α-Acetylstyrylphosphonates were conveniently synthesized from 2-oxopropylphosphonates and substituted (dimorpholinomethyl)-benzenes (aminals). 4-Benzylidenemorpholinium carboxylates, generated from aminals by the action of α-halo acids, reacted with the phosphonates to give the products by elimination of the amine. The yields were influenced by the nature of substituents and their position in the phenyl ring and could be improved by adjustment of the acidities of the reacted acids. α-Acetylstyrylphosphonates containing various substituents on every position (at the 2-, 3-, or 4-position) in the phenyl ring were obtained generally in excellent yields using monochloroacetic acid.
A NEW PROTOCOL FOR THE PREPARATION OF AMINALS FROM AROMATIC ALDEHYDES AND THEIR FACILE CONVERSION TO PHOSPHONATES
作者:Mohammad Karimi Dezfuli、Mohammad Reza Saidi
DOI:10.1080/10426500490257078
日期:2004.1
A new and fast method for the preparation of aminals is reported from the reaction of aromaticaldehydes and secondary amines in the presence of potassium carbonate in high yields. The aminal can be converted to the corresponding iminum salt in reaction with acetyl chloride very easily and in very short time with high yield. Addition of trialkylphosphite, as one possible nucleophile, to the prepared