33511-74-9Relevant academic research and scientific papers
Convenient one-pot synthesis of multisubstituted tetrahydropyrimidines via catalyst-free multicomponent reactions
Zhang, Min,Jiang, Huanfeng,Liu, Hailing,Zhu, Qiuhua
, p. 4111 - 4113 (2007)
A novel and convenient one-pot synthesis of multisubstituted pyrimidine analogues via multicomponent reactions is disclosed. This catalyst-free domino reaction proceeded smoothly in good to excellent yields and offered several other advantages including short reaction time, a simple experimental workup procedure, and no toxic byproduct. In addition, the obtained products in our experiments are interesting nitrogen heterocyclic molecules containing α- and β-amino acid blocks.
One-Pot Synthesis of Benzo[4,5]imidazo[1,2-a]pyrimidin-2-ones Using a Hybrid Catalyst Supported on Magnetic Nanoparticles in Green Solvents
Moussa, Alkassoume,Rahmati, Abbas
, p. 764 - 774 (2021/08/30)
The conversion of soluble polyoxometalate into insoluble polyoxometalate is considered to be one of the major challenges in synthetic organic chemistry. Here, polyoxometalate was bonded to the salt part of an organic branch immobilized on the silica-coate
Substituent-controlled chemoselective synthesis of multi-substituted pyridones: Via a one-pot three-component cascade reaction
Liu, Shitao,Li, Jisen,Lin, Junjie,Liu, Fujun,Liu, Teng,Huang, Chao
, p. 1130 - 1134 (2020/02/22)
An efficient and concise one-pot strategy for the synthesis of multisubstituted pyridones via a one-pot three-component cascade reaction catalyzed by Cs2CO3 under solvent-free conditions has been developed. The substituent-controlled chemoselective cycloaddition process involved steps including a Michael addition/ethanol elimination/intermolecular cyclization sequence utilizing anilines, diethyl acetylenedicarboxylate, and diethyl ethoxymethylenemalonate. In doing so, various 2-pyridone and 4-pyridone species (41 examples) could be obtained in good to excellent yields.
Stereoselective Aminoiodination of Activated Alkynes with Organoiodine(III) Reagents and Amines via Multiple-Site Functionalization: Access to Iodinated Enamines and N-Aryl Indoles
Arepally, Sagar,Chamuah, Ajoy,Katta, Narenderreddy,Sharada, Duddu S.
supporting information, p. 1542 - 1547 (2019/02/03)
A stereoselective aminoiodination of activated alkynes with PhI(OAc)2 and amines via multiple-site functionalization to afford (Z)diethyl 2-(diphenylamino)-3-iodomaleate derivatives with superior yields has been described. The key feature of th
Novel One-Pot Synthesis of Functionalized Quinolines from Isocyanides, Aniline, and Acetylene Dicarboxylate via Cu-Catalyzed Intramolecular C─H Activation Reactions
Nematpour, Manijeh,Rezaee, Elham,Jahani, Mehdi,Tabatabai, Sayyed Abbas
, p. 1254 - 1259 (2019/03/07)
The one-pot synthesis of a novel class of substituted quinoline derivatives with good yields is achieved via the Cu-catalyzed intramolecular C─H activation reaction between isocyanides, aniline, and acetylene dicarboxylate in MeCN at room temperature. The
Structural evaluation and electrophysiological effects of some kynurenic acid analogs
Fehér, Evelin,Szatmári, István,Dudás, Tamás,Zalatnai, Anna,Farkas, Tamás,Orinczi, Bálint L.,Fül?p, Ferenc,Vécsei, László,Toldi, József
, (2019/10/02)
Kynurenic acid (KYNA), a metabolite of tryptophan, as an excitatory amino acid receptor antagonist is an effective neuroprotective agent in case of excitotoxicity, which is the hallmark of brain ischemia and several neurodegenerative processes. Therefore, kynurenine pathway, KYNA itself, and its derivatives came into the focus of research. During the past fifteen years, our research group has developed several neuroactive KYNA derivatives, some of which proved to be neuroprotective in preclinical studies. In this study, the synthesis of these KYNA derivatives and their evaluation with divergent molecular characteristics are presented together with their most typical effects on the monosynaptic transmission in CA1 region of the hippocampus of the rat. Their effects on the basic neuronal activity (on the field excitatory postsynaptic potentials: fEPSP) were studied in in vitro hippocampal slices in 1 and 200 μM concentrations. KYNA and its derivative 4 in both 1 and 200 μM concentrations proved to be inhibitory, while derivative 8 only in 200 μM decreased the amplitudes of fEPSPs. Derivative 5 facilitated the fEPSPs in 200 μM concentration. This is the first comparative study which evaluates the structural and functional differences of formerly and newly developed KYNA analogs. Considerations on possible relations between molecular structures and their physiological effects are presented.
Trifluoroacetic acid catalyzed one-pot four-component domino reaction for the synthesis of substituted dihydro 2-oxypyrroles
Lashkari, Mojtaba,Maghsoodlou, Malek Taher,Karima, Mahsa,Kangani, Mehrnoosh
, p. 3799 - 3802 (2018/05/24)
Trifluoroacetic acid was applied as an effcient catalyst for the one-pot four-component synthesis of N-aryl/alkyl-3-aminodihydropyrrol-2-one-4-carboxylates via the domino reaction of amines, formaldehyde and dialkyl acetylenedicarboxylates at ambient temp
Chemoselective Nitrosylation of Anilines and Alkynes via Fragmentary or Complete NO Incorporation
Pan, Jun,Li, Xinyao,Lin, Fengguirong,Liu, Jianzhong,Jiao, Ning
supporting information, p. 1427 - 1442 (2018/04/20)
The cycloaddition reactions have been explored extensively and provided an efficient strategy for the synthesis of cyclic compounds. Traditionally, the reaction partners were in extenso incorporated into the cyclic products without fragmentation. From a different perspective, if certain fragmentations via chemical-bond cleavage are involved in this cycloaddition reaction, it would change the assembly sequence and enable more product diversity. Here, we report a chemoselective nitrosylation of anilines and alkynes through fragmentary or complete NO radical incorporation. The formation of multiple C–N bonds, an unexpected C–N bond, and N=O bond cleavage make this fragmentary cycloaddition reaction an efficient approach to 2,5-dihydrooxazoles, 1H-1,2,3-triazole 2-oxides or quinoxaline N-oxides. Facile operation in open-air, metal-free, and mild conditions renders this protocol particularly practical and attractive. A series of mechanistic studies and density functional theory calculations were also conducted, which help to explain the fragmentary or complete NO incorporation processes, broadening the field of new reaction discovery. Exploring novel structures and developing convenient and direct methods to achieve them are an essential issue in synthetic chemistry. In traditional cycloaddition reactions, the reaction partners are in extenso incorporated into the cyclic compound products. In contrast, the fragmentary incorporation of the reaction partners via chemical-bond cleavage in cycloaddition reactions would change the assembly sequence and enable more product diversity. However, fragmentary incorporation in cycloaddition reactions remains a challenging issue because of the high bond-dissociation energy and poor selectivity. This paper reports a fragmentary cycloaddition reaction that enables a series of new structures through a controllable radical process. This work also reveals the diversity of transformation of free radical intermediates. The accessible products might also trigger some interest in pharmaceutical science and materials science. Cycloaddition reactions provide an efficient strategy for the synthesis of cyclic compounds and have been well developed. However, cycloaddition reactions with fragmentary partner incorporation via the cleavage of multiple bonds, which allows for more structural diversity than traditional cycloaddition reactions, have seldom been reported. Here, we describe a chemoselective nitrosylation of anilines and alkynes through fragmentary or complete NO radical incorporation for an efficient approach to 2,5-dihydrooxazoles, 1H-1,2,3-triazole 2-oxides, or quinoxaline N-oxides.
A three-component one-pot synthesis of penta-substituted pyrroles via ring opening of α-nitroepoxides
Zhao, Donghong,Zhu, Yue,Guo, Shanshan,Chen, Wenteng,Zhang, Guolin,Yu, Yongping
supporting information, p. 2872 - 2877 (2017/04/26)
A novel and facile one-pot reaction has been developed to synthesize a variety of penta-substituted pyrroles from α-nitroepoxides, primary amines and dialkyl acetylenedicarboxylates under the conditions without catalyst. Furthermore, the controlled experi
Gold catalyzed synthesis of tetrahydropyrimidines and octahydroquinazolines under ball milling conditions and evaluation of anticonvulsant potency
Vadivelu,Raheem,Sugirdha,Bhaskar,Karthikeyan,Praveen
supporting information, p. 90 - 101 (2018/02/07)
A fast, mechanochemical and solvent-free synthesis of substituted tetrahydropyrimidines and octahydroquinazolines under Au(III)-catalysis has been developed. The practical feasibility, eco-friendliness and operational simplicity of this chemistry is exemplified by ball milling three components such as formaldehyde, amines and 2-butynedioates/dimedone in a shaker mill for as little as five minutes, thus avoiding the requirement of undesirable solvents and long reaction times. Moreover, this protocol furnishes the target compounds in high yields without any side products and in some cases offers products with excellent regioselectivity. Out of the 26 compounds screened for anticonvulsant potency, 11 compounds exhibited comparable activity against a standard drug.
