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Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins.

ABSTRACT: A practical three-step protocol for the assembly of triazolobenzodiazepine-fused diketopiperazines and hydantoins has been developed. The synthesis of these tetracyclic ring systems was initiated by an Ugi reaction, which brought together all necessary functionalities for further transformations. The Ugi adducts were then subjected to a base-induced ring closing and an intramolecular azide-alkyne cycloaddition reaction in succession to obtain highly fused benzodiazepine frameworks.

SUBMITTER: Vroemans R

PROVIDER: S-EPMC5870159 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins.

Vroemans Robby R Bamba Fante F Winters Jonas J Thomas Joice J Jacobs Jeroen J Van Meervelt Luc L John Jubi J Dehaen Wim W

Beilstein journal of organic chemistry 20180314

A practical three-step protocol for the assembly of triazolobenzodiazepine-fused diketopiperazines and hydantoins has been developed. The synthesis of these tetracyclic ring systems was initiated by an Ugi reaction, which brought together all necessary functionalities for further transformations. The Ugi adducts were then subjected to a base-induced ring closing and an intramolecular azide-alkyne cycloaddition reaction in succession to obtain highly fused benzodiazepine frameworks. ...[more]

PMID: 29623124

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