Abstract
From 2-aminonorbornene hydroxamic acids, a simple and efficient method for the preparation of pyrrolo[1,2-a]pyrimidine enantiomers is reported. The synthesis is based on domino ring-closure followed by microwave-induced retro Diels-Alder (RDA) protocols, where the chirality of the desired products is transferred from norbornene derivatives. The stereochemistry of the synthesized compounds was proven by X-ray crystallography. The absolute configuration of the product is determined by the configuration of the starting amino hydroxamic acid.
Highlights
The first hydroxamic acid was discovered by Lossen as early as 1869.hydroxamic acids attracted further attention at the beginning of the 1980s because of their bioactivity [2]
Focusing on the biological potential of fused quinazolinones, and continuing our work on the synthesis of novel N-heterocycles, we report the synthesis of a new series of pyrrolo[1,2-a]
New racemic and enantiomeric pyrrolo[1,2-a]pyrimidines were synthesized starting from diendo- and diexo-2-aminonorbornene hydroxamic acids
Summary
Hydroxamic acids attracted further attention at the beginning of the 1980s because of their bioactivity [2]. Their pharmacological properties are related to their ability to scavenge metal ions [3]. They are able to generate nitric oxide [3,4,5] in living systems. They can act as antimicrobial [6,7,8,9], antitumour [6,10], antihypertensive [11], anti-inflammatory [6,12], and neuroleptic agents, among others [3,13].
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