindigos and MBH carbonates
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A novel and diastereoselective [3 + 2] annulation of isoindigos and Morita-Baylis-Hillman carbonates has been developed for the highly efficient and one-step preparation of highly steric dispiro[cyclopent-3′-ene]bisoxindoles with two all-carbon quaternary
- Ren, Hong-Xia,Peng, Lin,Song, Xiang-Jia,Liao, Li-Guo,Zou, Ying,Tian, Fang,Wang, Li-Xin
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p. 1297 - 1304
(2018/03/06)
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- Ir-Catalyzed Asymmetric Hydrogenation of α-Alkylidene β-Lactams and Cyclobutanones
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Chiral β-lactams and cyclobutanones are present in numerous natural and pharmaceutical products. The stereoselective construction of chiral four-membered cyclic compounds is an ongoing challenge for the chemical community. Herein, we report a highly stere
- Xia, Jingzhao,Nie, Yu,Yang, Guoqiang,Liu, Yangang,Gridnev, Ilya D.,Zhang, Wanbin
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p. 612 - 618
(2018/06/22)
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- Umpolung of o-Hydroxyaryl Azomethine Ylides: Entry to Functionalized ?-Aminobutyric Acid under Phosphine Catalysis
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A phosphine-catalyzed reaction between o-hydroxyaryl azomethine ylides and MBH carbonates provides access to highly functionalized ?-aminobutyric acid derivatives in moderate to good yields. Mechanistically, the reaction involves a phosphine-catalyzed tandem SN2′/2-aza-Cope rearrangement/intramolecular addition process.
- Chen, Qingqing,Bao, Yishu,Yang, Xiuqin,Dai, Zonghao,Yang, Fulai,Zhou, Qingfa
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supporting information
p. 5380 - 5383
(2018/09/13)
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- Nucleophilic fluorination facilitated by a CsF-CaF2 packed bed reactor in continuous flow
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A simple to prepare, dry and handle packed bed reactor carrying CsF on CaF2, towards nucleophilic fluorinations in continuous flow, is reported. The reactor also proved adaptable for silyl-ether deprotection and trifluoromethylations with Ruppert's reagent. The study includes reactor stability and scale-up investigations.
- Johansen,Lindhardt
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supporting information
p. 825 - 828
(2018/02/06)
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- On the tandem Morita-Baylis-Hillman/transesterification processes. Mechanistic insights for the role of protic solvents
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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.
- Carpanez, Arthur G.,Coelho, Fernando,Amarante, Giovanni W.
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- Yttrium-catalyzed tandem intermolecular hydroalkoxylation/ claisen rearrangement
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An efficient yttrium-catalyzed tandem intermolecular hydroalkoxylation/Claisen rearrangement has been developed, providing various γ,δ-unsaturated amides in generally good to excellent yields. Importantly, high Z/E selectivity and diastereoselectivity were achieved. Other notable features of this method include widespread availability of the substrates, compatibility with a broad range of functional groups, and mild reaction conditions.
- Zhou, Bo,Li, Long,Liu, Xin,Tan, Tong-De,Liu, Jinxian,Ye, Long-Wu
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p. 10149 - 10157
(2018/05/31)
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- A mixed anhydride approach to the preparation of sulfinate esters and allylic sulfones: Trimethylacetic p-toluenesulfinic anhydride
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A reagent combination of toluenesulfinic acid and trimethylacetyl chloride affords a putative trimethylacetic p-toluenesulfinic anhydride. This reagent has been used to prepare a series of sulfinate esters from primary and secondary alcohols. In addition, the reagent was used to convert Baylis-Hillman substrates into allylic sulfones. Attempts to use the reagent to convert amines to sulfinamides were unsuccessful. In contrast, the use of 2-pyrrolidinone afforded N-p-toluenesulfinyl pyrrolidinone in 64% yield. The use of a chiral 4-benzyl-1,3-oxazolidinone or 4-benzyl-1,3-oxazolidine-2-thione led to the isolation of S-p-tolyl p-toluenethiosulfonate.
- Jacobsen, Eric,Chavda, Mihir K.,Zikpi, Kokou M.,Waggoner, Stephanie L.,Passini, Daniel J.,Wolfe, Jesse A.,Larson, Robert,Beckley, Chelsea,Hamaker, Christopher G.,Hitchcock, Shawn R.
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supporting information
p. 3073 - 3077
(2017/07/17)
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- Efficient synthesis of N-allylated 2-nitroiminoimidazolidine analogues from Baylis–Hillman bromides
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Various Baylis–Hillman–derived new N-allylated 2-nitroiminoimidazolidine analogs were efficiently prepared using potassium carbonate as base. Simple workup procedure, excellent yields, and mild reaction conditions are the salient features of this method. All the synthesized compounds are screened for their larvicidal activity on fourth instar mosquito larvae, Culex quinquefasciatus.
- Kumar, Sriramoju Bharath,Pavan Kumar, Chebolu Naga Sesha Sai,Santhoshi, Amlipur,Kumar, Koochana Pranay,Murthy,Jayathirtha Rao, Vaidya
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supporting information
p. 131 - 136
(2017/01/11)
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- Novel organophosphorus scaffolds of urease inhibitors obtained by substitution of Morita-Baylis-Hillman adducts with phosphorus nucleophiles
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The reactivity of Morita-Baylis-Hillman allyl acetates was employed to introduce phosphorus-containing functionalities to the side chain of the cinnamic acid conjugated system by nucleophilic displacement. The proximity of two acidic groups, the carboxyla
- Ntatsopoulos, Vassilis,Vassiliou, Stamatia,Macegoniuk, Katarzyna,Berlicki, ?ukasz,Mucha, Artur
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supporting information
p. 107 - 120
(2017/04/07)
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- Design, synthesis and evaluation of 3-arylidene azetidin-2-ones as potential antifungal agents against Alternaria solani Sorauer
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A new concise and facile method was explored to synthesize a collection of new 3-arylidene azetidin-2-ones, which could be regarded as the derivatives of the hybrid scaffold of bioactive natural cinnamamide and heterocycle azetidi-2-one. The structures of
- Delong, Wang,Yongling, Wu,Lanying, Wang,Juntao, Feng,Xing, Zhang
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p. 6661 - 6673
(2017/11/17)
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- 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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- Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds
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A rhodium-catalyzed asymmetric synthesis of 5,5-disubstituted cyclohexa-1,3-dienes has been achieved by [2+2+2] cycloaddition reactions between diynes and Morita-Baylis-Hillman (M-B-H) adducts as unsaturated substrates. Products containing two adjacent ch
- Fernández, Martí,Parera, Magda,Parella, Teodor,Lledó, Agustí,Le Bras, Jean,Muzart, Jacques,Pla-Quintana, Anna,Roglans, Anna
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supporting information
p. 1848 - 1853
(2016/06/09)
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- Synthesis of Chiral α-Trifluoromethylamines with 2,2,2-Trifluoroethylamine as a "building Block"
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The β-isocupreidine, a cinchonine derived alkaloid, catalyzed asymmetric SN2′-SN2′ reaction between N-2,2,2-trifluoroethylisatin ketimines and MBH type carbonates was realized in a simple and efficient way. A series of chiral α-trifl
- Li, Xiaoyuan,Su, Jinhuan,Liu, Zhourujun,Zhu, Yuanyuan,Dong, Zhenghao,Qiu, Shuai,Wang, Jiayi,Lin, Li,Shen, Zhiqiang,Yan, Wenjin,Wang, Kairong,Wang, Rui
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supporting information
p. 956 - 959
(2016/03/15)
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- One-pot synthesis of allyl thioacetate from benzaldehydes and activated alkenes using the Morita-Baylis-Hillman reaction as a key step
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An efficient, regioselective and steresoselecitive one-pot protocol for the synthesis of (Z)-S-2-alkoxycarbonyl-3-acylallyl ethanethioates and (E)-S-2-cyano-3-acylallyl ethanethioates from benzaldehydes and activated alkenes (methyl acrylate and acrylonit
- Yang, Hae-Won,Choi, Ji-Su,Lee, Sang-Jin,Yoo, Byung-Woo,Yoon, Cheol Min
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p. 134 - 140
(2016/03/30)
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- An efficient synthesis of dihydrobenzo[c]azepines from Morita-Baylis-Hillman adducts via Pictet-Spengler reaction
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Various dihydrobenzo[c]azepines were synthesized in good yields via Pictet-Spengler cyclization protocol from tosylamide derivatives of Morita-Baylis-Hillman adducts and 1,3,5-trioxane. The synthesis was carried out in the presence of easily removable mon
- Moon, Hye Ran,Kim, Su Yeon,Roh, Hwa Jung,Kim, Jae Nyoung
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supporting information
p. 680 - 684
(2016/05/19)
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- Transition-Metal-Free Cascade Synthesis of 4-Quinolones: Umpolung of Michael Acceptors via Ene Reaction with Arynes
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A novel "one-pot" aryne transformation is described that affords various 4-quinolone derivatives without recourse to transition-metal catalysis. Arynes react with aza-Morita-Baylis-Hillman (AMBH) adducts through a cascade sequence involving an insertion/c
- Santhosh Reddy,Lagishetti, Chandraiah,Kiran, I. N. Chaithanya,You, Hengyao,He, Yun
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supporting information
p. 3818 - 3821
(2016/08/16)
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- Versatile O- and S-functionalized 1,2,3-triazoliums: Ionic liquids for the Baylis-Hillman reaction and ligand precursors for stable MIC-transition metal complexes
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The efficient synthesis of O- and S-functionalized 1,2,3-triazoliums is reported. Owing to their physical properties, these cations are efficient ionic liquids for Baylis-Hillman addition under mild reaction conditions. Simultaneously, the functionalizati
- Mendoza-Espinosa, Daniel,González-Olvera, Rodrigo,Osornio, Cecilia,Negrón-Silva, Guillermo E.,Santillan, Rosa
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supporting information
p. 1587 - 1591
(2015/03/18)
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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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- A versatile approach to noncoded β-hydroxy-α-amino esters and α-amino acids/esters from morita-baylis-hillman adducts
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A simple and straightforward approach to the diastereoselective synthesis of noncoded β-hydroxy-α-amino esters from Morita-Baylis-Hillman (MBH) adducts is described. The strategy is based on a one-pot sequence involving an oxidative cleavage of the double bond of silylated Morita-Baylis-Hillman adducts, followed by the reaction with hydroxylamine hydrochloride/pyridine to form oximes. The stereoselective reduction of the oximes with the mixture MoCl5·nH2O/NaBH3CN led to the corresponding anti-β-hydroxy-α-amino esters in four steps in good overall yield and with diastereoselectivity higher than 95%. A slight modification of the synthetic approach has allowed for the racemic synthesis of a set of noncoded α-amino esters/acids and DOPA
- Ullah, Hamid,Ferreira, Andr V.,Bendassolli, Jos A.,Rodrigues, Manoel T.,Formiga, Andr Luiz B.,Coelho, Fernando
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supporting information
p. 113 - 123
(2015/02/02)
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- Morita-Baylis-Hillman adducts as building blocks of heterocycles: a simple approach to 4-substituted pyrazolones, and mechanism investigation via ESI-MS(/MS)
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Abstract We describe herein an efficient approach for the preparation of 4-substituted 2,3-dihydro-1H-pyrazol-3-ones starting from Morita-Baylis-Hillman adducts. These heterocycles were obtained in two or three steps as single isomers with moderate to goo
- Barcelos, Rosimeire C.,Zeoly, Lucas A.,Rodrigues, Manoel T.,Ferreira, Bruno R. V.,Eberlin, Marcos N.,Coelho, Fernando
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p. 1557 - 1570
(2015/02/19)
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- N-bromosuccinimide-mediated radical cyclization of 3-arylallyl azides: Synthesis of 3-substituted quinolines
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Visible light irradiation of N-bromosuccinimide serves as an effective means to convert methyl 2-(azidomethyl)-3-arylpropenoates and 2-(azidomethyl)-3-arylacrylonitriles to the corresponding iminyl radicals via ?±-hydrogen abstraction and subsequent extrusion of dinitrogen. Thus formed iminyl radicals then undergo intramolecular ortho attack on the aryl ring, affording methyl quin-oline-3-carboxylates and quinoline-3-carbonitriles respectively.
- Wang, Wei-Xia,Zhang, Qing-Zhao,Zhang, Tian-Qi,Li, Zhan-Shan,Zhang, Wei,Yu, Wei
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supporting information
p. 221 - 226
(2015/02/19)
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- Synthesis, characterization and antimicrobial activity of some new Baylis-Hillman derived benzothiazolo pyrimidinone derivatives
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A series of Baylis-Hillman derived 22 new benzothiazolo pyrimidinone derivatives have been synthesized from Baylis-Hillman acetates and 2-amino benzothiazole under neat conditions with high yields. All the newly synthesized compounds have been characteriz
- Gampa, Raghavachary,Chebrolu, Lavanya Devi,Jarapula, Ravi,Vaidya, Jayathirtha Rao,Ghanakota, Venkateshwar Rao,Manda, Sarangapani
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p. 217 - 227
(2015/03/04)
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- Synthesis of thio-heterocyclic analogues from Baylis-Hillman bromides as potent cyclooxygenase-2 inhibitors
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A series of thio-substituted pyrimidine, benzoxazole, benzothiazole and triazole analogues were synthesized from Baylis-Hillman bromides in a clean and efficient way. The synthesized twenty new compounds were subjected to in vitro COX-1 and COX-2 inhibito
- Santhoshi, Amlipur,Mahendar, Budde,Mattapally, Saidulu,Sadhu, Partha Sarathi,Banerjee, Sanjay Kumar,Jayathirtha Rao, Vaidya
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p. 1952 - 1957
(2014/04/17)
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- Catalytic asymmetric one-pot synthesis of α-methylene-γ-lactams
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An organocatalytic enantioselective synthesis of α-methylene-γ- lactams has been developed. The reaction between protected 2-aminomalonates and Morita-Baylis-Hillman carbonates is catalyzed by chiral Lewis bases to afford the corresponding lactams in exce
- Companyó, Xavier,Geant, Pierre-Yves,Mazzanti, Andrea,Moyano, Albert,Rios, Ramon
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- Synthesis of 1-benzhydryl piperazine derivatives and evaluation of their ACE inhibition and antimicrobial activities
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This study presents the synthesis of 14 new 1,4-disubstituted piperazine derivatives from allyl bromides of Baylis-Hillman adduct and 4,4-disubstituted benzhydryl piperazines. All the synthesized compounds were further screened for in vitro ACE inhibitor and antimicrobial activities. Among the synthesized piperazine derivatives, compound 12h showed moderate ACE inhibitor activity as compared to the standard, angiotensin-converting enzyme inhibitor (Sigma). The kinetic data (K m, K i and V max values) of enzyme inhibition for compound 12h and ACE inhibitor standard were also determined. Similarly, all compounds were screened against different bacterial strains. Compounds 12a, 12b, 12d, 12h and 12i showed excellent to moderate activity against various tested bacterial strains. Compounds 12b and 12i showed broad spectrum of antibacterial activity against Pseudomonas aeruginosa, Staphylococcus aureus, S. aureus MLS 16, Escherichia coli, Bacillus subtilis and Klebsiella planticola, while compounds 12a, 12d and 12i showed promising activity against P. aeruginosa (MIC value of 8.96 μM), S. aureus (MIC value of 42.2 μM) and S. aureus MLS 16 (MIC value of 81.3 μM), respectively. The remaining compounds showed activity at a concentration of >491 μM.
- Santhoshi, Amlipur,Kumar, Singam Naveen,Sujitha, Pombala,Poornachandra, Yedla,Sadhu, Partha Sarathi,Kumar, C. Ganesh,Rao, Vaidya Jayathirtha
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p. 3207 - 3219
(2014/05/06)
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- Organocatalytic enantioselective allylic alkylation of MBH carbonates with β-keto esters
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The highly stereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with β-ketoesters catalysed by β-ICD is described. The corresponding products containing two adjacent quaternary and tertiary carbon centers were obtained in good yields with high diastereoselectivity (up to 10 : 1 dr) and enantioselectivity (up to 95% ee).
- Kamlar,Hybelbauerova,Cisarova,Vesely
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supporting information
p. 5071 - 5076
(2014/07/08)
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- Oxidative heck coupling of allylic amines with 2,2,6,6- Tetramethylpiperidine-N-oxyl (TEMPO) as oxidant for the preparation of tetrasubstituted alkenes
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The paper describes the oxidative Heck arylation of various allylic amines using arylboronic acids for the preparation of tetrasubstituted alkenes. As oxidant the commercially available 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) is used and coupling rea
- He, Zhiheng,Wibbeling, Birgit,Studer, Armido
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supporting information
p. 3639 - 3647
(2014/01/06)
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- Regio-and enantioselective bioreduction of methyleneketoesters using both polymeric resin and cellulose matrix
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Methyleneketoesters were prepared in >90% yield by performing an IBX oxidation of Morita-Baylis-Hillman adducts. A methodology was developed to achieve methyl 3-aryl-3-keto-2-methylenepropanoate reduction using a screening of yeast strains in three different reaction procedures to obtain products with both high yield and diastereoselectivity. The reactions conducted in water provided inferior yields (50%) for substrates 2b-c. Employing Amberlite XAD7HP which was a substrate reservoir that also immediately extracted the products from the reaction medium after their formation, syn-4a-c and anti-4a-c were isolated in 60-70% yield, with high stereoselectivity (98-99% ee). The best results were obtained using substrates adsorbed on filter paper which provided products yields above 70%, a 99% ee and a diastereomoeric ratio (syn-4: anti-4) 9:1. Cellulose matrix has excellent potential to be successfully employed in general biocatalytic reactions.
- Chaves, Michel R.B.,Moran, Paulo J.S.,Rodrigues, J. Augusto R.
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- Heterocycles from Morita-Baylis-Hillman adducts: Synthesis of 5-oxopyrazolidines, arylidene-5-oxopyrazolidines, and oxo-2,5-dihydro-pyrazols
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Starting from Morita-Baylis-Hillman (MBH) adducts, an approach for the synthesis of oxopyrazolidines, arylidene-oxopyrazolidines, and oxo-2,5-dihydropyrazoles is described. The method is based on a tandem process involving a Michael addition of amino-guan
- Correia, José Tiago M.,Rodrigues Jr., Manoel T.,Santos, Hugo,Tormena, Cláudio F.,Coelho, Fernando
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p. 826 - 832
(2013/07/25)
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- A facile route for the synthesis 1,4-disubstituted tetrazolone derivatives and evaluation of their antimicrobial activity
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A facile route for the synthesis of 20 new 1,4-disubstituted tetrazolone derivatives from allyl bromides of Baylis-Hillman adducts and various 1-substituted tetrazolones is described. All the synthesized compounds were screened for in vitro antibacterial
- Santhoshi, Amlipur,Sadhu, Partha Sarathi,Sriram, Rekulapally,Sai Pavan Kumar, Chebolu Naga Sesha,Mahendar, Budde,Sarangapani, Manda,Rao, Vaidya Jayathirtha
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p. 3329 - 3340
(2013/07/19)
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- New antifungal scaffold derived from a natural pharmacophore: Synthesis of α-methylene-γ-butyrolactone derivatives and their antifungal activity against Colletotrichum lagenarium
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Thirty new and thirty-four known analogues were designed and synthesized to improve the potential use of the α-methylene-γ-butyrolactone ring, a natural pharmacophore. All structures were confirmed by 1H and 13C NMR, MS, and single-c
- Jun-Tao, Feng,De-Long, Wang,Yong-Ling, Wu,He, Yan,Xing, Zhang
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supporting information
p. 4393 - 4397
(2013/07/26)
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- Synthesis of 1,3-thiazine-2,4-diones with potential anticancer activity
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2-Amino-1,3-thiazin-4-ones were subjected to acetylation followed by mild acid hydrolysis to give compounds containing the 1,3-thiazine-2,4-dione core. The potential of these S,N-containing heterocycles as antitumor agents against human cancer cell lines,
- Ferreira, Misael,Assun??o, Laura Sartori,Filippin-Monteiro, Fabíola Branco,Creczynski-Pasa, Tania Beatriz,Sá, Marcus Mandolesi
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p. 411 - 418
(2013/11/19)
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- An efficient and recyclable DMAP-based ionic liquid/water system for Morita-Baylis-Hillman reactions
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The efficient and recyclable system, DMAP-based ionic liquid/water, has been developed and used in the Morita-Baylis-Hillman reaction of aromatic aldehydes with acrylates. The coupling reactions under the described basic reaction conditions proceed quickl
- Zhang, Li-Rong,Yi, Feng-Ping,Zhang, Xuan,Zou, Jian-Zhong
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experimental part
p. 418 - 420
(2012/09/22)
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