28867-76-7Relevant articles and documents
Small molecular chromogenic sensors for Hg2+: A strong "push-pull" system exists after binding
Fu, Yanyan,Li, Hongxiang,Hu, Wenping
, p. 2459 - 2463 (2007)
Two small molecular chromogenic sensors 1 and 2 for detection of Hg 2+ are described. After coordination with Hg2+, a red shift of about 100 nm was observed in the UV/Vis spectra and the color of the solution changed from pale yellow to red which could easily be detected by the naked eye. The results indicate a strong push-pull system was formed after coordination of Hg2+. The 1H NMR spectra and control experiments showed the binding sites of 1 and 2 to be the aniline groups rather than the azine bridge. Moreover, mercury test papers were made by adsorbing 1 onto filter paper, allowing heterogeneous sensing of Hg2+ in aqueous solution. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
General and Greener Synthesis of Diverse Functional Organic Salts through Schiff Base Chemistry
Hu, Baoping,Shi, Qingrong,Lu, Feipeng,Zhang, Pengcheng,Peng, Panpan,Zhao, Chaofeng,Du, Yao,Su, Hui,Li, Shenghua,Pang, Siping,Nie, Fudie
, p. 910 - 918 (2019)
We report a greener and more-general organic method for the synthesis of functional organic salts containing organic anions through a Schiff base reaction between readily available aldehydes and simple aminoguanidinium salts. This reaction is operationally simple, free of metal salts, and forms water as the sole byproduct. The broad scope and good functional-group compatibility of this method permit its use to provide ready access to a library of more than 70 distinct organic salts, including those of heterocyclic anions, complex pharmaceutical anions, and polyanions, which are difficult to obtain through classical inorganic methods. Moreover, choosing different aldehydes and organic anions provides a convenient method for modulating or improving the functional properties of the designed organic salts, such as their melting points, fluorescence, and energetic properties. We therefore expect that this method will open new opportunities for the discovery and functionalization of a wide variety of organic salts and functional materials.
Spectroscopic and theoretical studies on symmetric aryl azines
Karthikeyan, Balakrishnan,Jayabharathi, Jayaraman,Thanikachalam, Venugopal
, p. 636 - 638 (2007)
Azines, which closely resemble azobenzenes, have important applications in the field of nonlinear optics. NMR and IR spectroscopic study of some symmetric aryl azines has been undertaken with the aid of ab initio theoretical calculations. All data indicated that the structure of azine and substituted azines is the symmetric trans form.
Design, synthesis and biological evaluation of Schiff’s base derivatives as multifunctional agents for the treatment of Alzheimer’s disease
Shi, Jian,Zhou, Yi,Wang, Keren,Ma, Qinge,Wei, Rongrui,Li, Qingfeng,Zhao, Yiyang,Qiao, Zhanpin,Liu, Shuang,Leng, Yumin,Liu, Wenmin,Sang, Zhipei
, p. 624 - 634 (2020/11/30)
A series of Schiff’s base derivatives was rationally designed, synthesized, and evaluated as multi-function agents for the treatment of Alzheimer’s disease (AD). The results revealed that compound 3b was a novel multifunctional agent. It acted as a highly selective monoamine oxidase-B inhibitor (IC50 = 8.4 nM), which was explained by the docking study. Compound 3b also was an antioxidant agent (2.3 eq) and could significantly inhibit self-induced Aβ1-42 aggregation (31.8%). Meanwhile, compound 3b was a selective metal chelator and could inhibit Cu2+-induced Aβ1-42 aggregation (62.3%). Furthermore, compound 3b presented good neuroprotective effects on H2O2-induced PC12 cell injury. More importantly, compound demonstrated good blood brain barrier permeability and druglike properties. Therefore, compound 3b, a promising multi-targeted active molecule, offers an attractive starting point for further study in the drug-discovery process against AD.[Figure not available: see fulltext.].
Synthesis of 1,3-dialkyl-4-[(arylmethylidene)amino]glycolurils
Es’kova, Marina А.,Gazieva, Galina А.,Kolotyrkina, Natalya G.,Kostikova, Natalya N.,Serkov, Sergei А.,Sigay, Natalya V.,Volkhina, Tatyana N.
, p. 646 - 655 (2021/07/06)
[Figure not available: see fulltext.] A method for the synthesis of 1,3-dialkyl-4-[(arylmethylidene)amino]glycolurils was developed based on nucleophilic substitution of the sulfur atom with the oxygen atom in the corresponding thioglycolurils via alkylation of the latter followed by acid hydrolysis of alkylsulfanyl derivatives of thioglycolurils, both with the isolation of alkylsulfanyl intermediates and by the one-pot method. The structure of the synthesized compounds was confirmed by X-ray structural analysis of several examples.
Dihydrazone-based dynamic covalent epoxy networks with high creep resistance, controlled degradability, and intrinsic antibacterial properties from bioresources
Feng, Jie,Li, Qiong,Liu, Yanlin,Lu, Na,Ma, Songqi,Wang, Sheng,Wu, Jiahui,Xu, Xiwei,Yang, Jintao,Zhu, Jin
, p. 11261 - 11274 (2020/06/17)
Covalent adaptable networks (CANs) provide a promising approach to solve the issue of recycling thermosets due to their dynamic cross-linked networks. However, CANs are susceptible to creep at relatively low temperatures, and their chemical stability is also inevitably doubtful. Here, we designed novel dihydrazone CANs by cross-linking a dihydrazone-containing epoxy monomer, which was synthesized from the condensation of a lignin derivative vanillin and hydrazinium hydrate, followed by a reaction with epichlorohydrin. Besides the excellent malleability and reprocessability, the dihydrazone CANs exhibited a high initial creep temperature of ～105 °C, which was ascribed to the superior stability of the hydrazone bond at around 100 °C and favorable hydrazone exchangeability at elevated temperatures. Meanwhile, the degradation of the dihydrazone CANs exhibited temperature, solvent, and acidity dependence. Moreover, on account of the high antibacterial properties of the hydrazone bond, the CANs presented a high killing rate (95.8%) for Gram-negative bacteria (E. coli). Thus, this work discloses an effective dynamic covalent motif for the development of CANs with excellent dimensional stability, chemical resistance, and intrinsic antibacterial properties.
Cp*Co(III)-catalyzed C[sbnd]H amidation of azines with dioxazolones
Huang, Yanzhen,Pi, Chao,Tang, Zhen,Wu, Yangjie,Cui, Xiuling
supporting information, p. 3237 - 3240 (2020/09/15)
Cp*Co(III)-catalyzed direct C[sbnd]H amidation of azines has been developed. This conversion could proceed smoothly in the absence of external oxidants, acids or bases, with excellent regioselectivity and broad functional group tolerance. CO2 w
Ligand Redox-Controlled Tandem Synthesis of Azines from Aromatic Alcohols and Hydrazine in Air: One-Pot Synthesis of Phthalazine
Chakraborty, Mou,Sengupta, Debabrata,Saha, Tanushri,Goswami, Sreebrata
supporting information, p. 7771 - 7778 (2018/06/11)
A controlled tandem synthetic route to azines from various alcohols and hydrazine hydrate by the use of a Ni(II) complex of 2,6-bis(phenylazo)pyridine as a catalyst is reported. In marked contrast to the previous report, the reaction is operative using an earth-abundant metal catalyst, milder reaction conditions, and aerobic conditions, which though are desirable but unprecedented in the literature. The catalytic reaction has a vast substrate scope including a single-step synthesis of phthalazine from 1,2-benzenedimethanol and hydrazine hydrate via intramolecular coupling. Mechanistic investigation suggests that the coordinated ligand redox controls the reaction by the use of a reversible azo (N=N)/ hydrazo (NH - NH) redox couple where the metal center is used primarily as a template.
Selective Reduction of Azines to Benzyl Hydrazones with Sodium Borohydride Catalyzed by Mesoporous Silica-Supported Silver Nanoparticles: A Catalytic Route towards Pyrazole Synthesis
Charistoudi, Evangelia,Kallitsakis, Michael G.,Charisteidis, Ioannis,Triantafyllidis, Kostas S.,Lykakis, Ioannis N.
supporting information, p. 2949 - 2960 (2017/09/08)
The catalytic activity of supported silver nanoparticles on mesoporous silica was studied, for the selective reduction of azines into benzyl hydrazones using sodium borohydride as mild reducing agent. Different sizes of silver nanoparticles supported on mesoporous silica (Ag/HMS) were successfully prepared by two methods, i.e., wet impregnation followed by reduction with hydrogen at 350 °C and in situ deposition/reduction with a mixture of amines (ethanolamine and ethylenediamine). The Ag/HMS (amines) catalyst was found to promote the selective 1,2-reduction of aryl-substituted azines, compared to the corresponding 1,4-reduction that occurs in general reduction processes. This catalytic transfer hydrogenation process found to be clean, fast and quantitative (>99% yields and selectivity) towards benzyl hydrazone synthesis under mild conditions. Of great importance is that under the present catalytic conditions reducible functional groups remain intact. Formal kinetics, support the in situ formation of silver hydride species being responsible for the reduction process. The presence of protic polar methanol enhanced the catalytic activity of Ag/HMS. Based on the recycling studies the catalytic system Ag/HMS-NaBH4 was found to catalyze the selective reduction of azines nine times without significant loss of its activity. Finally, a one-pot reaction between the in situ produced benzyl hydrazones and a series of nitrostyrenes readily provided the regioselective synthesis of 1,3,5-subtituted pyrazoles, highlighting a useful synthetic application of the catalytic protocol. (Figure presented.).
Simple and efficient approach for synthesis of hydrazones from carbonyl compounds and hydrazides catalyzed by meglumine
Zhang, Mo,Shang, Ze-Ren,Li, Xiao-Tang,Zhang, Jia-Nan,Wang, Yong,Li, Kang,Li, Yang-Yang,Zhang, Zhan-Hui
, p. 178 - 187 (2017/01/10)
A simple, environmentally benign protocol for synthesis of hydrazones from carbonyl compounds and hydrazides has been developed in the presence of meglumine in aqueous-ethanol media at room temperature. The salient features of the present protocol are mild reaction conditions, short reaction time, high yields, operational simplicity, metal-free, applicability toward large-scale synthesis, and biodegradable and inexpensive catalyst.
