1856-33-3Relevant academic research and scientific papers
Fe3O4@L-lysine-Pd(0) organic–inorganic hybrid: As a novel heterogeneous magnetic nanocatalyst for chemo and homoselective [2 + 3] cycloaddition synthesis of 5-substituted 1H-tetrazoles
Ashraf, Muhammad Aqeel,Liu, Zhenling,Li, Cheng,Zhang, Dangquan
, (2020/12/23)
An efficient and sustainable synthetic protocol has been presented to synthesis and 5-substituted 1H-tetrazole privileged heterocyclic substructures. The synthetic protocol involves two-component reaction between aryl nitriles and NaN3 in water using complex of L-lysine-palladium nanoparticles (NPs) modified Fe3O4 nanoparticles as magnetically separable, recyclable, and reusable heterogeneous catalyst. Magnetically retrievable L-lysine-Pd(0) modified Fe3O4 nanoparticles were applied in [2 + 3] cycloaddition synthesis of 5-substituted 1H-tetrazoles. The advantages of this strategy include easy recovery and efficient reusability of the expensive Pd NPs, obtaining high yields of [2 + 3] cycloaddition, short reaction times, and all of the reported synthetic strategies are being performed in water as green solvent for a wide range of substrates.
Igneous rock powder as a heterogeneous multi-oxide nano-catalyst for the synthesis of 5-substituted-1H-tetrazoles in polyethylene glycol
Javaherian, Mohammad,Movaheditabar, Parviz,Nobakht, Valiollah
, (2021/10/25)
The use of igneous rock nano-powder as a heterogeneous and recyclable multi-oxide nano-catalyst synthesizing of 5-substituted-1H-tetrazoles is reported. The igneous rock nano-powder was initially prepared by using the ball-milling method. Then, the structure, morphology, and magnetic properties of the prepared igneous rock nano-powder were characterized with some different spectroscopic, microscopic, and thermogravimetric techniques, such as FTIR, FESEM, XRF, XRD, Histogram, and EDS. The instrumental analyses showed that the prepared igneous rock powder is a mixture of metal oxides, such as Si, Al, Ca, Mg, Fe, Na, Mn, and Sr. It showed an excellent catalytic performance in synthesizing of 5-substituted-1H-tetrazoles through [3 + 2] cycloaddition reaction between sodium azide and nitrile compounds. Various aliphatic and aromatic nitriles and sodium azide were reacted in the presence of a catalytic amount of igneous rock nano-powder at 80 o C temperature in PEG-400. The protocol was simple and rapid, with suitable yields of the obtained tetrazoles. The igneous rock nano-powder is readily accessible, reusable, and holds potential for further application in acid-catalyzed organic syntheses and industrial requirements. Graphic abstract: [Figure not available: see fulltext.]
Synthesis of 5-Substituted 1 H-Tetrazoles from Nitriles by Continuous Flow: Application to the Synthesis of Valsartan
Carpentier, Florian,Felpin, Fran?ois-Xavier,Zammattio, Fran?oise,Le Grognec, Erwan
, p. 752 - 761 (2020/03/13)
An efficient continuous flow process for the synthesis of 5-substituted 1H-tetrazoles is described. The process involves the reaction between a polymer-supported triorganotin azide and organic nitriles. The polymer-supported organotin azide, which is in situ generated with a polystyrene-supported triorganotin alkoxide and trimethylsilylazide, is immobilized in a packed bed reactor. This approach is simple, fast (it takes from 7.5 to 15 min), and guarantees a low concentration of tin residues in the products (5 ppm). The process was developed to aryl-, heteroaryl-, and also alkylnitriles and was applied for the synthesis of valsartan, an angiotensin II receptor antagonist.
Efficient synthesis of tetrazole hemiaminal silyl ethers via three-component hemiaminal silylation
Xie, Ming-Sheng,Cheng, Xuan,Chen, Yang-Guang,Wu, Xiao-Xia,Qu, Gui-Rong,Guo, Hai-Ming
supporting information, p. 6890 - 6894 (2018/10/17)
An efficient route to construct 2,5-disubstituted tetrazole hemiaminal silyl ethers via one-pot three-component hemiaminal silylation of 5-substituted tetrazoles, aldehydes, and silyl triflates was developed. Diverse 2,5-disubstituted tetrazole hemiaminal silyl ethers were obtained with 37?:?63->99?:?1 regioisomeric ratios. The regioselectivities of this reaction were significantly affected by steric hindrance and the conjugation effects of substitutions on the 5-position of tetrazoles.
Indium-, Magnesium-, and Zinc-Mediated Debenzylation of Protected 1 H -Tetrazoles: A Comparative Study
Behloul, Cherif,Benlahrech, Meriem,Foubelo, Francisco,Nájera, Carmen,Yus, Miguel
supporting information, p. 3430 - 3435 (2018/07/02)
5-Substituted 1-benzyltetrazoles are easily debenzylated to give the corresponding deprotected tetrazoles using dissolved metals under protic conditions: Mg/MeOH, In/MeOH, or Zn/MeCO 2 H are the procedures of choice for this transformation.
Design, synthesis and in vitro activity of 1,4-disubstituted piperazines and piperidines as triple reuptake inhibitors
Paudel, Suresh,Acharya, Srijan,Yoon, Goo,Kim, Kyeong-Man,Cheon, Seung Hoon
, p. 2266 - 2276 (2017/03/23)
Monoamine transporters regulate the concentration of monoamine neurotransmitters, which are essential for vital physiological processes, and their dysfunction can cause several central nervous system diseases. Monoamine transporters currently appear to be the potential target in the management of these disorders. In this study, homologation and bioisosterism techniques have been used in the designing of new 1,4-disubstituted piperazines and piperidines. These derivatives were synthesized and evaluated as potential triple reuptake inhibitors for studying the structure-activity relationships. The most advanced compound, 1-(4-(5-benzhydryl-1H-tetrazol-1-yl)butyl)-4-(3-phenylpropyl)piperazine (2i), was able to inhibit monoamine neurotransmitter reuptake in an in vitro test (IC50?=?158.7?nM for 5-HT, 99?nM for NE and 97.5?nM for DA). These novel potent triple reuptake inhibitor-based 1,4-disubstituted piperazine and piperidine scaffolds deserve further systematic optimization and pharmacological evaluation.
Design, synthesis and evaluation of 5-substituted 1-H-tetrazoles as potent anticonvulsant agents
Liao, Ai-Mei,Wang, Tiantian,Cai, Bangrong,Jin, Yi,Cheon, Seunghoon,Chun, Chang Ju,Wang, Zengtao
, p. 435 - 443 (2017/04/13)
Abstract: A series of 5-substituted 1-H-tetrazoles were designed and synthesized as potent anticonvulsant agents. Their preliminary anticonvulsant activities were evaluated using maximal electroshock and subcutaneous pentylenetetrazole (scPTZ) seizure tests. Neurotoxicity was determined using rotarod test. The results indicated that the compound 2j in scPTZ model exhibited the ED50 values of 83.3?mg/kg, superior to the standard drug ethosuximide with the maximum activity. In addition, compound 2k showed the most potent activity in MES model with ED50 value of 9.6?mg/kg and TD50 value of 189.5?mg/kg after intraperitoneal injection in mice, and displayed a high protective index (TD50/ED50) of 19.7 compared to reference antiepileptic drugs. Graphical Abstract: [Figure not available: see fulltext.]
Zn/MeOH-Mediated Practical and Easy Detritylation of Protected 1-Trityltetrazoles
Behloul, Cherif,Bouchelouche, Kenza,Hadji, Yasmine,Benseghir, Saadia,Guijarro, David,Nájera, Carmen,Yus, Miguel
supporting information, p. 2455 - 2460 (2016/07/28)
A practical and low-cost method for the detritylation of 1-titryltetrazoles using zinc and methanol is described. This procedure is versatile and efficient in the deprotection of several protected tetrazoles bearing aliphatic, aromatic, and heteroaromatic substituents, as well as some functional groups, without decomposition of the tetrazole ring.
Exploration of substituted arylpiperazine–tetrazoles as promising dual norepinephrine and dopamine reuptake inhibitors
Paudel, Suresh,Acharya, Srijan,Yoon, Goo,Kim, Kyeong-Man,Cheon, Seung Hoon
, p. 5546 - 5555 (2016/10/22)
In the search for potent dual norepinephrine and dopamine reuptake inhibitors, several substituted arylpiperazine–tetrazoles were designed, synthesized and evaluated for their neurotransmitter reuptake inhibitory activities. Various derivatives exhibited selective and strong neurotransmitter reuptake inhibitory activity. In particular, compounds with a three-carbon linker displayed selective and stronger potency than those with two-carbon and four-carbon linkers. Interestingly, six compounds, 9b, 9c, 9d, 9o, 9q and 9u displayed more effective activity than the standard drug, bupropion. The provided SAR data and potent biological activity can offer useful guidelines for designing dual norepinephrine and dopamine reuptake inhibitors as effective therapeutic agents for treatment of several central nervous system diseases.
