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Article Dans Une Revue European Journal of Organic Chemistry Année : 2015

Synthetic Route to Rare Isoindolones Derivatives

Résumé

A shorter and more versatile synthetic route has been developed to prepare tetrahydropyrido[2,1‐a]isoindolone and superior analogues. The key step of this synthesis is the formation of the lactam ring by a cyclization using Shibasaki's conditions. The isoindolone scaffold is present in many biologically active compounds. Here, we have developed a shorter and more efficient synthesis of tetrahydropyrido[2,1‐a]isoindolone. The key step of this approach is a cyclization to form the γ‐lactam ring under Shibasaki's conditions. Thus, tetrahydropyrido[2,1‐a]isoindolone and superior analogues, namely hexahydroazepino[2,1‐a]isoindolone and hexahydroazocino[2,1‐a]isoindolone, have been prepared in only three steps in 39, 25, and 19 % overall yields, respectively. This novel strategy offers a shorter alternative to existing procedures.

Dates et versions

hal-01150276 , version 1 (10-05-2015)

Identifiants

Citer

Killian Oukoloff, Frederic Buron, Sylvain Routier, Ludovic Jean, Pierre-Yves Renard. Synthetic Route to Rare Isoindolones Derivatives. European Journal of Organic Chemistry, 2015, 2015 (11), pp.2450-2456. ⟨10.1002/ejoc.201403649⟩. ⟨hal-01150276⟩
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