34442-94-9Relevant articles and documents
“On water” nano-Cu2O-catalyzed CO-free one-pot multicomponent cascade cyanation-annulation-aminolysis reaction toward phthalimides
Wen, Xiaowei,Liu, Xiaojuan,Yang, Zhiqi,Xie, Menglan,Liu, Yuxi,Long, Lipeng,Chen, Zhengwang
supporting information, p. 1738 - 1743 (2021/03/14)
An efficient nano-Cu2O-catalyzed cascade multicomponent reaction of 2-halobenzoic acids and trimethylsilyl cyanide with diverse amines was developed using water as a solvent, affording versatileN-substituted phthalimide derivatives in moderate to excellent yields. This novel strategy features carbon monoxide gas-free, environmentally benign, one-pot multistep transformation, commercially available reagents, a cheap catalyst without any additives, wide functional group tolerance, and operational convenience.
The aminocarbonylation of 1,2-diiodoarenes with primary and secondary amines catalyzed by palladium complexes with imidazole ligands
Wójcik, Przemys?aw,Trzeciak, Anna M.
, p. 73 - 83 (2018/05/22)
The efficient carbonylative cyclization of 1,2-diiodobenzene with different primary and secondary amines was performed using a palladium complex with an imidazole ligand, PdCl2(BIM)2, as a catalyst. In reactions performed at 1 atm of CO with primary amines, phthalimides were obtained as the only products with yields of up to 100% in 4 h. An even shorter time, 1 h, was sufficient to obtain the same products employing methyl-2-iodobenzoate as a substrate instead of 1,2-diiodobenzene. In an analogous reaction with secondary amines, 1,2-diiodobenzene was converted to three products, formed in amounts dependent on the reaction conditions. The presence of Pd NPs and soluble palladium intermediates indicated their participation in the catalytic reaction.
Synthesis and antiseizure evaluation of isoindoline-1,3-dione derivatives in mice
Aliabadi, Alireza,Gholamine, Babak,Karimi, Tahereh
, p. 2736 - 2743 (2014/05/06)
Epilepsy is the most common serious chronic noninfective neurological condition in the world. Despite the presence of various antiepileptic drugs in the market for epileptic patients, the necessity for development and discovery of novel antiepileptic drugs is felt. In fact, only 60-70 % of patients respond to the current drugs, and a high incidence of adverse effects is also observed. In the present study, a new series of phthalimide derivatives (compounds 3a-3m) were synthesized through the reaction of phthalic anhydride and various derivatives of aniline in toluene solvent (Reflux, 24 h). Antiepileptic activity of synthesized compounds (3a-3m) was investigated using two experimental models namely, maximal electroshock (MES) and pentylenetetrazole (PTZ), and the obtained results were compared with diazepam as reference drug. Neurotoxicity of compounds was also evaluated using rotarod model. Compound 3m with para methoxy substituent exhibited the anticonvulsant activity at 15.1 ± 1.53 (12.23-17.96) mg/kg dose in MES model compared to other derivatives. Unfortunately, none of the tested compounds rendered acceptable protection in subcutaneous PTZ model.
Aza-DielsAlder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome
Jha, Amitabh,Chou, Ting-Yi,ALJaroudi, Zainab,Ellis, Bobby D.,Cameron, T. Stanley
, p. 848 - 857 (2014/05/06)
The synthesis of 5-substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)- ones via [4 + 2] imino-DielsAlder cyclization from N-aryl-3- hydroxyisoindolinones and N-vinyl lactams under Lewis acid-catalysed anhydrous conditions is reported. Reactions of N-(2-substituted-aryl)-3- hydroxyisoindolinones with N-vinylpyrrolidone under identical conditions resulted in the formation of 2-(2-substitued-aryl)-3-(2-(2-oxopyrrolidin-1-yl) vinyl)isoindolin-1-one analogues indicating steric hinderance as the cause of deviation. The probable mechanism of the reaction based on the results from X-ray crystallography and molecular modelling is discussed.
Docking, synthesis, and pharmacological evaluation of isoindoline derivatives as anticonvulsant agents
Davood, Asghar,Amini, Mohsen,Azimidoost, Leila,Rahmatpour, Somaieh,Nikbakht, Ali,Iman, Maryam,Shafaroodi, Hamed,Ansari, Abdollah
, p. 3177 - 3184 (2013/07/19)
Eleven analogs of N-arylisoindoline pharmacophore were synthesized and evaluated for their anticonvulsant activities. The in vivo screening data acquired indicate that all the analogs have the ability to protect against pentylenetetrazole-induced seizure. Compounds 2, 6, and 11 elevated clonic seizure thresholds at 30 min which were more active than reference drug phenytoin, and compounds 2, 7, and 11 showed marked anticonvulsant activity on tonic seizure. The most potent compounds were 2 and 11 which had comparative activity to the phenytoin. Using a model of the open pore of the Na channel, we have docked all compounds. Docking studies have revealed that these compounds interacted mainly with residues II-S6 of NaV1.2 by making hydrogen bonds and have additional hydrophobic interactions with other domains in the channel's inner pore.
Iron(II) bromide-catalyzed synthesis of benzimidazoles from aryl azides
Shen, Meihua,Driver, Tom G.
supporting information; experimental part, p. 3367 - 3370 (2009/05/27)
(Chemical Equation Presented) The identity of the ortho-substituent of an aryl azide influences its reactivity toward transition metals. Substitution of a vinyl group with an imine disables rhodium(II)-mediated C-H amination and triggers a Lewis acid mechanism catalyzed by iron(II) bromide to facilitate benzimidazole formation.
Pharmaceutical uses and synthesis of nicotinamides
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Page/Page column 25, (2010/02/08)
A compound of the formula and pharmaceutically acceptable salts thereof, wherein R1is selected from (R3)C(═O)—N(R4)— and (R3)(R4)N—C(═O)—; R2is selected from —OR5and —N(R5)(R6); n is 0, 1, 2 or 3; X is selected from oxygen and sulfur; and R3, R4, R5and R6are independently selected from hydrogen, alkyl, heteroalkyl, aryl, aryl(akylene), heteroaryl, heteroaryl(alkylene), carbocycle, carbocycle(alkylene), heterocycle, and heterocycle(alkylene); as well as pharmaceutical compositions containing said compound. The compounds and compositions are useful in, for example, the treatment of inflammatory events in an animal subject.
Kinetic versus thermodynamic access to imidazoisoindolones, benzimidazoisoindolones, and [1,4]diazepinoisoindolones: Intramolecular nitrogen and π-aromatic trapping of N-acyliminium cation
Cul, Armelle,Da?ch, Adam,Decroix, Bernard,Sanz, Gérard,Van Hijfte, Luc
, p. 11029 - 11039 (2007/10/03)
Efficient assembly of substituted imidazo[2,1-a]isoindolones I is reported from suitable α,β-diamine IV (or corresponding β-nitroamine) and phthalic anhydride (1) in a three- or four-step sequence in good yields. The key step of this methodology is based on an intramolecular α-aza- amidoalkylation of the N-acyliminium species. Furthermore, when R2 is an aromatic moiety a competing α-amidoalkylation took place and imidazo[2,1-a]isoindolones (or benzimidazo[2,1-a]isoindolones) I and/or isoindolo[1,4]benzodiazepines III were obtained under kinetic or thermodynamic control. The chemoselectivity of these transformations is also discussed.
Protection of amino group as N-phthalyl derivative using microwave irradiation
Khadilkar, Bhushan M.,Madyar, Virendra R.
, p. 1083 - 1085 (2007/10/03)
The amino groups for various substrates are protected as N-phthalyl derivatives using solvent free neat condition under microwave exposure.
