3623-15-2Relevant academic research and scientific papers
Synthesis and binding affinities for 5-HT(1A), 5-HT(2A) and 5-HT(2C) receptors of a series of 1- and 2-(4-arylpiperazinylalkyl)-4-(benzoyl)-1,2,3- triazole derivatives
Caliendo, Giuseppe,Fiorino, Ferdinando,Grieco, Paolo,Perissutti, Elisa,Santagada, Vincenzo,Albrizio, Stefania,Spadola, Loredana,Bruni, Giancarlo,Romeo, Maria Rosaria
, p. 719 - 727 (1999)
A number of 1- and 2-(4-arylpiperazinylalkyl)-4-(benzoyl)-1,2,3-triazole derivatives (1-4) were prepared in order to obtain compounds with a high affinity and selectivity for 5-HT(1A) receptors. 5-HT(1A), 5-HT(2A) and 5- HT(2C) affinities were determined by radioligand binding experiments and the most active compounds were also tested for binding affinities on dopaminergic D-1, D-2 and adrenergic α1, α2 receptors. The modification of aromatic substituents, the length of the alkyl chain and its position on the 4- benzoyl-1,2,3-triazole ring were explored. Most of the considered compounds generally showed moderate to high affinity for the 5-HT(1A) receptor binding site. Three derivatives 2c, 3c and 3e bind to 5-HT(1A) receptors in the nanomolar range (IC50 values = 2, 7.2 and 2.6 nM respectively). The most active compound, 2c, presented a high degree of selectivity versus all considered receptors. It was found that the benzoyltriazole derivatives 1h and 4c are new selective ligands for 5-HT(2A) (IC50 = 89 nM) and 5-HT(2C) receptors (IC50 = 17 nM), respectively.
Fine-tuning dirhodium compounds with bridging ligands: Synthesis, structure, catalytic efficiency
Ning, Yangbo,Tan, Jiantao,Wang, Yuanhua,Wang, Zhifan
supporting information, (2021/09/28)
The structure of dirhodium compounds contains a unique Rh-Rh bond, two axial ligands and four bridging ligands. In the dirhodium(II) compounds, it is easy to migrate the coordinating atoms of the bridging ligand during the catalysis process, which leads to the degradation of the catalyst. Coordination atom migration was identified in bridging ligands. To improve the catalyst stability, we carried out a study on the effect of fine-tuning of the bridging ligand on the dirhodium compound. Several dirhodium compounds were designed and synthesized. During this process, we have successfully found Rh2(5-Br-esp)2 and Rh2(5-tBu-esp)2, which are closer to the ideal geometric configuration of the dirhodium(II) compounds. Rh2(5-Br-esp)2 has been applied in the oxidation of propargyl position and Rh2(5-tBu-esp)2 in the formation reaction of the C–N bond.
SBA-15 Supported 1-Methyl-2-azaadamanane N-Oxyl (1-Me-AZADO) as Recyclable Catalyst for Oxidation of Alcohol
Tian, Yangwu,Guo, Xiaqun,Li, Meichao,Li, Chunmei,Hu, Xinquan,Jin, Liqun,Sun, Nan,Hu, Baoxiang,Shen, Zhenlu
supporting information, p. 3928 - 3932 (2021/05/26)
Herein, we designed and synthesized an SBA-15 supported 1-methyl-2-azaadamanane N-oxyl (1-Me-AZADO) and investigated its catalytic performance for selective oxidation of alcohols under Anelli's conditions. The first example of immobilization of 1-Me-AZADO was very important to advance the oxgenation effectively because this supported N-oxyl has excellent catalytic activity for oxidation of alcohols to carbonyl compounds, and more importantly, it can be conveniently recovered and reused at least 6 times without significant effect on its catalytic efficiency.
Solvent-controlled two-step one-pot syntheses of α-X (X = Br or Cl) enamino ketones/esters and 3-(2,5-dioxopyrrolidin-1-yl)acrylate by using terminal carbonyl alkynes
Chen, Guang,Chen, Kaiwei,Chen, Xiao Yun,Chen, Yan,Cheng, Xiaofang,Sun, Chenyang,Tang, Yaonan,Yuan, Shuxia,Zheng, Shaojun,Zhu, Baocheng
supporting information, p. 7914 - 7919 (2021/09/28)
A new two-step one-pot aminobromination/chlorination of carbonyl alkynes has been achievedviaa Michael addition of aliphatic secondary amines and subsequent β-bromination/chlorination of the obtained enamines to afford various α-X (X = Br or Cl) enamino ketones/esters in moderate to good yields. A solvent-controllable protocol has been developed to produce versatile 3-(2,5-dioxopyrrolidin-1-yl)acrylates in moderate yields by using toluene as the solvent and chain alkyl propiolates as alkynyl substrates.
Multisubstituted pyrazole synthesis via [3?+?2] cycloaddition/rearrangement/N[sbnd]H insertion cascade reaction of α-diazoesters and ynones
Feng, Xiaoming,Liu, Xiaohua,Zeng, Zi,Zhao, Peng
supporting information, p. 132 - 135 (2020/12/21)
The cascade reactions of alkyl α-diazoesters and ynones using Al(OTf)3 as the catalyst are described. A series of 4-substituted pyrazoles were obtained via [3 + 2] cycloaddition, 1,5-ester shift, 1,3-H shift, and N[sbnd]H insertion process. Deuterium labelling experiments, kinetic studies and control experiments were carried out for the rationalization of the mechanism.
Microwave-assisted multicomponent synthesis of benzo[f]pyrrolo[1,2-a]quinoline derivatives
Georgescu, Emilian,Georgescu, Florentina,Dumitrascu, Florea,Draghici, Constantin,Nicolescu, Alina,Marinescu, Daniela,Deleanu, Calin
, p. 97 - 102 (2021/02/05)
We present an efficient one-pot, three component microwave-assisted synthesis of benzo[f]pyrrolo[1,2-a]quinoline derivatives starting from benzo[f]quinoline, 2-bromo-acetophenones or 2-chloro-(N-phenyl)acetamides and electron-deficient alkynes. This synthetic strategy provides a direct and easy access to a range of novel benzo[f]pyrrolo[1,2-a]quinoline derivatives. The method has the advantages of considerable shorter reaction time, reduced solvent consumption, operational simplicity and minimal impact on the environment. Nine new benzo[f]pyrrolo[1,2-a]quinoline derivatives have been synthesized with the new method and they are fully characterized.
Mono-Gold(I)-Catalyzed Enantioselective Intermolecular Reaction of Ynones with Styrenes: Tandem Diels–Alder and Ene Sequence
Nanko, Masaki,Inaba, Yuya,Sekine, Keisuke,Mikami, Koichi
, (2021/02/05)
Gold-catalyzed intermolecular reaction leading to dihydronaphthalene derivatives in one pot from two equivalents of ynones with respect to styrene is uncovered. The [4+2] Diels–Alder cycloaddition of ynones and styrenes is catalyzed by a mono-gold(I) complex and the conjugated acid to provide an unstable 3,8a-dihydronaphthalene to subsequently undergo an intermolecular ene-type reaction with the π-activated ynone to afford multi-component coupling dihydronaphthalene products. Linear relationships between chiral ligand-gold complexes and chiral dihydronaphthalene products proves mono-gold catalysis that triggers an asymmetric tandem Diels–Alder and ene reaction sequence.
Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis
Chen, Violet Yijang,Kwon, Ohyun
supporting information, p. 8874 - 8881 (2021/03/17)
Polyalkyl furans are widespread in nature, often performing important biological roles. Despite a plethora of methods for the synthesis of tetrasubstituted furans, the construction of tetraalkyl furans remains non-trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael–Heck approach, using sequential phosphine-palladium catalysis, for the preparation of various polyalkyl furans from readily available precursors. The versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes, namely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran; the marine natural products plakorsins A, B, and D and plakorsin D methyl ester; and the furan fatty acids 3D5 and hydromumiamicin.
Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures
Delost, Michael D.,Njardarson, Jon T.
supporting information, p. 6121 - 6125 (2021/08/16)
We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.
Laccase-mediated Oxidations of Propargylic Alcohols. Application in the Deracemization of 1-arylprop-2-yn-1-ols in Combination with Alcohol Dehydrogenases
González-Granda, Sergio,Méndez-Sánchez, Daniel,Lavandera, Iván,Gotor-Fernández, Vicente
, p. 520 - 527 (2019/11/16)
The catalytic system composed by the laccase from Trametes versicolor and the oxy-radical TEMPO has been successfully applied in the sustainable oxidation of fourteen propargylic alcohols. The corresponding propargylic ketones were obtained in most cases in quantitative conversions (87–>99 % yield), demonstrating the efficiency of the chemoenzymatic methodology in comparison with traditional chemical oxidants, which usually lead to problems associated with the formation of by-products. Also, the stereoselective reduction of propargylic ketones was studied using alcohol dehydrogenases such as the one from Ralstonia species overexpressed in E. coli or the commercially available evo-1.1.200, allowing the access to both alcohol enantiomers mostly with complete conversions and variable selectivities depending on the aromatic pattern substitution (97–>99 % ee). To demonstrate the compatibility of the laccase-mediated oxidation and the alcohol dehydrogenase-catalyzed bioreduction, a deracemization strategy starting from the racemic compounds was developed through a sequential one-pot two-step process, obtaining a selection of (S)- or (R)-1-arylprop-2-yn-1-ols with excellent yields (>98 %) and selectivities (>98 % ee) depending on the alcohol dehydrogenase employed.
