4414-84-0Relevant academic research and scientific papers
One-pot solvent-free microwave-assisted aza-Michael addition reaction of acrylonitrile
Das, Parineeta,Devi, Nirmala,Puzari, Amrit
, (2022/03/23)
A novel and highly effective one-pot microwave-assisted aza-Michael addition reaction of acrylonitrile, as Michael acceptor with various primary aliphatic and aromatic amines, as Michael donor has been reported. The reaction was catalyzed by a cost-effective, highly efficient and eco-friendly catalyst, molecular sieve of 4 A0 size, under solvent-free conditions. A detail investigation on reaction controlling parameters like reaction timing and amount of catalyst was studied. The plausible mechanistic pathway has been proposed for the formation of acrylonitrile adducts. The identity of the synthesized products was established by conventional spectroscopic techniques FT-IR, 1H and 13C{1H} NMR, ESI-MS and DLS measurements. DLS result shows hydrodynamic diameter of lower alkyl chain in the range of 200–300 nm and for higher alkyl chain around 1 μm. Sheldon's hot filtration test confirms the significance of the catalyst and their heterogeneity was also confirmed by recycling it for five consecutive cycles without any noticeable change in the yield.
KOtBu-Catalyzed Michael Addition Reactions Under Mild and Solvent-Free Conditions
Thiyagarajan, Subramanian,Krishnakumar, Varadhan,Gunanathan, Chidambaram
supporting information, p. 518 - 523 (2020/02/04)
Designed transition metal complexes predominantly catalyze Michael addition reactions. Inorganic and organic base-catalyzed Michael addition reactions have been reported. However, known base-catalyzed reactions suffer from the requirement of solvents, additives, high pressure and also side-reactions. Herein, we demonstrate a mild and environmentally friendly strategy of readily available KOtBu-catalyzed Michael addition reactions. This simple inorganic base efficiently catalyzes the Michael addition of underexplored acrylonitriles, esters and amides with (oxa-, aza-, and thia-) heteroatom nucleophiles. This catalytic process proceeds under solvent-free conditions and at room temperature. Notably, this protocol offers an easy operational procedure, broad substrate scope with excellent selectivity, reaction scalability and excellent TON (>9900). Preliminary mechanistic studies revealed that the reaction follows an ionic mechanism. Formal synthesis of promazine is demonstrated using this catalytic protocol.
Synthesis, antifungal evaluation and molecular docking studies of some tetrazole derivatives
Afsarian, Mohammad Hosein,Farjam, Mojtaba,Zarenezhad, Elham,Behrouz, Somayeh,Rad, Mohammad Navid Soltani
, p. 874 - 887 (2020/01/21)
A facile and simple protocol for the [3+2] cycloaddition of alkyl nitriles (RCN) with sodium azide (NaN3) in the presence of copper bis(diacetylcurcumin) 1,2-diamin-obenzene Schiff base complex, SiO2-[Cu-BDACDABSBC] as a heterogeneous catalyst in the presence of ascorbic acid and a solution of water/i-PrOH (50:50, V/V) media at reflux condition is described. The supported catalyst was prepared by immobilization of a copper bis(diacetylcurcumin) 1,2-diaminobenzene Schiff base complex [Cu-BDACDABSBC] on silica gel. The complex has high selectivity, catalytic activity, and recyclability. The significant features of this procedure are high yields, broad substrate scope and simple and efficient work-up procedure. According to this synthetic methodology, excellent yields of 5-substituted 1H-tetrazoles having bioactive N-heterocyclic cores were synthesized. The in vitro antifungal activities of title compounds were screened against various pathogenic fungal strains, such as Candida species involving C. albicans, C. glabrata, C. krusei, C. parapsilosis as well as filamentous fungi like Aspergillus species consisting of A. fumigatus and A. flavus. The molecular docking analysis is discussed for one most potent compound against fungi. The docking study determined a remarkable interaction between the most potent compounds and the active site of Mycobacterium P450DM.
An efficient protocol for facile synthesis of new 5-substituted-1H-tetrazole derivatives using copper-doped silica cuprous sulfate (CDSCS) as heterogeneous nano-catalyst
Soltani Rad, Mohammad Navid
, p. 11 - 20 (2016/12/18)
A facile and highly efficient protocol for synthesis of new 5-substituted-1H-tetrazoles derivatives using copper-doped silica cuprous sulfate (CDSCS) is described. In this method, the cycloaddition reaction of sodium azide with structurally diverse nitriles involving bioactive N-heterocyclic cores exploiting CDSCS in refluxing H2O/i-PrOH (1:1, v/v) furnishes the corresponding 5-substituted-1H-tetrazoles in good to excellent yields (up to 93percent). The influence of parameters effective in progress of reaction including solvent type, temperature and catalyst was studied and discussed. In this protocol, CDSCS was proved to be an efficient heterogeneous nano-catalyst to easily achieve the new tetrazole derivatives. The advantages of CDSCS in current protocol known are its cheapness, thermal and chemical stability, ease of recyclability and reusability for several consecutive runs without significant decline in its reactivity.
Cu/Graphene/Clay Nanohybrid: A Highly Efficient Heterogeneous Nanocatalyst for Synthesis of New 5-Substituted-1H-Tetrazole Derivatives Tethered to Bioactive N-Heterocyclic Cores
Soltani Rad, Mohammad Navid,Behrouz, Somayeh,Sadeghi Dehchenari, Vahid,Hoseini, S. Jafar
, p. 355 - 365 (2017/02/03)
A series of new 5-substituted 1H-tetrazoles bearing bioactive N-heterocyclic cores were synthesized through [3 + 2] cycloaddition reactions between alkyl nitriles (RCN) and NaN3in the presence of Cu/aminoclay/reduced graphene oxide nanohybrid (Cu/AC/r-GO nanohybrid) as a heterogeneous nanocatalyst in water/i-PrOH (50:50, V/V) media at reflux condition. The influence of factors on a sample reaction including solvent type, temperature, and catalyst amount was discussed. This current protocol has many advantages including inexpensiveness, environmentally benign, broad substrate scope, excellent yields, and easy work-up procedure. The Cu/AC/r-GO used in this protocol is a low-cost catalyst that proved to have considerable chemical and thermal stabilities. This non-hygroscopic catalyst can be easily recycled, reused, and stored for many consecutive reaction runs without significant loss in its reactivity.
Ultrasound assisted synthesis of imidazolium salts: An efficient way to ionic liquids
Zbancioc, Gheorghita,Mangalagiu, Ionel I.,Moldoveanu, Costel
, p. 376 - 384 (2015/02/19)
In this study a straightforward and efficient approach concerning synthesis of 1,3-diazole derivatives under ultrasound (US) irradiation as well as under conventional thermal heating (TH) is presented. N-alkylation under US irradiation may be considered environmentally friendly in terms of higher yields, smaller amounts of solvent used and an overall energy efficiency due to a substantial reduction of reaction times. A comparative study of ultrasound vs. conventional conditions has been performed. Overall, the use of US proved to be more efficient than TH. A possible explanation concerning the different behavior of imidazole and benzimidazole in the N1-alkylation reactions under US irradiation was proposed.
Polystyrene-supported CuI-imidazole complex catalyst for aza-Michael reaction of imidazoles with α,β-unsaturated compounds
Li, Lixia,Liu, Zuliang,Ling, Qilong,Xing, Xiaodong
experimental part, p. 178 - 184 (2012/03/09)
The polystyrene-supported CuI-imidazole complex catalyst was prepared and characterized by IR spectroscopy, elemental analysis, SEM/TEM and TG/DSC. The complex catalyst was globular with the size of 400-500 nm and showed a good thermal stability at high temperature. The immobilized Cu metal in the complex catalyst was about 0.85 mmol/g. By using the catalyst, aza-Michael reaction of imidazoles to α,β-unsaturated compounds was performed with good yields in 4-8 h. The catalyst showed an excellent recycling efficiency over five cycles without distinct leaching of metal from the polymer support.
TREATING CARDIOVASCULAR DISEASES WITH N-(3-PHENOXY-2-HYDROXYPROPYL)BENZIMIDAZOLE-1-ALKANAMINES
-
, (2008/06/13)
3-Phenoxy-2-hydroxypropylamines having an N-benzimidazolyalkyl substituent and similar compounds are described herein. They are obtained by the reaction of the appropriate imidazole-1-alkanamine with an epoxide, and they are useful primarily as β 1-agonis
N-(3-PHENOXY-2-HYDROXYPROPYL)BENZIMIDAZOLE-1-ALKANAMINES
-
, (2008/06/13)
3-Phenoxy-2-hydroxypropylamines having an N-benzimidazolyalkyl substituent and similar compounds are described herein. They are obtained by the reaction of the appropriate imidazole-1-alkanamine with an epoxide, and they are useful primarily as β-adrenerg
