- New Route to Functionalized Cyclohexenes in Solvent-free Conditions from Enamino Ketones and β-Oxo Alkenes
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Enamino ketones 5 react with β-oxo alkenes 4, without solvent, at room temperature or under focused microwaves to give new, highly functionalized cyclohexenes 7 and 9 in good yields. A mechanism is proposed. The procedure is mild, efficient, economical and environmentally benign. - Keywords: solvent-free reactions; enamino ketones; cyclohexenes; β-oxo alkenes
- Ayoubi, Sahar Abdallah-El,Toupet, Loic,Texier-Boullet, Francoise,Hamelin, Jack
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- Synthesis of Spiro-Δ2-Pyrrolin-4-One Pseudo Enantiomers via an Organocatalyzed Sulfa-Michael/Aldol Domino Sequence
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Δ2-Pyrrolin-4-ones undergo organocatalyzed sulfa-Michael/aldol domino spirocyclizations with mercaptoacetaldehyde dimer. The products contain three contiguous stereocenters (ee up to 99%, dr up to 95:5, 25 examples) and can be transformed into analogues of natural products. With the use of a single catalyst, the absolute configuration of the products were determined by the configuration of the exocyclic double bond of the starting material. These results point at the possibility of a widespread use of unsaturated Δ2-pyrrolin-4-ones in various (organo)catalyzed (cascade) transformations for accessing libraries of 3D-rich pyrrolone-based (spiro)heterocycles. (Figure presented.).
- Gro?elj, Uro?,Ciber, Luka,Gnidovec, Jan,Testen, ?an,Po?gan, Franc,?tefane, Bogdan,Tav?ar, Ga?per,Svete, Jurij,Ri?ko, Sebastijan
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- Design of a graphene oxide-SnO2 nanocomposite with superior catalytic efficiency for the synthesis of β-enaminones and β-enaminoesters
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A graphene oxide (GO)-SnO2-based nanocomposite was synthesized by decorating the graphene oxide surface with SnO2 nanoparticles via a solvothermal process. The nanocomposite was characterized using Fourier transform infrared spectra (FTIR), FT-Raman spectroscopy, X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), Field-emission Scanning electron microscopy (FE-SEM), Energy dispersive X-ray spectroscopy (EDS), Transmission electron microscopy (TEM) and N2 adsorption/desorption study. The FE-SEM and TEM images demonstrate the uniform distribution of the SnO2 nanoparticles on the GO surface and high-resolution transmission electron microscopy (HRTEM) confirms an average particle size of 8-12 nm. The GO-SnO2 nanocomposite has been found to be an extremely efficient catalyst for the synthesis of β-enaminones and β-enaminoesters in methanol solvent and also, in solventless conditions. The GO-SnO2 nanocomposites exhibited synergistically more superior catalytic efficiency compared to pure graphene oxide and SnO2 nanoparticles. The reaction conditions were optimized by changing different parameters such as catalyst, solvent, catalyst loading, and temperature. It has been found that the catalyst gave higher activity under solventless conditions than methanol. The GO-SnO2 composite was recycled for up to four cycles with minimal loss in activity.
- Kumar, Aniket,Rout, Lipeeka,Dhaka, Rajendra S.,Samal, Saroj L.,Dash, Priyabrat
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p. 39193 - 39204
(2015/05/20)
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- Bexarotene prodrugs: Targeting through cleavage by NQO1 (DT-diaphorase)
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Bexarotene, a retinoid X receptor (RXR) agonist, is being tested as a potential disease modifying treatment for neurodegenerative conditions. To limit the peripheral exposure of bexarotene and release it only in the affected areas of the brain, we designe
- Sch?fer, Anja,Burstein, Ethan S.,Olsson, Roger
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supporting information
p. 1944 - 1947
(2014/04/17)
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- Isoquinolin-1(2H)-ones and 1,6-naphthyridin-5(6H)-ones by an N-acylation-SNAr sequence
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A new synthesis of 2,3-dialkyl-4-carbomethoxyisoquinolin-1(2H)-ones and 6,7-dialkyl-8-carbomethoxy-1,6-naphthyridin-5(6H)-ones is reported. The process involves treatment of a β-enaminoester with 2-fluoro-5-nitrobenzoyl chloride, 2-fluorobenzoyl chloride or 2-chloronicotinoyl chloride followed by heating in the presence of base. The conversion, which proceeds by an N-acylation-SNAr reaction sequence, affords 50-86% yields when R 1 is n-alkyl but ≤30% yields when R1 is α-branched.
- Bunce, Richard A.,Nammalwar, Baskar,Gnanasekaran, Krishna Kumar,Cain, Nicholas R.
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p. 838 - 844
(2014/01/23)
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- LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS
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Compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or diagnose diseases, disorders, or conditions associated with one or more of the lysophosphatidic acid receptors are provided.
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Paragraph 0402
(2013/03/26)
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- FUNGICIDAL PYRAZOLES
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Disclosed are compounds of Formula (1) and Formula (1A) including all stereoisomers, N oxides, and salts thereof,wherein Q1, Q2, R1, R2, R4, R5 and X are as defined in the disclosure. Also
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Page/Page column 44
(2012/03/26)
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- POLYCYCLIC LPA1 ANTAGONIST AND USES THEREOF
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Described herein is the LPA1 antagonist 1- {4'-[3-methyl-4-((R)- l-phenyl-ethoxycarbonylamino)- isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid (Compound 1), or pharmaceutically acceptable salts thereof. Also described are methods of preparing t
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Page/Page column 87
(2012/06/30)
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- Cu(OAc)2/TFA-promoted formal [3 + 3] cycloaddition/oxidation of enamines and enones for synthesis of multisubstituted aromatic amines
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New strategies for the oxidative cycloaddition of enones with enamines are developed. These cycloaddition reactions directly afford substituted aromatic amines, which are important in organic chemistry, in moderate to good yield. Cu(OAc)2/TFA is shown to be essential to achieve high reaction efficiency.
- Li, Liang,Zhao, Mi-Na,Ren, Zhi-Hui,Li, Jian-Li,Guan, Zheng-Hui
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supporting information; experimental part
p. 3506 - 3509
(2012/08/08)
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- LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS
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Described herein are compounds that are antagonists of lysophosphatidic receptor(s). Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such antagonists, alone and in com
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Page/Page column 40
(2012/10/18)
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- POLYCYCLIC COMPOUNDS AS LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS
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Described herein are compounds that are antagonists of lysophosphatidic receptor(s). Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such antagonists, alone and in combination with other compounds, for treating LPA-dependent or LPA-mediated conditions or diseases.
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Page/Page column 23
(2011/04/24)
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- Compounds as Lysophosphatidic Acid Receptor Antagonists
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Described herein are compounds that are antagonists of lysophosphatidic receptor(s). Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such antagonists, alone and in com
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Page/Page column 15
(2011/04/24)
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- LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONIST AND USES THEREOF
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Described herein is the LPAl antagonist {4'-[3-methyl-4-((R)-l-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-biphenyl-4-yl}-acetic acid (Compound 1), including pharmaceutically acceptable salts thereof. Also described are methods of preparing the LPAl antago
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Page/Page column 78-79
(2012/01/06)
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- ALKYNE ANTAGONISTS OF LYSOPHOSPHATIDIC ACID RECEPTORS
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Described herein are compounds that are antagonists of lysophosphatidic receptor(s). Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such antagonists, alone and in com
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Page/Page column 50; 104
(2010/07/02)
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- ANTAGONISTS OF LYSOPHOSPHATIDIC ACID RECEPTORS
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Described herein are compounds that are antagonists of lysophosphatidic receptor(s). Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such antagonists, alone and in combination with other compounds, for treating LPA-dependent or LPA-mediated conditions or diseases.
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Page/Page column 17
(2010/06/22)
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- POLYCYCLIC ANTAGONISTS OF LYSOPHOSPHATIDIC ACID RECEPTORS
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Described herein are compounds that are antagonists of lysophosphatidic receptor(s). Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such antagonists, alone and in combination with other compounds, for treating LPA-dependent or LPA-mediated conditions or diseases.
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Page/Page column 41-42
(2010/12/29)
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- Synthesis of indolequinones from bromoquinones and enamines mediated by Cu(OAc)2H2O
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A Cu(II)-mediated synthesis of indolequinones from the corresponding bromoquinones and enamines is reported. The key oxidative cyclization proceeds in good yield for a broad range of substrates and can be performed on a multigram scale, allowing access to biologically interesting structures.
- Inman, Martyn,Moody, Christopher J.
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supporting information; experimental part
p. 6023 - 6026
(2010/11/20)
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- Novel isoxazole and thiazole compounds and use thereof as drugs
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The present invention relates to novel isoxazole and thiazole compounds having an excellent lysophosphatidic acid (LPA) receptor antagonistic activity represented by general formula [1] or salts thereof: wherein R1 and R2 represents an optionally substituted alkyl group or the like; R3 represents a hydrogen atom or the like; R4 represent a group selected from the group consisting of (I) optionally substituted phenyl, aryl, or heterocycle, (II) substituted or nonsubstituted alkyl, and (III) substituted or nonsubstituted alkenyl, alternatively, R3 and R4 may form a ring structure together with a carbon atom to which they bind; and X represents an oxygen atom or a sulfur atom, provided that, when R3 is a hydrogen atom, R4 represents a group other than methyl, and the use thereof as a medicine.
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- Addition du Methylazide aux Olefines Portant une Double Substitution Activante Geminee. Etude de la Stabilite Thermique des Triazol-1,2,3-inees Obtenues
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Methylazide reacts with alkenes bearing two electron-withdrawing substituents on the same sp2 carbone and leads to corresponding 1,2,3-triazolines with these substituents in 4 position.Thermolysis of these 1,2,3-triazolines give cycloreversion (alkene + methylazide) and aziridines after extrusion of nitrigen.In the conditions of the thermolysis, aziridine carbone-carbone bond breaks, leading to azomethine ylids that are trapped with alkenes and give pyrrolidines.
- Hetet, G. Le,Danion-Bougot, R.,Carrie, R.
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p. 259 - 272
(2007/10/03)
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- REACTION DU METHYLAZIDE AVEC DES OLEFINES CINNAMIQUES, CROTONIQUES ET ACRYLIQUES. ETUDE DES COMPOSES OBTENUS
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Methylazide reacts with the title olefines and gives expected 1,2,3-triazolines in equilibrium with corresponding amino dizao compounds.Because this equilibrium, E and Z olefines gives the same result, and the addition do not seem stereospecific.Thermolys
- Hetet, G. Le,Benhaoua, H.,Carrie, R.
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p. 189 - 204
(2007/10/03)
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- 1,4-Dihydropyridine esters
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A new class of 1,4-dihydropyridines which are characterized by the presence of ester substitutes at positions 3 and 5 of the nucleus and by the presence of an alkoxyalkyl at position 2. The products exhibit coronary activity and have particular application as coronary dilators, antifibrillators, anti-hypertensives, and as muscular and vascular spasmolytics.
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