Solid-phase synthesis of 1,2,3,4-tetrahydro-2-pyridones via aza-annulation of enamines.
An efficient solid-phase approach has been developed to prepare nitrogen heterocycles with a 1,2,3,4-tetrahydro-2-pyridone core via aza-annulation of enamines. Immobilized enamines were prepared from the reaction of primary amines with propynoic acid derivatives or ketones. Aza-annulation reactions were carried out by reacting resin-bound enamines with symmetrical alpha,beta-unsaturated acid anhydrides or alpha,beta-unsaturated acids in the presence of DPPA and TEA. The annulation products were isolated in good to high crude yields. Influence of sterically hindered amines as well as alpha- and beta-substituted acrylic acid derivatives on the annulation reaction was also investigated.
Paulvannan
K
K
Affymax Research Institute, 3410 Central Expressway, Santa Clara, California 95051, USA. kumar_paulvannan@affymax.com
Chen
T
T
D000588:Amines / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011728:Pyridones / Q000138:chemical synthesis*
D000588:Amines; D001372:Aza Compounds; D011728:Pyridones