6575-25-3Relevant academic research and scientific papers
Three-coordinate copper(II) alkynyl complex in C-C bond formation: The sesquicentennial of the glaser coupling
Warren, Timothy H.,Bakhoda, Abolghasem,Okoromoba, Otome E.,Greene, Christine,Boroujeni, Mahdi Raghibi,Bertke, Jeffery A.
supporting information, p. 18483 - 18490 (2020/11/27)
Copper(II) alkynyl species are proposed as key intermediates in numerous Cu-catalyzed C-C coupling reactions. Supported by a β-diketiminate ligand, the three-coordinate copper(II) alkynyl [CuII]-C≡CAr (Ar = 2,6-Cl2C6H3) forms upon reaction of the alkyne H-C≡CAr with the copper(II) tertbutoxide complex [CuII]-OtBu. In solution, this [CuII]-C≡CAr species cleanly transforms to the Glaser coupling product ArC≡C-C≡CAr and [CuI](solvent). Addition of nucleophiles R′C≡C-Li (R′ = aryl, silyl) and Ph-Li to [CuII]-C≡CAr affords the corresponding Csp-Csp and Csp-Csp2 coupled products RC≡C-C≡CAr and Ph-C≡CAr with concomitant generation of [CuI](solvent) and {[CuI]-C≡CAr}-, respectively. Supported by density functional theory (DFT) calculations, redox disproportionation forms [CuIII](C≡CAr)(R) species that reductively eliminate R-C≡CAr products. [CuII]-C≡CAr also captures the trityl radical Ph3C· to give Ph3C-C≡CAr. Radical capture represents the key Csp-Csp3 bond-forming step in the copper-catalyzed C-H functionalization of benzylic substrates R-H with alkynes H-C≡CR′ (R′ = (hetero)aryl, silyl) that provide Csp-Csp3 coupled products R-C≡CR via radical relay with tBuOOtBu as oxidant.
HORMONE RECEPTOR MODULATORS FOR TREATING METABOLIC MUTAGENIC AND FIBROTIC CONDITIONS AND DISORDERS
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, (2019/04/11)
The invention relates to activators of FXR useful in the treatment of autoimmune disorders, liver disease, intestinal disease, kidney disease, cancer, and other diseases in which FXR plays a role, having the Formula (I): wherein L1, A, X1
DBU-Mediated Synthesis of Aryl Acetylenes or 1-Bromoethynylarenes from Aldehydes
Thummala, Yadagiri,Karunakar, Galla V.,Doddi, Venkata Ramana
supporting information, p. 611 - 616 (2019/01/04)
Two well known synthetic organic reactions Ramirez olefination and Corey-fuchs reactions are integrated in one-pot sequential manner for the synthesis of arylacetylenes and 1,3-enynes starting directly from commercially available aldehydes. The bicyclic amidine 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) along with additive NaOH not only exclusively afforded the terminal alkynes directly from the aldehydes, but also enhanced the reaction rate. The dynamic nature of DBU also facilitated the isolation of 1-bromoalkynes intermediate products. Selection of additive from NaOH and H2O served as a switch for the synthesis of terminal alkyne and 1-bromoalkynes, respectively. (Figure presented.).
ARYL HYDROCARBON RECEPTOR (AHR) MODULATOR COMPOUNDS
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Page/Page column 28; 29, (2018/08/26)
The present invention relates to compounds which can act as aryl hydrocarbon receptor (AhR) modulators and, in particular, as AhR antagonists. The invention further relates to the use of the compounds for the treatment and/or prophylaxis of diseases and/or conditions through binding of said aryl hydrocarbon receptor by said compounds.
The Dual Role of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the Synthesis of Terminal Aryl- and Styryl-Acetylenes via Umpolung Reactivity
Morri, Ashok Kumar,Thummala, Yadagiri,Doddi, Venkata Ramana
, p. 4640 - 4643 (2015/09/28)
The dual role of the bicyclic amidine base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was demonstrated in a synthesis of terminal aryl- and styryl-acetylenes. Mechanistically, a tandem process involving elimination/Umpolung/protonation occurs in a single step to generate terminal aryl- and styryl-acetylenes from geminal dibromoalkenes. The key to the success of this transformation lies in the organobase-mediated generation of the acetylide from the 1-bromoalkynes at room temperature. The unique characteristics of DBU as an inherently safer reagent make it an attractive alternative to previous systems wherein required pyrophoric reagents and nonambient temperatures remain unsolved issues. The procedure does not work for the synthesis of alkyl-acetylenes.
INDOLE DERIVATIVES AS CRAC MODULATORS
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, (2012/01/30)
Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein R1, R2, R3 and R4 are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of diseases associated with calcium release-activated calcium channels (CRAC).
NOVEL FXR (NR1H4 ) BINDING AND ACTIVITY MODULATING COMPOUNDS
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, (2011/04/13)
The present invention relates to compounds which bind to the NR1 H4 receptor (FXR) and act as agonists of the NR1 H4 receptor (FXR). The invention further relates to the use of the compounds for the preparation of a medicament for the treatment of diseases and/or conditions through binding of said nuclear receptor by said compounds, and to a process for the synthesis of said compounds.
Regioselective hydrostannation of highly hindered arylalkynes under ortho-directing effects
Hamze, Abdallah,Le Menez, Patrick,Provot, Olivier,Morvan, Estelle,Brion, Jean-Daniel,Alami, Mouad
experimental part, p. 8698 - 8706 (2010/11/18)
Palladium-catalyzed hydrostannation reactions of ortho-disubstituted arylalkynes were achieved with total stereo- and regio-selectivity in THF at room temperature. The regioselectivity was found to be under the control of the ortho-substituents (ortho-dir
PYRROLO[2,3-d]PYRIMIDIN-2-YL-AMINE DERIVATIVES AS PKC-THETA INHIBITORS
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, (2009/11/29)
The present invention relates to a pyrrolo[2,3-d]pyrimidin-2-yl-amine derivative according to formula (I) wherein the variables are defined as in the specification, or to a pharmaceutically acceptable salt or solvate thereof. The present invention also re
Novel 3-phenylprop-2-ynylamines as inhibitors of mammalian squalene epoxidase.
Musso, David L,Clarke, Morris J,Kelley, James L,Boswell, G Evan,Chen, Grace
, p. 498 - 506 (2007/10/03)
The synthesis of a novel series of 3-phenylprop-2-ynylamines as selective mammalian squalene epoxidase inhibitors is described. Structure activity relationship studies led to the discovery of compound 19, 1-[3-(3,5-dichlorophenyl)-prop-2-ynyl]-3- methylpiperidine hydrochloride with an IC50 of 2.8 +/- 0.6 microM against rat liver squalene epoxidase. Against 23 strains of fungal squalene epoxidase compound 19 was found to be inactive.
