25631-82-7Relevant articles and documents
Further Insight into the Castagnoli-Cushman-type Synthesis of 1,4,6-Trisubstituted 1,6-Dihydropyridin-2-(3 H)-ones from 3-Arylglutaconic Acid Anhydrides
Firsov, Andrei,Bakulina, Olga,Dar'in, Dmitry,Guranova, Natalia,Krasavin, Mikhail
, p. 6822 - 6829 (2020)
The earlier reported three-component Castagnoli-Cushman-type synthesis of 1,4,6-trisubstituted 1,6-dihydropyridin-2-(3H)-ones from 3-arylglutaconic acids, primary amines, and aromatic aldehydes has been further investigated. It was shown to proceed via 3-arylglutaconic anhydrides, which, in turn, were found to give superior results in the two-component reactions with imines. The initial formation of the Castagnoli-Cushman carboxylic acids was shown to be the case, and their decarboxylation was found to follow a complex, forked pathway, which was confirmed by deuterium incorporation experiments.
Carboxylative Cyclization of 2-Butenoates with Carbon Dioxide: Access to Glutaconic Anhydrides
Zhang, Ke,Zhang, Wen-Zhen,Tao, Xue-Yan,Zhang, Min,Ren, Wei-Min,Lu, Xiao-Bing
, p. 11579 - 11588 (2020/10/12)
Cyclic anhydrides are versatile synthons and functional comonomers. Herein, we reported an organic base-promoted carboxylative cyclization of 2-butenoates with carbon dioxide to produce important glutaconic anhydrides in good yields. This metal-free react
Catalytic asymmetric tamura cycloadditions
Manoni, Francesco,Connon, Stephen J.
, p. 2628 - 2632 (2014/03/21)
In the presence of a novel, tert-butyl-substituted squaramide-based catalyst, enolizable anhydrides react with alkylidene oxindoles to generate spirooxindole products of significant synthetic interest with excellent enantio- and diastereocontrol. The methodology is of wide scope and encompasses both homophthalic and glutaconic anhydride derivatives, which lead to structurally diverse products. Glutaconic acid-derived anhydrides undergo a clean post-cyclization decarboxylation process which is not a feature of reactions involving homophthalic acid-derived anhydrides. The unusual influence of reaction temperature on diastereocontrol has been probed, with reactions occurring at 30 °C and -30 °C delivering products epimeric at one stereocenter only, in near optical purity. Squared away: The first strategy for bringing about enantioselective Tamura reactions is reported. In the presence of a squaramide-based catalyst, enolizable anhydrides react with alkylidene oxindoles to generate spirooxindole products with excellent enantio- and diastereocontrol. The methodology is of wide scope and leads to structurally diverse products.