Synthesis of Thieno[3,2- e ][1,4]diazepin-2-ones: Application of an Uncatalysed Pictet-Spengler Reaction - Université de Montpellier Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2015

Synthesis of Thieno[3,2- e ][1,4]diazepin-2-ones: Application of an Uncatalysed Pictet-Spengler Reaction

Résumé

A series of 5-substituted thieno[3,2-e][1,4]diazepin-2-ones was synthesized in four steps from methyl 3-aminothiophene-2-carboxylate. After the coupling of 3-aminothiophene with α-amino acids, the key final step that involves an uncatalysed Pictet–Spengler reaction allowed the cyclization of the seven-membered diazepinone ring. The reaction was first optimized and then exemplified in three different series (phenylalanine, alanine and proline) that led to 24 target diazepinones, which includes 19 optically pure diastereomers.

Domaines

Chimie

Dates et versions

hal-03563932 , version 1 (10-02-2022)

Identifiants

Citer

Séverine Denoyelle, Guillaume Tambutet, Nicolas Masurier, Ludovic Maillard, Jean Martinez, et al.. Synthesis of Thieno[3,2- e ][1,4]diazepin-2-ones: Application of an Uncatalysed Pictet-Spengler Reaction. European Journal of Organic Chemistry, 2015, 2015 (32), pp.7146-7153. ⟨10.1002/ejoc.201500943⟩. ⟨hal-03563932⟩
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