68175-07-5Relevant academic research and scientific papers
Access to 2-pyridinylamide and imidazopyridine from 2-fluoropyridine and amidine hydrochloride
Chen, Lu,Huang, Shuo,Ji, Xiaoliang,Li, Jiaming,Li, Jian,Li, Yibiao,Liu, Jiasheng,Peng, Shiyong,Zhang, Kun
supporting information, p. 9292 - 9299 (2020/12/03)
Under catalyst-free conditions, an efficient method to synthesize 2-pyridinylamides has been developed, and the protocol uses inexpensive and readily available 2-fluoropyridine and amidine derivatives as the starting materials. Simultaneously, the copper-catalysed approach to imidazopyridine derivatives has been established with high chemoselectivity and regiospecificity. The results suggest that the nitrogen-heterocycles containing iodide substituents can also be compatible for the reaction via the cascade Ullmann-type coupling, and the nucleophilic substitution reaction provides the target products in a one-pot manner.
Selective exploitation of acetoacetate carbonyl groups using imidazolium based ionic liquids: synthesis of 3-oxo-amides and substituted benzimidazoles
Chakraborty, Ankita,Majumdar, Swapan,Maiti, Dilip K.
, p. 3298 - 3302 (2016/07/11)
An unprecedented Br?nsted base ionic liquid tuned selective aminolysis of ester carbonyl of acetoacetates is demonstrated to achieve acetoacetamide derivatives. Other imidazolium ionic liquid performs an efficient cyclization catalysis involving acetoacetate-carbonyl groups and o-phenylenediamine at elevated temperature to produce benzimidazoles via C–C bond cleavage of intermediate 1,5-benzodiazepinones under solvent-free conditions.
Gadolinium (III) chloride catalyzed facile synthesis of 2-substituted benzimidazoles under solvent-free conditions
Sathaiah,Venkat Lingaiah,Chandra Shekhar,Ravi Kumar,Raju,Shanthan Rao
, p. 953 - 957 (2015/08/19)
A series of 2-substituted benzimidazoles have been prepared from o-diamines and 1,3-dicarbonyl compounds using Gadolinium chloride as a catalyst under solvent free condition in good yields. Gadolinium chloride has been demonstrated as a mild and efficient catalyst.
Studies on in vitro antimycobacterial activities of some 2-substitutedimidazo[4,5-b] and [4,5-c]pyridine derivatives
?zelik, Azime Berna,ülger, Mahmut,Aslan, G?nül,Emekda, Gürol,?zden, Tuncel
, p. 5 - 8 (2015/12/23)
In this study, 2-substitutedimidazo[4,5-b]pyridine and 2-substitutedimidazo[ 4,5-c]pyridine which have -CH2OH, -CH2Cl, -CH3 or -C2H5 groups in positions 2 have been synthesized and tested for their in vitro antimycobacterial activity against M. tuberculosis H37Rv strains. The compounds were synthesized by previously reported methods. 2-Chloromethylimidazo[4,5-b]pyridine and 2-methylimidazo[4,5-c]pyridine were found to be more active than the other compounds tested.
Novel strategy for synthesis of substituted benzimidazo[1,2-a]quinolines
Kato, Jun-Ya,Ito, Yutaro,Ijuin, Ryosuke,Aoyama, Hiroshi,Yokomatsu, Tsutomu
supporting information, p. 3794 - 3797 (2013/08/23)
An efficient method for the synthesis of benzimidazo[1,2-a]quinolines under transition-metal-free conditions has been developed through a cascade reaction involving sequential aromatic nucleophilic substitution and intramolecular Knoevenagel condensation reactions. This method is applicable for the synthesis of a wide range of benzimidazo[1,2-a]quinoline derivatives from readily available 2-fluoroarylaldehyde and benzimidazole substrates.
An efficient one-pot synthesis of condensed imidazoles using pentafluorophenylammonium triflate as novel, metal-free and reusable catalyst
Montazeri, Naser,Esmaeili, Abbas
, p. 3446 - 3448 (2013/05/21)
A superior method of synthesis of condensed imidazoles by the catalytic action of pentafluorophenylammonium triflate on the reaction of 1,2-diaminoaromatics with orthoesters is described. The catalyst is reusable and can be applied several times without considerable decrease in the yields and rates of the reaction.
Lithium bromide catalyzed solvent free method for synthesis of 2-substituted benzimidazoles and imidazopyridines
Dekhane, Deepak V.,Pawar, Shivaji S.,Gupta, Sunil V.,Shingare, Murlidhar S.,Thore, Shivaji N.
experimental part, p. 519 - 523 (2011/01/13)
The first successful lithium bromide mediated solvent free condensation of arylenediamine and esters to obtain 2-substituted benzimidazole and imidazopyridine in good to excellent yields is described.
Regioselective N-alkylation of imidazo[4,5-b]pyridine-4-oxide derivatives: an experimental and DFT study
Zeinyeh, Wael,Pilmé, Julien,Radix, Sylvie,Walchshofer, Nadia
scheme or table, p. 1828 - 1833 (2009/07/17)
Regioselectivities were determined for N-alkylations of imidazo[4,5-b]pyridine-4-oxide and 2-methyl-imidazo[4,5-b]pyridine-4-oxide with benzyl bromide or benzyl iodide at RT using K2CO3 in DMF as a base. Experimental attempts have shown that N-1/N-3 ratios slightly varied according to the substitution on C-2 position. This was confirmed by DFT calculations in solvent phase. This computational study has shown first that this N-benzylation reaction passed through a SN2 mechanism. Moreover, regioselectivity of N-benzylation has appeared essentially governed by 'steric approach control'. It explained that opposite N-1/N-3 ratios were obtained with imidazo[4,5-b]pyridine-4-oxide and its 2-methyl-substituted analog. Finally, regioselectivities slightly varied with the nature of benzyl halide.
SMALL MOLECULE INHIBITORS OF PLASMODIUM FALCIPARUM DIHYDROOROTATE DEHYDROGENASE
-
Page/Page column 39-40, (2010/01/29)
Inhibitors of dihydroorotate dehydrogenase (DHODH) for the Plasmodium enzyme have been identified and characterized. The inhibitors have high specificity, submicromolar efficacy against cultured parasite strains, exhibit drug-like properties, and are not overtly cytotoxic.
