Abstract
Dihydropyrrolo[1,2-a]pyrazinone rings are a class of heterocycles present in a wide range of bioactive natural products and analogues thereof. As a direct result of their bioactivity, the synthesis of this privileged class of compounds has been extensively studied. This review provides an overview of these synthetic pathways. The literature is covered up until 2020 and is organized according to the specific strategies used to construct the scaffold: fusing a pyrazinone to an existing pyrrole, employing a pyrazinone-first strategy, an array of multicomponent reactions and some miscellaneous reactions.
Highlights
Nitrogen-containing heteroaromatic rings are valuable motifs in bioactive molecules and recurrent scaffolds present in drugs [1,2]
Dihydropyrrolo[1,2-a]pyrazinone rings are found in the structure of a number of bioactive compounds, including synthetic and natural products isolated from various sources like fungi, plants or sponges
A similar aza-Michael cyclization was reported in the total synthesis a]pyrazinones, in comparison to a recent general overview of the eight different pyrroloof longamide B and cyclooroidin via the Wadsworth–Horner–Emmons olefination of lactam isomers [31]
Summary
Nitrogen-containing heteroaromatic rings are valuable motifs in bioactive molecules and recurrent scaffolds present in drugs [1,2]. Dihydropyrrolo[1,2-a]pyrazinone rings are found in the structure of a number of bioactive compounds, including synthetic and natural products isolated from various sources like fungi, plants or sponges. These natural products (some structures are shown in Figure 1) often contain one or two bromine substituents on the pyrrole ring. We will cover the different synthetic strategies leading to the dihydropyrrolopyrazinone scaffold These include (1) the fusion of a pyrazinone to a pyrrole derivative, (2) the fusion of a pyrrole to a pyrazinone, (3) multicomponent reactions and (4) miscellaneous strategies.
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