Concise Approach towards Tetramic Acid Derivatives via Ugi Reaction/Dieckmann Cyclization Sequence

Author:

Guranova Natalia1,Bakulina Olga1,Kantin Grigory1,Dar'in Dmitry12

Affiliation:

1. Institute of Chemistry Saint Petersburg State University Saint Petersburg 199034 Russian Federation

2. Saint Petersburg Research Institute of Phthisiopulmonology Saint Petersburg 191036 Russian Federation

Abstract

AbstractTetramic acids exhibit intriguing biological activity and are particularly attractive scaffolds for drug design. In this paper, we present a convenient approach based on the Dieckmann cyclization of Ugi adducts of malonic monoesters to afford a series of medically important polysubstituted tetramic acid derivatives. This simple and versatile method tolerates various substituents in both the amine, aldehyde and isocyanide moieties allowing the use of α‐substituted malonic acid monoesters. Examples of further functionalization of the free methylene group in the synthesized compounds have been presented.

Funder

Russian Science Foundation

Publisher

Wiley

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