139030-29-8Relevant articles and documents
An expeditious synthetic approach towards the synthesis of Bis-Schiff bases (aldazines) using ultrasound
Khan, Khalid M.,Jamil, Waqas,Ambreen, Nida,Taha, Muhammad,Perveen, Shahnaz,Morales, Guillermo A.
, p. 1200 - 1205 (2014)
Aldazines (Bis-Schiff bases) 1-24 were synthesized using aromatic aldehydes (heterocyclic and benzaldehydes) and hydrazine hydrate under reflux using conventional heating and/or via ultrasound irradiation using BiCl3 as catalyst. Ultrasonication conditions with cat. BiCl3 proved to be an effective, environmentally friendly synthetic procedure. This methodology is robust in the presence of electron donating and electron withdrawing groups affording desired products with high yields (>95%) in just a couple of minutes vs. hours using conventional heating.
A novel direct synthesis of (2,2-difluorovinyl)benzenes from aromatic aldehydes
Nenajdenko, Valentine G.,Varseev, Georgy N.,Korotchenko, Vasily N.,Shastin, Alexey V.,Balenkova, Elisabeth S.
, p. 115 - 118 (2003)
A novel catalytic approach to (2,2-difluorovinyl)benzenes has been developed. It was found that hydrazones of aromatic aldehydes generated in situ could be converted to the corresponding (2,2-difluorovinyl)benzenes by catalytic olefination reaction (COR) with dibromodifluoromethane in the presence of CuCl.
C[sbnd]N bond formation in alicyclic and heterocyclic compounds by amine-modified nanoclay
Zarnegar, Zohre,Alizadeh, Roghayeh,Ahmadzadeh, Majid,Safari, Javad
, p. 58 - 65 (2017)
In the current protocol, amine functionalized montmorillonite K10 nanoclay (NH2-MMT) was applied to catalyze the formation of C[sbnd]N bonds in the synthesis of azines and 2-aminothiazoles at room temperature. In comparison with the current methods of C[sbnd]N bond formation, this approach displays specific advantages include atom economy, clean conversion, design for energy efficiency, the use of nontoxic and heterogeneous catalyst, higher purity and yields, safer solvent and reagents for this organic transformation.
Charge-tansfer complexes of substituted aromatic azines and ?-acceptors
Mourad, Aboul-Fetouh E.
, p. 933 - 938 (1983)
Charge-transfer complexes of symmetrically substituted aromatic azines with tetracyanoethylene (TCNE) and 1,4-benzoquinones in methylene chloride have been investigated spectrophotometrically.The spectral data, molar extinction coefficients and transition energies of the complexes formed as well as the ionization potentials of the electron donors are reported.Both BENSI-HILDEBRAND and JOB methods have been applied in determination of association and apparent formation constants respectively.Substituent effect on charge-transfer equilibria of the substituted azines has been discussed.
Thermolysis of semicarbazones to the corresponding azines through reactive N-substituted isocyanate intermediates
Shah,Chudgar
, p. 657 - 664 (2000)
Thermolysis of semicarbazones (I) to azines (II) occurs through reactive N-substituted isocyanate intermediates (Ia) which can be converted in situ to carbamates and N-substituted ureas.
Tungsten hexachloride nanoparticles loaded on montmorillonite K-10: a novel solid acid catalyst in the synthesis of symmetrical and unsymmetrical azines
Safari, Javad,Gandomi-Ravandi, Soheila,Shariat, Saeedeh
, p. 1499 - 1507 (2016)
In the present investigation, we have developed a novel technique to prepare azines using nano-WCl6 loaded on Montmorillonite K10 clay as a highly active catalyst. A variety of aldehydes and ketones were efficiently converted to the corresponding azines using catalytic amounts of nanosized WCl6/Mont. K10 under mild conditions. The nanostructures of WCl6 loaded on Mont. K10 as solid acid catalyst have been prepared by solid dispersion method. The advantages of this catalyst are rapid completion of the reactions, simplicity of performance, lack of pollution and mild and green reaction conditions. The morphologies, structure, and chemical components of parent and modified clay were successfully characterized using SEM, FT-IR, CV, XRD and EDX measurements.
Selective and convenient protection of aldehydes as azines under solvent-free conditions
Eshghi, Hossein,Hosseini, Mosayyeb
, p. 636 - 638 (2008)
Aldehydes can be easily protected as azines in the presence of hydrazine monohydrochloride and ferric chloride under solvent-free conditions. The major advantages of this method are: operational simplicity, ready availability, selectivity, general applicability, mild reaction conditions with low cost of the reactants, short reaction times and excellent yields.
Ruthenium(ii)-catalysed 1,2-selective hydroboration of aldazines
Gunanathan, Chidambaram,Pradhan, Subham,Thiyagarajan, Subramanian
supporting information, p. 7147 - 7151 (2021/08/30)
Herein, an efficient and simple catalytic method for the selective and partial reduction of aldazines using ruthenium catalyst [Ru(p-cymene)Cl2]2 (1) has been accomplished. Under mild conditions, aldazines undergo the addition of pinacolborane in the presence of a ruthenium catalyst, which delivered N-boryl-N-benzyl hydrazone products. Notably, the reaction is highly selective, and results in exclusive mono-hydroboration and desymmetrization of symmetrical aldazines. Mechanistic studies indicate the involvement of in situ formed intermediate [{(η6-p-cymene)RuCl}2(μ-H-μ-Cl)] (1a) in this selective hydroboration.
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.
Non-Pincer-Type Arene Ru(II) Catalysts for the Direct Synthesis of Azines from Alcohols and Hydrazine under Aerobic Conditions
Saranya, Sundar,Ramesh, Rengan,Sémeril, David
, p. 3194 - 3201 (2020/09/15)
We report a tandem approach to synthesize symmetrical azines from alcohols and hydrazine hydrate catalyzed by synthesized arene Ru(II) complexes of aroylthiourea ligand. Notably, the catalytic efficiencies of six- and four-membered N,S-chelate ruthenium c
