Solid-Phase Synthesis of 1,2,3,4-Tetrahydro-2-pyridones via Aza-Annulation of Enamines
- 30 August 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (19) , 6160-6166
- https://doi.org/10.1021/jo000676c
Abstract
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 α,β-unsaturated acid anhydrides or α,β-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 α- and β-substituted acrylic acid derivatives on the annulation reaction was also investigated.Keywords
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