143564-88-9Relevant academic research and scientific papers
Enantioselective Synthesis of γ-Functionalized Cyclopentenones and δ-Functionalized Cycloheptenones Utilizing a Redox-Relay Heck Strategy
Yuan, Qianjia,Prater, Matthew B.,Sigman, Matthew S.
, p. 326 - 330 (2020)
In this report, the desymmetrization of cyclic enones under relay Heck conditions with an array of aryl boronic acids, alkenyl triflates and indole derivatives is described. This method grants facile access to diverse γ-functionalized cyclopentenones and δ-functionalized cycloheptenones. Using this approach, a formal synthesis of (S)-baclofen was completed in high yield and excellent enantioselectivity. (Figure presented.).
Pd-Catalyzed Difluoromethylation of Vinyl Bromides, Triflates, Tosylates, and Nonaflates
Chang, Dalu,Gu, Yang,Shen, Qilong
supporting information, p. 6074 - 6078 (2015/04/14)
Pd-catalyzed difluoromethylation of di-, tri- or tetra-substituted vinyl bromides, triflates, tosylates and nonaflates under mild conditions is described. The reaction tolerates a wide range of functional groups, such as bromide, chloride, fluoride, ester, amine, nitrile, and protected carbonyl, thus providing a general route for the preparation of difluoromethylated alkenes. Vinyl fantasy: Pd-catalyzed difluoromethylation of di-, tri-, or tetra-substituted vinyl bromides, triflates, tosylates, and nonaflates under mild conditions is described. The reaction tolerates a wide range of functional groups, such as bromide, chloride, fluoride, ester, amine, nitrile, and protected carbonyl, thus providing a general route for the preparation of difluoromethylated alkenes.
Synthesis of substituted pyrazoles via tandem cross-coupling/ electrocyclization of enol triflates and diazoacetates
Babinski, David J.,Aguilar, Hector R.,Still, Raymond,Frantz, Doug E.
experimental part, p. 5915 - 5923 (2011/10/02)
The synthesis of 3,4,5-trisubstituted pyrazoles via a tandem catalytic cross-coupling/electrocyclization of enol triflates and diazoacetates is presented. The initial scope of this methodology is demonstrated on a range of differentially substituted acyclic and cyclic enol triflates as well as an elaborated set of diazoacetates to provide the corresponding pyrazoles with a high degree of structural complexity.
Stereoselective synthesis of acetoacetate-derived enol triflates
Babinski, David,Soltani, Omid,Frantz, Doug E.
supporting information; experimental part, p. 2901 - 2904 (2009/05/30)
(Chemical Equation Presented) A highly stereoselective method for preparing (Z)- and (E)-enol triflates derived from substituted acetoacetate derivatives is described. The salient feature of this methodology is the use of Schotten-Baumann-type conditions
Convenient synthesis of electron deficient dienes via Pd(0) catalyzed coupling
Kim, Hwa-Ok,Ogbu, Cyprian O.,Nelson, Sherry,Kahn, Michael
, p. 1059 - 1060 (2007/10/03)
The convenient preparation of 1,6-dicarbonyl-2,4-butadienes by the coupling of enol triflates with α,β-unsaturated carbonyls in the presence of Pd(PPh2)2Cl2 is described.
Imidazole-5-acrylic Acids: Potent Nonpeptide Angiotensin II Receptor Antagonists Designed Using a Novel Peptide Pharmacophore Model
Keenan, R.M.,Weinstock, J.,Finkelstein, J.A.,Franz, R.G.,Gaitanopoulos, D.E.,et al.
, p. 3858 - 3872 (2007/10/02)
A series a novel nonpeptide angiotensin II receptor antagonists containing a substituted (E)-acrylic acid has been developed.The overlay of 1, an imidazole-5-acetic acid found in the patent literature, on a novel pharmacophore model of AII suggested that extension of the acid side chain and attachment of a second aryl residue to mimic the C-terminal phenylalanine region of AII would lead to increased activity.A study of extended acid side chains at C-5 of the imidazole nucleus led to the discovery of the (E)-acrylic acid 5 as a promising starting point for further exploration.As predicted by the modeling, substitution of a benzyl group on the acrylic acid side chain to mimic the phenylalanine gave increased potency.An extensive study of the SAR of the newly introduced aromatic ring revealed that electron-rich heteroaryl rings provided improved activity, most notably in the in vivo rat models.Compound 40, (E)-3-imidazol-5-yl>-2--2-propenoic acid, has been shown to be a potent, competitive, and orally active small molecule AT-1 receptor antagonist.It exhibits a 2 orders of magnitude increase in binding affinity and a 10-fold improvement in in vivo potency as compared to compound 1 and represents an important milestone in the development of even more potent nonpeptide angiotensin II receptor antagonists.
