1156766-73-2Relevant academic research and scientific papers
Synthesis of N -arylisoindolin-1-ones via pd-catalyzed intramolecular decarbonylative coupling of N -(2-bromobenzyl)oxanilic acid phenyl esters
Zheng, Yu,Yu, Gongli,Wu, Jinlong,Dai, Wei-Min
scheme or table, p. 1075 - 1080 (2010/08/06)
Ethyl and phenyl oxanilates were readily prepared from N-(2-bromobenzyl) anilines and oxalyl chloride monoethyl and monophenyl esters, respectively. It was found that the ethyl oxanilate survived in the presence of K 2CO3 in DMA at 120°C and underwent an intramolecular direct arylation using Pd(OAc)2-dppf, furnishing the 5,6-dihydrophenanthridine derivative. In contrast, the corresponding phenyl oxanilates decomposed upon exposure to K2CO3 in DMA at 120 C and were transformed into N-arylisoindolin-1-ones via Pd(OAc) 2-dppf-catalyzed intramolecular decarbonylative coupling. Except for the 4-methoxy-substituted oxanilic acid phenyl ester, other phenyl oxanilates possessing electron-withdrawing (NO2, Cl) and weak electron-donating (Me) substituents provided the N-arylisoindolin-1-ones in 43-80% yields.
