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Biginelli反应
POLYMER · 2015 · IF 3.562

One-pot polymer conjugation on carbon nanotubes through simultaneous π–π stacking and the Biginelli reaction

Xu Ren,Bin Yang,Yuan Zhao,Xiaoyong Zhang,Xing Wang,Yen Wei,Lei Tao

The Biginelli reaction has been utilized as an effective click reaction to collaborate with π–π stacking to prepare carbon nanotube-polymer conjugates. The synthesized polymers are successfully anchored on carbon nanotube surface via ‘grafting to’ strategy, and the obtained carbon nanotube-polymer composites possessing characteristic properties of anchored polymer can be well dispersed in general solution to expand carbon nanotubes application realm.

研究领域: 材料科学 · 化学工程
✓ 已验证 DOI 高影响因子
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CATALYSIS LETTERS · 2013 ·Vol. 143 ·期 5 ·463-468 · IF 2.244

One-Pot Synthesis of 3,4-Dihydro-2(H)-Pyrimidinones Catalyzed by Reusable Acidic Choline-Based Ionic Liquids

Zhu Anlian,Li Qianqian,Li Lingjun,Wang Jianji

Abstract A series of choline-based ionic liquids (CIL) have been synthesized in this work. The results suggested that both the cations and the anions have significant influences on their properties such as thermostabilities, acidities and their performances for the synthesis of 3,4-dihydro-2(H)-pyrimidinones. The optimized catalytic system based on the CIL [DMEA][HSO 4 ] for the Biginelli reactions benefits from the wide substrates tolerance, benign reaction conditions, easy work-up procedures, and the feasible reusability of the ionic liquid. Graphical Abstract The thermostabilities, acidities, and the catalytic activities for the Biginelli reactions are all follows the sequence of [DMEA][HSO 4 ] > [Choline] [HSO 4 ] > [DMEA][H 2 PO 4 ] > [Choline] [H 2 PO 4 ] .

研究领域: 有机化学 · 催化化学 · 药物合成
✓ 已验证 DOI 高影响因子
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RSC Advances · 2024 ·Vol. 14 ·期 25 ·17440-17447 · IF 3.9

Biodegradable polyester copolymers: synthesis based on the Biginelli reaction, characterization, and evaluation of their application properties

Kai Lu,Xinyi Shen,Yunhai Shi,Zejian He,Dahong Zhang,Mi Zhou

The Biginelli reaction, a three-component cyclocondensation reaction, is an important member of the multicomponent reaction (MCR) family. In this study, we conducted end-group modifications on a variety of biodegradable polyesters, including poly(1,4-butylene adipate) (PBA), poly(ε-caprolactone) (PCL), polylactic acid (PLA), and poly(p-dioxanone) (PPDO), based on the precursor polyethylene glycol (PEG). By combining two polymers through the Biginelli multi-component reaction, four new biodegradable polyester copolymers, namely DHPM–PBA, DHPM–PCL, DHPM–PLA, and DHPM–PPDO, were formed. These Biginelli reactions demonstrated exceptional completeness, validating the efficiency of the synthesis strategy. Although the introduction of various polyesters lead to different properties, such as crystallinity and cytotoxicity, the newly synthesized 3,4-dihydro-2(H)-pyrimidinone compounds (DHPMs) exhibit enhanced hydrophilicity and can self-assemble in water and N,N-dimethylformamide (DMF) solution to form micelles with a controllable size. Furthermore, DHPM–PPDO promotes cellular growth and has potential applications in wound healing and tissue engineering. In conclusion, this method demonstrates great universality and methodological significance and offers insights into the medical applications of polyethylene glycol.

研究领域: 材料科学 · 生物学 · 医学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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MICROPOROUS AND MESOPOROUS MATERIALS · 2021 · IF 5.455

Seed-assisted direct synthesis of aluminosilicate form of ITQ-58 zeolite

Qintong Huang,Ningyue Chen,Mengyun Wen,Weichi Liang,Rui Li,Yukai Zhao,Zhifeng Zeng,Chuanqi Zhang,Jiuxing Jiang

The aluminosilicate form of ITQ-58 has been directly synthesized in the synthesis gel SiO 2 -Al 2 O 3 -Na 2 O-H 2 O using Si/B-ITQ-58 zeolite as seed. Si/Al-ITQ-58 exhibits good crystallinity, high surface area, tetrahedral Al 3+ species, and middle acid sites. The acidic form of Si/Al-ITQ-58 zeolite, is an excellent alternative heterogeneous catalyst with high yield and simple product separation, used for Biginelli reaction. Therefore, with the second case, we further confirm the new function of seed-assisted synthesis, i.e., direct aluminosilicate preparation.

研究领域: 材料科学 · 化学工程 · 催化
✓ 已验证 DOI 高影响因子
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JOURNAL OF BIOTECHNOLOGY · 2013 · IF 3.183

Trypsin-catalyzed tandem reaction: One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones by in situ formed acetaldehyde

Zong-Bo Xie,Na Wang,Wan-Xia Wu,Zhang-Gao Le,Xiao-Qi Yu

A simple, mild, one-pot tandem method catalyzed by trypsin was developed for the synthesis of 3,4-dihydropyrimidin-2(1 H )-ones by the Biginelli reaction of urea, β-dicarbonyl compounds, and in situ-formed acetaldehyde. Trypsin was found to display dual promiscuous functions to catalyze transesterification and the Biginelli reaction in sequence.

研究领域: 生物化学 · 有机合成
✓ 已验证 DOI PubMed 高影响因子
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CATALYSIS COMMUNICATIONS · 2016 · IF 3.389

Halogenated macroporous sulfonic resins as efficient catalysts for the Biginelli reaction

Pengfei Shen,Mancai Xu,Dulin Yin,Shaoan Xie,Chan Zhou,Fada Li

A series of halogenated macroporous sulfonic resins A-15-Cl, A-15-Br and A-15-I were synthesized from the precursor Amberlyst 15 by a typical halogenation reaction, and they were evaluated for the catalytic activities of the halogenated macroporous sulfonic resins via the Biginelli reaction in detail. These modified resins possessed a larger contact angle of water droplet than the precursor and a significantly improved thermal stability, which contributed to their higher catalytic activity. In particular, the resin A-15-Br containing 31.27% bromine exhibited the best catalytic activity and excellent recyclability.

研究领域: 有机化学 · 催化材料科学
✓ 已验证 DOI 高影响因子
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JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY · 2017 · IF 4.421

An efficient, recyclable and large-scalable fiber-supported Fe(III) catalytic system on a simple fixed-bed reactor verified in the Biginelli reactions

Xian-Lei Shi,Yongju Chen,Qianqian Hu,Feng Wang,Peigao Duan

An efficient, recyclable and large-scalable fiber-supported Fe(III) catalytic system verifed in the one-pot multicomponent Biginelli reactions, is presented. The fiber catalyst was prepared conveniently from commercially available polyacrylonitrile fiber according to a simple two-step procedure by amination and chelation in water, and characterized detailedly with ICP analysis, morphology, mechanical properties, elemental analysis, FTIR spectroscopy, and SEM during the modification and utilization processes. Moreover, the fiber catalyst-mediated reactions showed broad applicability and proceeded smoothly to afford a series of substituted 3,4-dihydropyrimidin-2-(1 H )-ones/-thiones (yields 81–94%) in ethanol under mild conditions. Furthermore, the newly developed fiber catalyst held high strength, good flexibility and exhibited excellent stability and recyclability (over 10 cycles), and the procedure was operationally concise and effectively amenable to the gram-scale on a simple fixed-bed reactor with potential industrialization prospect.

研究领域: 有机化学 · 催化材料科学
✓ 已验证 DOI 高影响因子
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JOURNAL OF COLLOID AND INTERFACE SCIENCE · 2018 · IF 5.091

Synthesis and biological imaging of cross-linked fluorescent polymeric nanoparticles with aggregation-induced emission characteristics based on the combination of RAFT polymerization and the Biginelli reaction

Jiande Dong,Meiying Liu,Ruming Jiang,Hongye Huang,Qing Wan,Yuanqing Wen,Jianwen Tian,Yanfeng Dai,Xiaoyong Zhang,Yen Wei

Fluorescent probes have long been regarded as tools for imaging living organisms with advantages such as high sensitivity, good designability and multifunctional potential. Many fluorescent probes, especially the probes based on aggregation-induced emission (AIE) dyes, have received increasing attention since the AIE phenomenon was discovered. These AIE dye-based fluorescent probes could elegantly overcome the notorious quenching effect caused by aggregation of conventional organic dyes. However, it is still difficult to directly apply these AIE-active dyes for biomedical applications owing to their hydrophobic nature. Therefore, the development of novel and facile strategies to endow them with water dispersibility is of critical importance. In this work, we exploit an efficient and simple strategy to fabricate an AIE dye-based fluorescent copolymer through the combination of reversible addition-fragmentation chain transfer and the Biginelli reaction . Moreover, the copolymer can self-assemble to fluorescent polymeric nanoparticles (FPNs) in water solution. Hydrophilic poly(PEGMA- co -AEMA) was reacted with the AIE-active dye 4′,4‴-(1,2-diphenylethene-1,2-diyl)bis([1,1′-biphenyl]-4-carbaldehyde (CHO-TPE-CHO) to form amphiphilic luminescent polymers using urea as the connection bridge. The successful synthesis of the final products (poly(PEGMA- co -AEMA-TPE) FPNs) was confirmed by various instruments. Furthermore, Transmission electron microscopy (TEM) images manifest that poly(PEGMA- co -AEMA-TPE) copolymers will self-assemble into spherical nanoparticles in aqueous environments with sizes between 100 nm and 200 nm. The cell uptake and bioimaging experiment confirm that poly(PEGMA- co -AEMA-TPE) FPNs have excellent biocompatibility and emit strong green fluorescence in a cellular environment. Thus, poly(PEGMA- co -AEMA-TPE) FPNs are excellent candidates for biomedical applications.

研究领域: 材料科学 · 生物医学工程 · 化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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BIOORGANIC CHEMISTRY · 2020 · IF 4.831

Efficient biocatalytic strategy for one-pot Biginelli reaction via enhanced specific effects of microwave in a circulating reactor

Zong-Bo Xie,Lei-Han Fu,Jia Meng,Jin Lan,Zhi-Yu Hu,Zhang-Gao Le

A one-pot efficient biocatalytic strategy for the synthesis of 3,4-dihydropyrimidin-2-(1 H )-ones was developed in a circulating microwave reactor selecting α-chymotrypsin as the promiscuous biocatalyst. In the circulating reaction system, the combination of microwave heating and external cooling could avoid the denaturation and inactivation of enzyme, and greatly improved the radiation power of microwave, thus improving the specific effects of microwave. During the reaction process, the microwave radiation power was automatically adjusted by adjusting the speed of the reaction mixture circulation. When the microwave power was maintained at 110 W, the best results could be obtained with the highest yield of 96% at 55 °C in 50 min, and the reaction had a wide range of substrates. But no obvious product was detected in a tank microwave reactor at 55 °C for 100 min, under this condition, the microwave power was maintained at about 3 W. As a contrast, the reaction only obtained 63% yield in 55 °C oil bath for 96 h.

CAS / MDL: 9048-46-8 9004-07-3
研究领域: 有机化学 · 生物催化 · 合成化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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World Journal of Engineering · 2020 ·Vol. 17 ·期 1 ·21-26 · IF 0

Long-chain Brønsted acidic ionic liquids catalyzed one-pot three-component Biginelli reaction

Leqin He,Shenjun Qin,Jianjun Liu,Wei Zhao,Tao Chang

PurposeFrom the atom economy and environmentally friendly point of views, the development of clean and green approaches using ionic liquids (ILs) as recyclable catalysts has attracted increasing attention. The purpose of this study is to investigate the effect of task-specific ILs content on the one-pot three-component Biginelli reaction.Design/methodology/approachA series of halogen-free quaternary ammonium ILs functionalized with –SO3H group were prepared and characterized by1H nuclear magnetic resonance (NMR),13C NMR and electrospray ionization mass spectrometry. The ILs were used as catalysts for Biginelli reaction among aromatic aldehydes, urea or thiourea and β-dicarbonyl compounds. Anions and cations of ILs were varied to observe their effects on and contributions to the catalysts. The influencing factors, such as the amount of catalyst, solvent, reaction time and reaction temperature, were investigated.FindingsThe effect and contribution of cations of ILs were observed. Results showed that 3-(N, N-dimethylhexadecylammonium) propanesulfonic acid toluene sulfate ([DHPA][Tos]) showed comparable catalytic activity. Good adaptability to the reaction substrate and maximum product yield was observed when [DHPA][Tos] was used as catalyst. It was found that Biginelli reaction catalyzed by 10 mol% [DHPA][Tos] for 3 h under solvent-free conditions at 80 °C gave the best yield of 94%. Post-processing steps were simple, and the catalyst could be reused easily.Originality/valueThis paper demonstrates that ILs containing a long carbon chain and a bulky Tos anion efficiently promoted the reaction, in which the long carbon chains facilitate mass transfer in the reaction system.

研究领域: 有机化学 · 催化化学
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JOURNAL OF BIOTECHNOLOGY · 2020 · IF 3.503

Enzyme-catalysed one-pot synthesis of 4H-pyrimido[2,1-b] benzothiazoles and their application in subcellular imaging

Yuan Yu,Wei Zhang,Qing-Tian Gong,Yan-Hong Liu,Zeng-Jie Yang,Wei-Xun He,Na Wang,Xiao-Qi Yu

Enzymes, which provide more efficient and eco-friendly strategies for various functional molecules’ construction than traditional chemo-catalysts, were utilized for the synthesis of 4H -pyrimido[2,1- b ] benzothiazole derivatives. Reported herein is a trypsin-catalysed three- component Biginelli reaction of aldehyde, β-ketoester and 2-amino benzothiazole in one pot, affording a streamlined pathway to diverse ring-fused pyrimidines. In addition to using commercially available aromatic aldehydes as substrates, acetaldehyde, the chemical liquid with rather low boiling point and difficult to handle above room temperature, is utilized to further extend the range of substrates. It was verified that most of the tested substrates exhibited satisfactory reactivity. In addition, several substrates indicated AIE (Aggregation-Induced Emission) property and have been investigated as potential biomarkers.

研究领域: 有机化学 · 生物医学 · 材料科学
✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF MATERIALS RESEARCH · 2019 ·Vol. 34 ·期 17 ·3011-3019 · IF 1.982

Amphiphilic fluorescent copolymers via one-pot synthesis of RAFT polymerization and multicomponent Biginelli reaction and their cells imaging applications

Zengfang Huang,Runze Wang,Yali Chen,Xiaobo Liu,Liucheng Mao,Jinying Yuan,Lei Tao,Yen Wei,Xiaoyong Zhang

In this contribution, we devoted ourselves to fabricating aggregation-induced emission (AIE) activity copolymers via one-pot combination of RAFT polymerization and Biginelli reaction for the first time. When the feeding ratio of TPB was 33.5%, the molar fraction of TPB was, respectively, about 14.2 and 22.5% in PEG-PTE1 copolymers by two-step strategy and PEG-PTE2 copolymers by one-pot strategy with the similar structure. The Mn of PEG-PTE1 increased to 59,300 from 52,800 of PEG-AE presoma with narrow PDI, which was more than Mn of PEG-PTE2 with 52,300. As compared with PEG-PTE2, when the feeding ratio of TPB was 48.6%, the molar fraction of TPB increased to 32.6% in PEG-PTE3. In aqueous solution, the as-obtained PEG-PTE2 copolymers can self-assemble into fluorescent organic nanoparticles (FONs) with 100–180 nm spherical morphology, the maximal emission peak of which presented at 460 nm with the obvious AIE phenomenon. Moreover, due to the low toxicity and excellent cell dyeing behavior, the as-prepared PEG-PTE2 copolymers displayed great potential for biomedical applications.

研究领域: 高分子化学 · 生物材料 · 分子影像学 · 纳米医学 · 化学生物学
✓ 已验证 DOI 高影响因子
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