173904-10-4Relevant articles and documents
The use of Lewis acids in the synthesis of 5-arylhydantoins
Cativiela, Carlos,Fraile, Jose M.,Garcia, Jose I.,Lafuente, Gustavo,Mayoral, Jose A.,Tahir, Rachid,Pallares, Antonio
, p. 192 - 196 (2004)
Different Lewis acids are able to promote the Friedel-Crafts reaction between 5-bromohydantoin and aromatic compounds. In the case of phenol, mixtures of ortho and para isomers are always obtained, with Mg(ClO4) 2 leading to the best selectivity. However, the best overall yield of 5-(hydroxyphenyl)hydantoin is obtained with YbCl3. This method can be extended to other aromatic systems such as anisole and thiophene. These reactions give similar yields but proceed with total selectivity to 5-(4-methoxyphenyl)hydantoin and 5-(2-thiophenyl)hydantoin, respectively. The cationic exchange of MgII and YbIII on anionic solid supports allows the preparation of very efficient heterogeneous catalysts for this reaction (productivity up to 600 mol of hydantoin per mole of Mg). These catalysts have practical advantages in that they can be recycled and reused.
Synthesis of parazoanthine B and analogs
Tinto, Francesco,Pagano, Dario,Manzo, Emiliano
, p. 4379 - 4384 (2015/06/08)
A versatile synthesis of the natural product parazoanthine B (2) and its analogs, parazoanthine C (3) and 18-deoxy-parazoanthine B (4), has been accomplished by a key coupling reaction between a hydantoinic compound and an α-bromo-acetophenone derivative. The synthetic approach is designed to address preparation of a wider group of parazoanthine B analogs characterized by the presence of the 5,6-double bond of Z-configuration.
Benzoxazoline and benzimidazoline derivatives as novel aldose reductase inhibitors, part 1: Lead evolution
Nakao, Kazuya,Asao, Masaaki,Shirai, Hiroki,Saito, Kiyoshi,Moriya, Tamon,Iwata, Hiroshi,Matsumoto, Mamoru,Matsuoka, Yuzo,Shimizu, Ryo
, p. 621 - 630 (2007/10/03)
Based on the 3D-pharmacophore model of aldose reductase inhibitors obtained by 3D-QSAR and protein-ligand docking study of spiroquinazolinones, we designed novel benzoxazoline and benzimidazoline derivatives. These compounds exhibited high potency enough to be promising as leads for further optimization.
