Journal
MOLECULES
Volume 27, Issue 16, Pages -Publisher
MDPI
DOI: 10.3390/molecules27165257
Keywords
acyl(quinoxalin-2-yl)ketene; cycloaddition; cyanamide; heterocumulene; hetero-Diels-Alder reaction; 4H-1; 3-oxazine; thermolysis
Funding
- Ministry of Science and Higher Education of the Russian Federation [FSNF-2020-0008]
- Russian Foundation for Basic Research [20-43-596008]
- government of Perm Krai
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A diversity-oriented approach based on the hetero-Diels-Alder reaction was developed to synthesize a series of skeletally diverse 4H-1,3-oxazines. These compounds, obtained by reacting 4-acyl-1H-pyrrole-2,3-diones fused with cyanamides, show potential inhibitory activities against anticancer targets.
4-Acyl-1H-pyrrole-2,3-diones fused at [e]-side with a heterocyclic moiety are suitable platforms for the development of a hetero-Diels-Alder-reaction-based, diversity-oriented approaches to series of skeletally diverse heterocycles. These platforms are known to react as oxa-dienes with dienophiles to form angular 6/6/5/6-tetracyclic alkaloid-like heterocycles and are also prone to decarbonylation at high temperatures resulting in generation of acyl(imidoyl)ketenes, bidentate aza- and oxa-dienes, which can react with dienophiles to form skeletally diverse products (angular tricyclic products or heterocyclic ensembles). Based on these features, we have developed an approach to two series of skeletally diverse 4H-1,3-oxazines (tetracyclic alkaloid-like 4H-1,3-oxazines and 5-heteryl-4H-1,3-oxazines) via a hetero-Diels-Alder reaction of 4-acyl-1H-pyrrole-2,3-diones fused at [e]-side with cyanamides. The products of these transformations are of interest for drug discovery, since compounds bearing 4H-1,3-oxazine moiety are extensively studied for inhibitory activities against anticancer targets.
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