Yu Zheng, Gongli Yu, Jinlong Wu
Apr 1, 2010
Citations
0
Influential Citations
1
Citations
Journal
Synlett
Abstract
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 2 CO 3 in DMA at 120 °C and underwent an intramolecular direct arylation using Pd(OA C ) 2 -dppf, furnishing the 5,6-dihydrophenanthridine derivative. In contrast, the corresponding phenyl oxanilates decomposed upon exposure to K 2 CO 3 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 (NO 2 , Cl) and weak electron-donating (Me) substituents provided the N-arylisoindolin-1-ones in 43-80% yields.