Solid-phase Mannich condensation of amines, aldehydes, and alkynes: investigation of diverse aldehyde inputs.
Terminal alkynes, secondary amines, and aldehydes undergo "solid-phase Mannich condensation". A set of diverse aldehyde inputs was examined. Aliphatic, aralkyl, aryl, and heteroaryl carboxaldehydes give good yields of Mannich adduct of high purity. Benzaldehydes containing electron-donating substituents that decrease the electrophilicity of the carbonyl center, or heteroaryl aldehydes that are similarly deactivated by resonance effects, do not undergo reaction.
Youngman
M A
MA
Drug Discovery, The R. W. Johnson Pharmaceutical Research Institute, Spring House, Pennsylvania 19477-0776, USA.
Dax
S L
SL
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry*; D000480:Alkynes / Q000138:chemical synthesis*; D000588:Amines / Q000138:chemical synthesis*; D001547:Benzaldehydes / Q000138:chemical synthesis / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D008352:Mannich Bases / Q000737:chemistry; D013058:Mass Spectrometry
D000447:Aldehydes; D000480:Alkynes; D000588:Amines; D001547:Benzaldehydes; D008352:Mannich Bases