91616-28-3Relevant academic research and scientific papers
Boronic acid catalysis for mild and selective [3+2] dipolar cycloadditions to unsaturated carboxylic acids
Zheng, Hongchao,McDonald, Robert,Hall, Dennis G.
experimental part, p. 5454 - 5460 (2010/09/15)
Herein, the concept of boronic acid catalysis (BAC) for the activation of unsaturated carboxylic acids is applied in several classic dipolar [3 + 2] cycloadditions involving azides, nitrile oxides, and nitrones as partners. These cycloadditions can be used to produce pharmaceutically interesting, small heterocyclic products, such as triazoles, isoxazoles, and isoxazolidines. These cycloadducts are formed directly and include a free carboxylic acid functionality that can be employed for fur-ther transformations, thereby avoiding prior masking or functionalization. In all cases, BAC provides faster reactions, under milder conditions, with much improved product yields and regioselectivities. In some instances, such as triazole formation from the reaction of azides with 2-alkynoic acids, catalysis with ort/io- nitrophenylboronic acid circumvents the undesirable product decarboxylation observed when using thermal activation. By using NMR spectroscopic studies, the boronic acid catalyst was shown to provide activation by a LUMO-lowering effect in the unsaturated carboxylic acid, likely via a monoacylated hemiboronic ester intermediate.
On the reactivity of activated alkynes in copper and solvent-free Huisgens reaction
Elamari, Hichem,Jlalia, Ibtissem,Louet, Charlotte,Herscovici, Jean,Meganem, Faouzi,Girard, Christian
scheme or table, p. 1179 - 1183 (2010/11/02)
Terminal alkynes substituted by a carbonyl-type electron-withdrawing group have been found to undergo Huisgens cycloaddition with azides at room temperature in a solvent-free manner; without a need of either heating or catalysis. Metallic salts, other tha
Regioselective synthesis of [1,2,3]-triazoles catalyzed by Cu(I) generated in situ from Cu(0) nanosize activated powder and amine hydrochloride salts
Orgueira, Hernán A.,Fokas, Demosthenes,Isome, Yuko,Chan, Philip C.-M.,Baldino, Carmen M.
, p. 2911 - 2914 (2007/10/03)
A straightforward and efficient method for the regioselective synthesis of functionalized 1,4-disubstituted [1,2,3]-triazoles, from terminal alkynes and azides, has been established utilizing Cu(0) as the source of the catalytic species. The presumed cata
CHINAZOLINE DERIVATIVES AS AURORA KINASE INHIBITORS
-
Page 50, (2010/02/10)
Quinazoline derivatives of formula (I) (A chemical formula should be inserted here - please see paper copy enclosed herewith) formula (I) for use in the treatment of proliferative diseases such as cancer and in the preparation of medicaments for use in th
