

NUCLEOPHILIC DEAROMATIZATION OF 3-NITROBENZOFURANS BY THE ACTION OF 2-(1-ARYLETHYLIDENE)MALONONITRILES

Abstract
When 2-(1-arylethylidene)malononitriles act upon 3-nitrobenzofurans in the presence of triethylamine, the furan ring opens and triethylammonium 2-aryl-1,1-dicyano-5-nitropenta-2,4-dien-1-ides are formed. The obtained salts containing the chromophoric 1,1-dicyanopentadienide fragment are of interest as anionic polymethine dyes.
Keywords
2-(1-arylethylidene)malononitriles; 1,1-dicyanopenta-2,4-dien-1-ide anion; 3-nitrobenzofurans; Michael reaction; nucleophilic dearomatization.
Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv