Synthesis and reactivity of pyrrolo[3,2-d][1,3]oxazine-2,4-dione. Access to new pyrrolo[3,2-e][1,4]diazepine-2,5-diones - Université de Montpellier
Article Dans Une Revue Tetrahedron Année : 2014

Synthesis and reactivity of pyrrolo[3,2-d][1,3]oxazine-2,4-dione. Access to new pyrrolo[3,2-e][1,4]diazepine-2,5-diones

Résumé

A convenient synthesis of pyrrolo[3,2-d][1,3]oxazine-2,4-dione 4 is described and its reactivity towards various nucleophiles studied. The regioselective ring opening of anhydride 4 or its N-alkylated analog 25 in the presence of alanine or proline afforded, respectively, imidazolidinedione 22 and N-protected pyrrolo[3,2-e][1,4]diazepines 30 and 31 in a one-pot process. In a last part of this study, an alternative route to produce a library of eight non protected pyrrolo[3,2-e][1,4]diazepine-2,5-diones 35a–h is described to overcome the limited reactivity of anhydride 4.

Domaines

Chimie
Fichier non déposé

Dates et versions

hal-03563449 , version 1 (09-02-2022)

Identifiants

Citer

Jean-Daniel Malcor, Yann Brouillette, Julien Graffion, Kim Spielmann, Nicolas Masurier, et al.. Synthesis and reactivity of pyrrolo[3,2-d][1,3]oxazine-2,4-dione. Access to new pyrrolo[3,2-e][1,4]diazepine-2,5-diones. Tetrahedron, 2014, 70 (31), pp.4631-4639. ⟨10.1016/j.tet.2014.05.046⟩. ⟨hal-03563449⟩
13 Consultations
0 Téléchargements

Altmetric

Partager

More