- Efficient synthesis of decahydroacridine-1,8-diones and polyhydroquinolines using the step-wise method
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Various symmetrical and unsymmetrical decahydroacridine-1,8-dione and polyhydroquinoline derivatives were synthesized via two-step cyclocondensation reactions. The advantages of this step-wise addition of reactants in comparison with other one-pot reactions are avoiding the formation of 2 or 3 undesired by-products, therefore allowing cleaner work up of reaction. The important factor of this effective cyclocondensation method is that the prepared β-enaminone component was added dropwise to the solution, in which the Knoevenagel condensation product is slowly being formed by reaction of aldehyde molecule and 1,3-dicarbonyl compounds. The results of the proposed step-wise method are compared and discussed with those obtained in the one-pot reactions.
- Hosseininasab, Fatemeh Sadat,Memarian, Hamid Reza
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- On the enantioselective phosphoric-acid-catalyzed hantzsch synthesis of polyhydroquinolines
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A reinvestigation of a chiral phosphoric-acid-catalyzed four-component Hantzsch enantioselective synthesis of polyhydroquinolines reported in 2009 is presented. In our hands, when the reaction was performed with fidelity to the original report using a chiral enantiopure phosphoric acid catalyst, no enantioselectivity was observed. Unlike in the original report, enantioselectivity results are backed by baseline separation of the enantiomers by HPLC analyses on chiral stationary phase with UV and chiroptical detection.
- Bonne, Damien,Bressy, Cyril,Bugaut, Xavier,Constantieux, Thierry,Jean, Marion,Lemaitre, Clément,Quinonero, Ophélie,Rodriguez, Jean,Roussel, Christian,Vanthuyne, Nicolas
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supporting information
p. 3394 - 3398
(2021/05/29)
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- SHP2 INHIBITORS, COMPOSITIONS AND USES THEREOF
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Provided are compounds of Formula (I), methods of using the compounds as SHP2 inhibitors, and pharmaceutical compositions comprising such compounds. The compounds are useful in treating SHP2-mediated diseases.
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Page/Page column 110
(2021/12/30)
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- Copper-Catalyzed Thiolation of Terminal Alkynes Employing Thiocyanate as the Sulfur Source Leading to Enaminone-Based Alkynyl Sulfides under Ambient Conditions
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A highly efficient protocol for copper-catalyzed thio-alkynylation of enaminone-based thiocyanates with terminal alkynes under mild conditions has been developed. This scalable amino group-directed thio-alkynylation proceeds in the open air with a broad substrate scope and an excellent yield. The demonstrated synthetic transformation creates the opportunity for a wide variety of sulfur-containing useful materials. Gram-scale synthesis and further synthetic transformations of alkynyl sulfides highlight the potential utility of the method.
- Chandran,Pise, Ashwini,Shah, Suraj Kumar,Rahul,Suman,Tiwari, Keshri Nath
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supporting information
p. 6557 - 6561
(2020/08/24)
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- Cu catalyzed cross-dehydrogenative coupling reaction for the synthesis of 3-hydroxy-2-pyrrolidinones
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A new convenient strategy for the synthesis of 3-hydroxy-2-pyrrolidinone derivatives featuring regioselective C–C coupling has been developed. This is a Cu (II) catalyzed cross dehydrogenative coupling (CDC) involving enamino-ketones of benzyl amines and di-alkyl acetylenedicarboxylate, followed by cyclization by primary amines. TBHP (tert-butyl hydroperoxide) has been used as the oxidant to promote the coupling protocol. This synthetic route principally demonstrates the scope of CDC reaction and also applicable to gram-scale synthesis.
- Sarkar, Rajib,Mukhopadhyay, Chhanda
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p. 3069 - 3076
(2018/07/06)
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- 6 Hz active anticonvulsant fluorinated n-benzamide enaminones and their inhibitory neuronal activity
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A small library of novel fluorinated N-benzamide enaminones were synthesized and evaluated in a battery of acute preclinical seizure models. Three compounds (GSA 62, TTA 35, and WWB 67) were found to have good anticonvulsant activity in the 6-Hz ‘psychomotor’ 44-mA rodent model. The focus of this study was to elucidate the active analogs’ mode of action on seizure-related molecular targets. Electrophysiology studies were employed to evaluate the compounds’ ability to inhibit neuronal activity in central olfactory neurons, mitral cells, and sensory-like ND7/23 cells, which express an assortment of voltage and ligand-gated ion channels. We did not find any significant effects of the three compounds on action potential generation in mitral cells. The treatment of ND7/23 cells with 50 μM of GSA 62, TTA 35, and WWB 67 generated a significant reduction in the amplitude of whole-cell sodium currents. Similar treatment of ND7/23 cells with these compounds had no effect on T-type calcium currents, indicating that fluorinated N-benzamide enaminone analogs may have a selective effect on voltage-gated sodium channels, but not calcium channels.
- Amaye, Isis J.,Heinbockel, Thomas,Woods, Julia,Wang, Zejun,Martin-Caraballo, Miguel,Jackson-Ayotunde, Patrice
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- Efficient synthesis of acridinediones in aqueous media
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An efficient synthesis of acridinediones in two steps have been achieved using water as a reaction media without chromatographic purification. First step involves the reaction of dimedone with ammonium acetate to yield enaminone in water which on further
- Tiwari, Keshri Nath,Uttam, Mane Rajendra,Kumari, Puja,Vatsa, Piyush,Prabhakaran
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p. 1013 - 1019
(2017/05/04)
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- Synthesis and biological activity of 2′, 3′-iso-aryl-abscisic acid analogs
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2′, 3′-iso-Benzoabscisic acid (iso-PhABA), an excellent selective abscisic acid (ABA) analog, was developed in our previous work. In order to find its more structure-activity information, some structural modifications were completed in this paper, includi
- Wan, Chuan,Wang, Mingan,Yang, Dongyan,Han, Xiaoqiang,Che, Chuanliang,Ding, Shanshan,Xiao, Yumei,Qin, Zhaohai
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- Ammonium acetate as a catalyst and/or reactant in the reaction of dimedone, aromatic aldehyde, and malononitrile: synthesis of tetrahydrobenzo[b]pyrans and hexahydroquinolines
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Abstract: The reaction of aromatic aldehydes, dimedone, and malononitrile in the presence of ammonium acetate has afforded tetrahydrobenzo[b]pyrans instead of polyhydroquinolines under both grinding and reflux conditions; thus ammonium acetate acts as a c
- Moshtaghi Zonouz, Adeleh,Okhravi, Somaieh,Moghani, Davood
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p. 1819 - 1824
(2016/09/28)
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- Evaluation of magnetically recyclable nano-Fe3O4 as a green catalyst for the synthesis of mono- and bis-tetrahydro-4H-chromene and mono and bis 1,4-dihydropyridine derivatives
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Magnetically separable Fe3O4 nanoparticles were used as an environmental friendly catalyst for the synthesis of mono- and bis-tetrahydro-4H-chromene and mono- and bis-1,4-dihydropyridine derivatives via three-component reactions of aromatic aldehydes and malononitrile with cyclic β-dicarbonyls or cyclic β-enaminoketones respectively. These reactions were carried out in EtOH and at reflux. Fe3O4 nanoparticles can be magnetically separated from the reaction mixture by a magnet and recycled without significant loss of catalytic activity.
- Amirheidari, Bagher,Seifi, Mohammad,Abaszadeh, Mehdi
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p. 3413 - 3423
(2016/03/30)
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- Ionic liquid supported nanoporous silica (SBA-IL) as an efficient and heterogeneous catalyst in the domino synthesis of polyhydroquinoline derivatives
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A simple, efficient, and environmentally benign protocol for the synthesis of polyhydroquinoline derivatives was developed using a bio-compatible, heterogeneous, and recoverable mesoporous ionic liquid supported nanoporous silica as a nano-catalyst. The p
- Mohammadi Ziarani, Ghodsi,Seyedakbari, Leila,Asadi, Shima,Badiei, Alireza,Yadavi, Marzieeh
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p. 499 - 509
(2016/04/26)
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- FeCl3-Catalyzed Combinatorial Synthesis of Functionalized Spiro[Indolo-3,10′-indeno [1,2- b ]quinolin]-trione Derivatives
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An efficient, inexpensive, environmentally friendly and high yield one-pot route to new spiro[indolo-3,10′-indeno [1,2-b]quinolin]-trione derivatives has been developed, involving three-component reaction of enaminones, N-substituted isatins and Indane-1,3-dione catalyzed by FeCl3. The approach to this spiro-heterocycle is noteworthy because it results in the formation of three new σ (two C-C and one C-N) bonds in a single operation, leading to the construction of novel spiro skeleton. This method works on a large scale in excellent yields.
- Mondal, Animesh,Mukhopadhyay, Chhanda
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supporting information
p. 404 - 408
(2016/01/15)
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- COMPLEMENT PATHWAY MODULATORS AND USES THEREOF
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The present invention provides a compound of formula I: a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.
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Page/Page column 75
(2014/01/17)
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- Synthesis of chiral cyclic β-amino ketones by Ru-catalyzed asymmetric hydrogenation
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Synthesis of chiral cyclic β-amino ketones has been first reported via Ru-catalyzed asymmetric hydrogenation. High enantioselectivities were achieved by using (S)-C3-TunePhos chiral ligand (up to 94% ee).
- Huang, Kexuan,Guan, Zheng-Hui,Zhang, Xumu
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supporting information
p. 1686 - 1688
(2014/03/21)
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- Synthesis and antiproliferative activity evaluation of imidazole-based indeno[1,2-b]quinoline-9,11-dione derivatives
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A series of new imidazole substituted indeno[1,2-b]quinoline-9,11-dione derivatives were synthesized and evaluated for their antiproliferative effects on HeLa, LS180, MCF-7 and Jurkat human cancer cell lines. Antiproliferative effects were evaluated using MTT assay. Prepared compounds exhibited weak to good antiproliferative activity in evaluated cell lines. Prepared compounds were more potent in Jurkat cell line when compared to LS180, HeLa and MCF-7 cell lines. Compounds 29 (IC16 = 0.7 μM) and 31 (IC16 = 1.7 μM) and 33 (IC16 = 1.7 μM) were found to be the most potent molecules on Jurkat cell lines. Moreover; it was found that some of the tested compounds bearing imidazole-2-yl moiety on the C11-position of dihydropyridine ring exhibited superior antiproliferative activity in comparison to cis-platin especially in Jurkat cell line (compounds 29, 31, and 33). It seemed that the introduction of electron-withdrawing groups on the imidazole ring enhanced the antiproliferative potential of these compounds (compounds 27, 29 and 31). The results of this study proposed that some of the imidazole substituted indeno[1,2-b]quinoline-9,11-dione compounds may act as efficient anticancer agents in vitro, emphasizing their potential role as a source for rational design of potent antiproliferative agents.
- Sarkarzadeh, Hasti,Miri, Ramin,Firuzi, Omidreza,Amini, Mohsen,Razzaghi-Asl, Nima,Edraki, Najmeh,Shafiee, Abbas
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p. 436 - 447
(2013/07/28)
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- CRYSTALLINE FORMS OF OCTAHYDRO-3H-SPIRO [FURO [3, 4-C] QUINOLINE -1, 4 '-PYRAN] -9-OL
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The present invention relates to crystalline forms of the compound of formula (I) as shown in the description and its hydrochloride or hydrobromide salts, to a process for the manufacture thereof, and to the use thereof in pharmaceutical compositions.
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Page/Page column 44
(2013/03/26)
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- Crystalline forms of a hexahydrofuro[3,4-c]quinoline derivative
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The present invention relates to crystalline forms of (3R,9S)-4-isopropyl-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2′,3′,5′,6,6′,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4′-pyran]-9-ol and its hydrochloride or hydrobromide salts, to a process for the manufacture thereof, and to the use thereof in pharmaceutical compositions.
- -
-
Paragraph 0221-0226
(2013/08/28)
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- A new MCM-41 supported HPF6 catalyst for the library synthesis of highly substituted 1,4-dihydropyridines and oxidation to pyridines: Report of one-dimensional packing towards LMSOMs and studies on their photophysical properties
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A new heterogeneous MCM-41 silica supported HPF6 catalyst has been synthesized and characterized using an array of sophisticated analytical techniques like BET, XRD, HRTEM, EDX, 29Si MAS NMR, TGA, FTIR, and pH measurement. The broad
- Ray, Suman,Brown, Mike,Bhaumik, Asim,Dutta, Arghya,Mukhopadhyay, Chhanda
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p. 1910 - 1924
(2013/09/24)
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- Palladium-catalyzed oxidative annulation via C-H/N-H functionalization: Access to substituted pyrroles
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Pyrroles, ubiquitous bioactive heterocycles in nature, are readily prepared via a palladium-catalyzed oxidative annulation of cyclic trans-enamines to various internal alkynes in the absence of a directing group. Copyright
- Peng, Shiyong,Wang, Lei,Huang, Jiayao,Sun, Shaofa,Guo, Haibing,Wang, Jian
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supporting information
p. 2550 - 2557
(2013/10/21)
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- METABOTROPIC GLUTAMATE RECEPTOR MODULATORS
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The invention relates to heterocyclic derivatives of formula (I) as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are mGluR5 modulators and are therefore useful for the control and prevention of acute and/or chronic neurological disorders wherein Y, W, R1, R2 and R3 are as defined in claim 1.
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Page/Page column 47
(2012/05/05)
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- Enaminones 12. An explanation of anticonvulsant activity and toxicity per Linus Pauling's clathrate hypothesis
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The x-ray crystal structure of 3-((5-methylisoxazol-3-yl)amino)-5- methylcyclohex-2-enone (12b) and 3-((5-methylisoxazolyl-3-yl)amino)-5,5- dimethylcyclohex-2-enone (12c) were determined and correlated to their anticonvulsant activity in mice and rats. A hypothesis for the toxicity of the analogs are advanced. In addition, a series of 5-methyl-N-(3-oxocyclohex-1-enyl) -isoxazole-3-carboxamides were synthesized and evaluated for anticonvulsant activity. These compounds were compared to the activity of the corresponding amino and aminomethyl enaminones. Additional investigation involved the synthesis and evaluation of a trifluoromethyl analog of the active isoxazole tert-butyl 4-(5-methisoxazol-3-yl-amino)-6-methyl-2-oxo-cyclohex-3-ene carboxylate (4f).
- Jackson, Patrice L.,Hanson, Clive D.,Farrell, Alanna K.,Butcher, Raymond J.,Stables, James P.,Eddington, Natalie D.,Scott
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experimental part
p. 42 - 51
(2012/07/28)
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- Solid-state synthesis of β-enamino ketones from solid 1,3-dicarbonyl compounds and ammonium salts or amines
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A facile amination of solid 1,3-dicarbonyl compounds with ammonium salts or amines in solid state has been achieved by mechanochemical grinding in the presence of KHSO4 and SiO2. Most of the reactions proceed smoothly at room temperature under solid-state conditions and give their corresponding β-imino derivatives in high yields. The method has the advantage of simple manipulation and mild conditions. Georg Thieme Verlag Stuttgart.
- Xu, Shi-Liang,Li, Cheng-Ping,Li, Jing-Hua
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experimental part
p. 818 - 822
(2009/07/18)
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- Partially saturated indeno[1,2-b]indole derivatives via deoxygenation of heterocyclic α-hydroxy-N,O-hemiaminals
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A series of 3-aminocyclohex-2-enones were reacted with indane-1,2,3-trione monohydrate (ninhydrin) yielding 4b,9b-dihydroxyindeno[ 1,2-b]indoles that were deoxygenated to indeno[1,2-b]indoles. Georg Thieme Verlag Stuttgart.
- Hemmerling, Hans-Joerg,Reiss, Guido
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experimental part
p. 985 - 999
(2009/12/01)
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- TETRAHYDROQUINOLINONES AND THEIR USE AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS
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The invention relates to ethynyl-substituted tetrahydroquinolinone derivatives as well as their pharmaceutically acceptable a salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are group
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Page/Page column 27
(2008/06/13)
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- TETRAHYDROQUINOLINONES AND THEIR USE AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS
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The invention relates to ethynyl-substituted tetrahydroquinolinone derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are group I
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Page/Page column 27
(2008/06/13)
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- Efficient synthesis of β-amino-α,β-unsaturated carbonyl compounds
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A versatile and high-yielding procedure for the synthesis of β-enamino esters and β-enaminones is presented: in the presence of tetraethyl orthosilicate, a number of highly functional β-enamino esters were obtained; this method provided an alternative for the formation of β-amino-α,β-unsaturated carbonyl compounds with mild and functional group compatible reaction conditions. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2005.
- Zhao, Yuanhong,Zhao, Jingfeng,Zhou, Yongyun,Lei, Ze,Li, Liang,Zhang, Hongbin
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p. 769 - 772
(2007/10/03)
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- Enaminones as building blocks in heterocyclic syntheses: A new approach to polyfunctionally substituted cyclohexenoazines
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A variety of polyfunctionally substituted condensed pyridines and pyrazolotetrahydroquinazolines have been synthesized utilizing cyclic enaminones as starting materials.
- Al-Mousawi, Saleh,Abdelkhalik, Mervat Mohammed,John, Elizabeth,Elnagdi, Mohammed Hilmy
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p. 689 - 695
(2007/10/03)
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- Efficient synthesis of quinazolinones as intermediates of CNS agents via inverse-electron demand Diels-Alder reaction
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Enaminones undergo inverse electron demand Diels-Alder reaction with 1,3,5-triazine, allowing access to functionalised quinazolinones as intermediates in the synthesis of CNS agents. This reaction is highly dependent of the solvent: 1,3,5-triazine undergo
- Bilbao, Estibaliz R.,Alvarado, Mario,Masaguer, Christian F.,Ravi?a, Enrique
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p. 3551 - 3554
(2007/10/03)
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- Synthesis, 1H, 13C and 15N NMR study of Azo coupling products from enaminones
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Compounds 2 were prepared by the reaction of 3-amino-5,5- dimethylcyclohex-2-en-1-one and its N-phenyl derivative with substituted benzenediazonium tetrafluoroborates, and their 1H, 13C and 15N NMR spectra were measured and analysed. The active components react with enaminones in molar ratios of 2:1. Only in the case of 4-methoxybenzenediazonium tetrafluoroborate and 3-amino-5,5-dimethylcyclohex-2-en-1-one were traces of the product of the 1:1 reaction observed. The attack by the diazonium component occurs at carbon atoms C-2 and C-4, and the hydrazo form is always formed at the 2-position. 15N NMR spectroscopy was adopted to study the position of the tautomeric equilibrium (arylazo -arylhydrazono) at the 4-position: This equilibrium depends predominantly on the substituents of the amino group and, to a lesser extent, on the substituents of the diazonium component. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
- Simunek, Petr,Lycka, Antonin,Machacek, Vladimir
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p. 2764 - 2769
(2007/10/03)
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- Synthesis, characterization and anticonvulsant activity of enaminones. Part 6: Synthesis of substituted vinylic benzamides as potential anticonvulsants
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A comparison of enaminones from various unsubstituted and p-substituted benzamides to the analogous benzylamines has been undertaken with the aim of elucidating the essential structural parameters necessary for anticonvulsant activity. Initial studies on methyl 4-N-(benzylamino)-6-methyl-2-oxocyclohex- 3-en-1-oate, 3a, 3-N-(benzylamino)cyclohex-2-en-1-one, 3p, and 5,5-dimethyl- 3-N-(benzylamino)-cyclohex-2-en-1-one, 3r indicated that benzylamines possessed significant anti-maximal electroshock seizure (MES) activity. Evaluation of the analogous benzamides revealed significant differences in anticonvulsant activity, these differences were most probably related to the differences in their three-dimensional structures. (C) 1999 Elsevier Science Ltd.
- Foster, James E.,Nicholson, Jesse M.,Butcher, Raymond,Stables, James P.,Edafiogho, Ivan O.,Goodwin, Angela M.,Henson, Michael C.,Smith, Carlynn A.,Scott
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p. 2415 - 2425
(2007/10/03)
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- The mechanism of the reaction of the Nash and the Sawicki aldehyde reagent
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Synthetic and chromatographic studies are presented on the Nash and Sawicki colorimetric methods for quantitating formaldehyde.It is shown that the actual color-forming agent in the Nash method is an isolable iminodione formed in situ by reaciton of the t
- Compton, Bruce Jon,Purdy, William C.
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p. 2207 - 2211
(2007/10/02)
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