136741-51-0Relevant academic research and scientific papers
A divergent and selective synthesis of isomeric benzoxazoles from a single N-Cl imine
Chen, Cheng-Yi,Andreani, Teresa,Li, Hongmei
, p. 6300 - 6303 (2012/01/05)
A divergent and regioselective synthesis of either 3-substituted benzisoxazoles or 2-substituted benzoxazoles from readily accessible ortho-hydroxyaryl N-H ketimines is described. The reaction proceeds in two distinct pathways through a common N-Cl imine intermediate: (a) N-O bond formation to form benzisoxazole under anhydrous conditions and (b) NaOCl mediated Beckmann-type rearrangement to form benzoxazole, respectively. The reaction path also depends on the electronic nature of the aromatic ring, with the electron-rich aromatic rings favoring the rearrangement and the electron-deficient rings favoring the N-O bond formation. A Beckmann-type rearrangement mechanism via net [1,2]-aryl migration for the formation of 2-substituted benzoxazole is proposed.
Studies on uricosuric diuretics. II. Substituted 7,8-dihydrofuro[2,3-g]-1,2-benzisoxazole-7-carboxylic acids and 7,8-dihydrofuro[2,3-g]benzoxazole-7-carboxylic acids
Sato,Dan,Onuma,Tanaka,Aoki,Koga
, p. 1760 - 1772 (2007/10/02)
A series of substituted 7,8-dihydrofuro[2,3-g]-1,2-benzisoxazole-7-carboxylic acids and 7,8-dihydrofuro[2,3-g]benzoxazole-7-carboxylic acids were synthesized and evaluated for uricosuric and diuretic activities in rats. Many of the benzisoxazole derivatives showed uricosuric and only weak diuretic activities, whereas the benzoxazoles exhibited potent diuretic activities with little affecting urate excretion. Among these compounds, 5-chloro-7,8-dihydro-3-phenylfuro[2,3-g]-1,2-benzisoxazole-7-carboxylic acid (AA-193) was found to be a potent uricosuric agent without diuretic activity and was selected for further development.
