Synthesis of fused tetramate-oxazolidine and -imidazolidine derivatives and their antibacterial activity?

Organic & Biomolecular Chemistry Pub Date: 2023-05-26 DOI: 10.1039/D3OB00594A

Abstract

A chemoselective route which provides direct access to bicyclic tetramates, making use of Dieckmann cyclisation of functionalised oxazolidines and imidazolidines derived from an aminomalonate, is reported; calculations suggest that the observed chemoselectivity is kinetically controlled and leads to the thermodynamically most stable product. Some compounds in the library showed modest antibacterial activity against Gram-positive bacteria, and this activity is maximal in a well-defined region of chemical space (554 < Mw < 722 g mol?1; 5.78 < cLogP < 7.16; 788 < MSA < 972 ?2; 10.3 < rel. PSA < 19.08).

Graphical abstract: Synthesis of fused tetramate-oxazolidine and -imidazolidine derivatives and their antibacterial activity
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