- De Novo Construction of Substituted Terephthalates via Phosphine Catalyzed Domino Benzannulation Reactions
-
The robustness of phosphine catalysis enabling the domino benzannulation reactions of allenoates with enamines is described. A broad array of substituted terephthalates were delivered under simple and practical reaction conditions. Furthermore, the reaction could be carried out on a gram scale with higher yield, and various conversions of the terephthalate products demonstrate the versatility of this transformation. (Figure presented.).
- Wang, Dan,Lin, Junhui,Zhu, Yannan,Huang, You
-
supporting information
p. 1873 - 1877
(2021/02/16)
-
- Consecutive Three-Component Coupling-Addition Synthesis of β-Amino Enoates and 3-Hydroxypyrazoles via Ethyl 3-Arylpropiolates
-
Two consecutive three-component syntheses furnishing β-amino enoates or 3-hydroxypyrazoles based upon the Sonogashira alkynylation of aryl iodides and ethyl propiolate were established in mostly excellent yields. The ethyl 3-arylpropiolate intermediates are Michael systems which are suited for concatenation with conjugate addition or cyclocondensation giving access to libraries of 21 different β-amino enoates and 17 different 3-hydroxypyrazoles. The rotational barrier of β-pyrrolidino enoates was assessed by studying the coalescence of pyrrolidinyl protons in VT-NMR spectra of electronically different substituted derivatives showing that the electronic substituent effect on the aryl group does not affect the height of the rotational barrier. This indicates that the substituents are essentially oriented orthogonally to the plane of the β-pyrrolidino enoates.
- Niedballa, Jonas,Reiss, Guido J.,Müller, Thomas J. J.
-
supporting information
p. 5019 - 5024
(2020/07/24)
-
- 3-Phenothiazinyl propiolates – Fluorescent electrophores by Sonogashira coupling of ethyl propiolate
-
Fluorescent ethyl 3-phenothiazinyl propiolates with reversible Nernstian oxidation potentials were efficiently synthesized by an improved Sonogashira coupling of aryl iodides and ethyl propiolate. The versatility of this modified alkynylation was illustrated by 13 ethyl 3-arylpropiolates in mostly excellent yields with a broad substrate scope. In addition to reversible one-electron oxidations, the title compounds reveal large Stokes shifts, high fluorescence quantum yields, and solvatochromic emission. The photophysical characteristics were corroborated and rationalized by DFT and TD-DFT calculations.
- G?tzinger, Alissa C.,Michaelis, Carina S.,Müller, Thomas J.J.
-
p. 308 - 316
(2017/05/04)
-
- Gold-catalyzed Fluorination of Alkynyl Esters and Ketones: Efficient Access to Fluorinated 1,3-Dicarbonyl Compounds
-
We developed an efficient synthesis of 2-fluoro-1,3-dicarbonyl compounds using readily available alkynyl ketones or esters as starting material. The key step is the insertion of hydrogen fluoride (HF) to the gold carbene intermediate generated from cationic gold catalyzed addition of N-oxides to alkynyl ketones or esters. This method gives excellent chemical yields and regioselectivity with good functional group tolerance. (Figure presented.).
- Zeng, Xiaojun,Lu, Zhichao,Liu, Shiwen,Hammond, Gerald B.,Xu, Bo
-
supporting information
p. 4062 - 4066
(2017/11/30)
-
- Copper(i)/phosphine-catalyzed tandem carboxylation/annulation of terminal alkynes under ambient pressure of CO2: One-pot access to 3a-hydroxyisoxazolo[3,2-a]isoindol-8(3aH)-ones
-
An efficient method for the synthesis of 3a-hydroxyisoxazolo[3,2-a]isoindol-8(3aH)-ones from CO2, terminal alkynes, EtBr, and NHPI (N-hydroxyphthalimide) was developed through a tandem carboxylation/annulation strategy catalyzed by a copper(i)/phosphine system. This one-pot multicomponent reaction was conducted at atmospheric CO2 pressure to afford the target products in good to excellent yields under mild conditions. Notably, a wide range of functional groups were tolerated in this procedure. This protocol with simultaneous formation of four novel bonds i.e. two C-C bonds and two C-O bonds represents an efficient methodology for upgrading CO2 into heterocycles.
- Xie, Jia-Ning,Yu, Bing,Guo, Chun-Xiang,He, Liang-Nian
-
p. 4061 - 4067
(2015/07/15)
-
- Structural design and synthesis of arylalkynyl amide-type peroxisome proliferator-activated receptor γ3 (PPAR γ3)-selective antagonists based on the helix12-folding inhibition hypothesis
-
Peroxisome proliferator-activated receptor γ3 (PPARγ3) antagonists are candidates for treatment of type 2 diabetes, obesity and osteoporosis. However, few rational design strategies are currently available. Here, we utilized the helix12 (H12)-folding inhi
- Ohashi, Masao,Gamo, Kanae,Tanaka, Yuta,Waki, Minoru,Beniyama, Yoko,Matsuno, Kenji,Wada, Jun,Tenta, Masafumi,Eguchi, Jun,Makishima, Makoto,Matsuura, Nobuyasu,Oyama, Takuji,Miyachi, Hiroyuki
-
-
- Ruthenium-catalyzed asymmetric [2 + 2] cycloadditions between chiral acyl camphorsultam-substituted alkynes and bicyclic alkenes
-
Ruthenium-catalyzed asymmetric [2 + 2] cycloadditions between chiral acyl camphorsultam-functionalized alkynes and bicyclic alkenes were examined, providing adducts with complete exo stereoselectivity in good overall yield and enantioselectivity (up to 99% and 166:1, respectively), as well as appreciable diastereoselectivity (up to 163:1). The diastereoselectivity showed dependence on the solvent and temperature, as well as on the substitution pattern of the reacting alkyne and bicyclic alkene components. In general, higher diastereoselectivities were observed for reactions conducted in ethereal solvents and at lower temperatures between N-propynoyl camphorsultams and bicyclic alkenes.
- Goodreid, Jordan,Villeneuve, Karine,Carlson, Emily,Tam, William
-
p. 10002 - 10012
(2015/02/19)
-
- Ruthenium-catalyzed [2+2] cycloaddition reactions of a 2-oxa-3- azabicyclo[2.2.1]hept-5-ene with unsymmetrical alkynes
-
Ruthenium-catalyzed [2+2] cycloaddition reactions of a 2-oxa-3- azabicyclo[2.2.1]hept-5-ene with unsymmetrical alkynes were investigated. Yields of up to 90% were obtained though regioselectivity was modest. Select cycloadducts could be separated and used to access a highly functionalized [3.2.0] bicyclic structure through reductive cleavage of the N-O bond. These ring-opened products displayed a chemical exchange phenomenon in 1D carbon NMR and required characterization by 2D NMR techniques.
- Durham, Robin,Mandel, Jeremie,Blanchard, Nicolas,Tam, William
-
scheme or table
p. 1494 - 1505
(2012/01/12)
-
- Substituted indoles and their use as integrin antagonists
-
The present invention relates to novel substituted indole compounds that are antagonists of alpha V (αv) integrins, for example αvβ3 and αvβ5 integrins, their pharmaceutically acceptable salts, and pharmaceutical compositions thereof. The compounds may be used in the treatment of pathological conditions mediated by αvβ3 and αvβ5 integrins, including such conditions as tumor growth, metastasis, restenosis, osteoporosis, inflammation, macular degeneration, diabetic retinopathy, and rheumatoid arthritis. The compounds have the general formula: where R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, D, X, W, a, m, n, i, j, k and v are defined herein.
- -
-
-
- Synthesis and Biological Evaluation of a Series of Substituted 4,5-Diphenylpyridine-2,6(1H,5H)-diones
-
We report the synthesis of a series of disubstituted 4,5-diphenylpyridine-2,6(1H,5H)-diones (8), (10), (12)-(21), their characterization by 1H and 13 C n.m.r. spectroscopy and their receptor binding affinities for catecholamine and benzodiazepine receptors.
- Andrews, Peter R.,Brinkworth, Ross I.,Partridge, Ashton C.,Reiss, James A.
-
p. 1717 - 1726
(2007/10/02)
-
