5332-26-3Relevant academic research and scientific papers
Synthesis method N - bromomethylphthalimide
-
Paragraph 0015-0027, (2021/09/21)
The invention discloses a synthesis method N -bromomethylphthalimide, which uses N - hydroxymethyl phthalimide in an inert solvent and bromination reaction of phosphorus tribromide to obtain N -bromomethylphthalimide. To the invention, the reaction is complete by equimolar or slightly excess phosphorus tribromide, the utilization rate of the raw material bromine atom is greatly improved, the three-waste emission is reduced, the production efficiency is improved, and the production cost is reduced. The mother liquor can be directly sheathed into the next batch of feeding. The by-product phosphorous acid is sold as a byproduct, the process itself realizes zero release, and the sustainable development direction of clean production is represented.
Design, Synthesis, Molecular Docking, and Cholinesterase Inhibitory Potential of Phthalimide-Dithiocarbamate Hybrids as New Agents for Treatment of Alzheimer's Disease
Asadi, Mehdi,Ebrahimi, Mostafa,Mohammadi-Khanaposhtani, Maryam,Azizian, Homa,Sepehri, Saghi,Nadri, Hamid,Biglar, Mahmood,Amanlou, Massoud,Larijani, Bagher,Mirzazadeh, Roghieh,Edraki, Najmeh,Mahdavi, Mohammad
, (2019/11/11)
A novel series of phthalimide-dithiocarbamate hybrids was synthesized and evaluated for in vitro inhibitory potentials against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The anti-cholinesterase results indicated that among the synthesized compounds, the compounds 7g and 7h showed the most potent anti-AChE and anti-BuChE activities, respectively. Molecular docking and dynamic studies of the compounds 7g and 7h, respectively, in the active site of AChE and BuChE revealed that these compounds as well interacted with studied cholinesterases. These compounds also possessed drug-like properties and were able to cross the BBB.
Synthesis and Characterization of Novel Phthalimide-pyrano[3,2-c]chromene and Phthalimide-pyrano-2-one Hybrids
Sameem, Bilqees,Saeedi, Mina,Mahdavi, Mohammad,Nadri, Hamid,Vafadarnejad, Fahimeh,Amini, Mohsen
, p. 1678 - 1684 (2018/06/04)
Coumarin skelton holds substantial promise for further exploration because of its immense pharmacological potential. In this pursuit, a series of phthalimide-chromen and phthalimide-pyran-2-one hybrids were synthesized in efficient yields via one-pot multicomponent reaction of aldehyde linked to phthalimide moiety, 4-hydroxy coumarin/4-hydroxy-6-methyl-2H-pyran-2-one, and malanonitrile by Knoevenagel reaction at room temperature in the presence of DABCO as catalyst. The compounds were characterized by 1H NMR and 13C NMR, MS, and FTIR. All the compounds consisting of phthalimide-chromen/pyrano-2-one moieties tethered by spacers of varying lengths were evaluated for their biological activity in Ellman's assay. Most of the compounds feebly inhibited Acetylcholinesterase Enzyme and were inactive toward Butyrylcholinesterase Enzyme.
Elucidating the Reaction Pathway of Decarboxylation-Assisted Olefination Catalyzed by a Mononuclear Non-Heme Iron Enzyme
Yu, Cheng-Ping,Tang, Yijie,Cha, Lide,Milikisiyants, Sergey,Smirnova, Tatyana I.,Smirnov, Alex I.,Guo, Yisong,Chang, Wei-Chen
supporting information, p. 15190 - 15193 (2018/11/23)
Installation of olefins into molecules is a key transformation in organic synthesis. The recently discovered decarboxylation-assisted olefination in the biosynthesis of rhabduscin by a mononuclear non-heme iron enzyme (P.IsnB) represents a novel approach in olefin construction. This method is commonly employed in natural product biosynthesis. Herein, we demonstrate that a ferryl intermediate is used for C-H activation at the benzylic position of the substrate. We further establish that P.IsnB reactivity can be switched from olefination to hydroxylation using electron-withdrawing groups appended on the phenyl moiety of the analogues. These experimental observations imply that a pathway involving an initial C-H activation followed by a benzylic carbocation species or by electron transfer coupled β-scission is likely utilized to complete C=C bond formation.
Synthesis, structural and antioxidant studies of some novel N-ethyl phthalimide esters
Kumar, C.S. Chidan,Loh, Wan-Sin,Chandraju, Siddegowda,Win, Yip-Foo,Tan, Weng Kang,Quah, Ching Kheng,Fun, Hoong-Kun
, (2015/05/27)
A series of N-ethyl phthalimide esters 4(a-n) were synthesized and characterized by spectroscopic studies. Further, the molecular structure of majority of compounds were analysed by single crystal X-ray diffraction studies. The X-ray analysis revealed the importance of substituents on the crystal stability and molecular packing. All the synthesized compounds were tested for in vitro antioxidant activity by DPPH radical scavenging, FRAP and CUPRAC methods. Few of them have shown good antioxidant activity.
A novel and efficient route for the preparation of atorvastatin
Gao, Jian,Guo, Yang Hui,Wang, Ya Ping,Wang, Xiang Jing,Xiang, Wen Sheng
scheme or table, p. 1159 - 1162 (2012/01/16)
A novel and efficient synthetic method of atorvastatin was described. The key step of the synthesis was the construction of the olefin linkage between the chiral side chain and skeleton via a Horner-Wadsworth-Emmons reaction, resulting in the advanced intermediate of atorvastatin under hydrogenation of the olefin over Pd/C. This novel method is more useful for the practical synthesis of atorvastatin than its document reported methods.
Convenient routes to trifluoromethyl-substituted pyridyl-isothiocyanates and isocyanates starting from 2,3-dichloro-5-trifluoromethyl pyridine
Fodor, Elena,Maftei, Catalin-Vasile,Mangalagiu, Ionel,Jones, Peter G.,Daniliuc, Constantin-Gabriel,Franz, M. Heiko,Neda, Ion
scheme or table, p. 559 - 564 (2011/08/22)
A convenient preparative route for the synthesis of 3-chloro-2- (isothiocyanatoethyl)-5-(trifluoromethyl)pyridine (1) and 3-chloro-2- (isocyanatoethyl)-5-(trifluoromethyl)pyridine (2) has been developed, involving 5 steps starting from 2, 3-dichloro-5-(trifluoromethyl)pyridine (3). All intermediates and final products were obtained in good yields and purity. The structure of one intermediate, 2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl) malonate, was confirmed by X-ray crystallography.
Phosphonate diester and phosphonamide synthesis. Reaction coordinate analysis by 31P NMR spectroscopy: Identification of pyrophosphonate anhydrides and highly reactive phosphonylammonium salts
Hirschmann, Ralph,Yager, Kraig M.,Taylor, Carol M.,Witherington, Jason,Sprengeler, Paul A.,Phillips, Barton W.,Moore, William,Smith III, Amos B.
, p. 8177 - 8190 (2007/10/03)
A series of phosphonochloridates was prepared from the corresponding phosphonate monoesters, and their reactions with alcohols, amines, and the bisnucleophile 4-aminobutan-1-ol have been investigated using 31P NMR spectroscopy. In the conversion of phosphonate monoesters to phosphonochloridates via the addition of thionyl chloride or oxalyl chloride, pyrophosphonate anhydrides were found to be formed readily as byproducts. The anhydrides reacted readily with alcohols, but more slowly than the corresponding phosphonochloridates, and only sluggishly, if at all, with amines. Therefore, when phosphonamides are prepared, anhydride formation must be suppressed. This is accomplished when the monoester is added to the chloridating agent. Unhindered phosphonochloridates reacted predominantly with the amino function of 4-aminobutan-1-ol to furnish the phosphonamidates, whereas a sterically hindered phosphonochloridate demonstrated a preference for O-coupling. This result indictes that the energy gained during P-O bond formation surmounts the kinetic barrier resulting from steric hindrance more effectively than formation of the weaker P-N bond. Importantly, treatment of the phosphonochloridates with tertiary amines prior to addition of the nucleophile resulted in the formation of hitherto unrecognized phosphonylating agents, which we formulated as phosphonyltrialkylammonium salts. The latter, unlike the anhydrides, are more reactive than the phosphonochloridates toward both alcohols and amines, affording improved yields of phosphonate esters and amides. These improved yields are not obtained when triethylamine is added simultaneously with the nucleophile merely to neutralize acid rather than as a deliberate step to generate the phosphonyltrialkylammonium salts. Use of these novel phosphonylating agents proceeded without concomitant racemization at stereogenic centers α to phosphorous. Interestingly, reaction of even an unhindered phosphonyltriethylammonium salt with 4-aminobutan-1-ol favored O-phosphonylation over N-phosphonylation by a factor of 8, demonstrating that both the charge transfer in the transition state and steric hindrance affect the propensity for P-O vis a vis P-N bond formation. In marked contrast, simultaneous addition of this bisnucleophile and triethylamine, like coupling in the absence of tertiary amine, afforded the phosphonate and phosphonamide in nearly equal amounts.
Stereoelectronic effects in the halogenation of N-alkylnaphthalimides
Easton, Christopher J.,Scharfbillig, Ilse M.,Tiekink, Edward R. T.
, p. 5613 - 5616 (2007/10/02)
The greater rate of bromination of N-methylnaphthalimide compared to N-ethylnaphthalimide, and the relative ease of chlorination of these compounds, provide convincing evidence of stereoelectronic effects in the free-radical halogenation of N-alkylimides.
A PRACTICAL SYNTHESIS OF α-AMINOPHOSPHONIC ACIDS
Genet, J. P.,Uziel, J.,Port, M.,Touzin, A. M.,Roland, S.,et al.
, p. 77 - 80 (2007/10/02)
The preparation of diterbutyl-N (diphenylmethylene) aminomethylphosphonate 3 in four steps (42percent overall yield) from N-hydroxymethyl phthalimide 1 is described.Various α substituted α-aminophosphonic acids 5 containing functionalized unsaturated chains have been synthesized by alkylation of 3 under phase transfer catalysis with halides, Michael acceptors and palladium promoted reactions, followed by mild hydrolysis. Key words: Schiff bases of diterbutylaminomethylphosphonate; phase transfer catalysis; palladium-catalyzed allylic substitution; Michael additions.
