73750-43-3Relevant academic research and scientific papers
THE MICHAEL ADDITION OF ENAMINES TO PROPENAMIDINES. A CONVENIENT SYNTHESIS OF 2-β-AMIDINOETHYLCYCLOALKANONES BY AMIDINOETHYLATION REACTION
Fuks, Robert,Bril, Marc Van den
, p. 1681 - 1696 (2007/10/02)
A variety of propenamidines 3 have been reacted with enamines of cyclopentanone and cyclohexanone giving after hydrolysis of the Stork enamine 6, 2-β-amidinoethylcyclopentanones 8 and -hexanones 7.This reaction illustrates the electrophilic character of the C=C double bond due to the conjugated amidine function, thus providing with propenamidines 3 a new class of Michael acceptors for enamines.
SYNTHESE DE NOUVELLES PROPENAMIDINES N-SUBSTITUEES A PARTIR DE SELS DE NITRILIUM
Bril, Marc Van Den,Fuks, Robert
, p. 433 - 440 (2007/10/02)
A number of N-t-butylpropenamidines V have been prepared for the first time by amination of N-t-butylacrylonitrilium (IIIb) or N-t-butylmethacrylonitrilium tetrachloroferrate (IIIc).The salts IIIb and IIIc are easily prepared at -40 deg C within a few minutes from the corresponding nitrile, t-butyl chloride and ferric chloride.The amination (with primary or secondary aliphatic or aromatic amines) should be started at -70 deg C to ensure a smooth reaction and to give high yields of amidine V, because the nitrilium salts are unstable above -10 deg C.This method represents an easy one-pot synthesis of N-t-butyl substituted propenamidines from the corresponding nitrile I.
