Synthesis of 3-substituted indolizidines from amino-ynones derivatives

Huy-Dinh Vu (1, 2) , Jacques Renault (1) , Thierry Roisnel (1) , Nicolas Gouault (1) , Philippe Uriac (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 Department of Chemistry

Two types of indolizidine derivatives can be synthesized from amino-ynones. In the presence of methanesulfonic acid, Meyer-Schuster rearrangement furnished vinylogues of indolizidin-3-ones whereas treatment with zinc chloride gave stable 3-alkynyl-1,5,6,7,8,8a-hexahydroindolizine-zinc complexes that were reduced to 3-alkynylindolizidines.

Keywords: Amino-ynone; Indolizidine; Methanesulfonic acid; Zinc chloride

Domains: Chemical Sciences; Organic chemistry

Huy-Dinh Vu, Jacques Renault, Thierry Roisnel, Nicolas Gouault, Philippe Uriac. Synthesis of 3-substituted indolizidines from amino-ynones derivatives. Tetrahedron Letters, 2016, 57 (27-28), pp.3036--3038. ⟨10.1016/j.tetlet.2016.05.108⟩. ⟨hal-01334050⟩