Metal template reactions. X. Improved syntheses of 2,2'-(Ethane-1,2-diyldiimino) bisbenzaldehyde and 2,2'-(Propane-1,3-diyl-diimino)bisbenzaldehyde

Abstract

2,2'-(Propane-1,3-diyldiimino)bisbenzaldehyde (2) has been synthesized by a high-yielding route involving the alkylation of the isatin anion with 1,3-dibromopropane. 2,2'-(Ethane-1,2-diyldiimino)-bisbenzaldehyde (1) can be synthesized most effectively by a route involving initial acylation of methyl anthranilate with oxalyl chloride. Subsequent reductive and oxidative transformations are then carried out in each case.