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.
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.
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.
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Appel,Siegemund
, p. 183,189 (1968)
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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.
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.
