Solid-Phase Synthesis of 1,2,3,4-Tetrahydro-2-pyridones via Aza-Annulation of Enamines

Citations Over Time

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 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.

Related Papers

• → Synthesis of Natural Products, Carbocycles, and Heterocycles by Hauser–Kraus Annulation(2023)13 cited
• → π-Conjugated carbocycles and heterocycles via annulation through C-H and X-Y activation across CC triple bonds(2015)4 cited
• → [4 + 2] Annulation of Activated o-Toluate/o-Tolualdehyde Donors (Hauser-Leusen Annulation)(2018)1 cited
• → [4 + 2] Annulation With Nonactivated o-Toluate Donors (Staunton-Weinreb-Myers Annulation)(2018)
• → ИСПОЛЬЗОВAНИЕ ПОТЕНЦИAЛA СОЦИAЛЬНЫХ ПAРТНЕРОВ В ПОДГОТОВКЕ БУДУЩИХ ПЕДAГОГОВ(2024)