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The transformation of 2-imidazolines into 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines has been realized. A pseudo-three-component reaction of 2-imidazolines with terminal electron-deficient alkynes (2 equiv) first generates imidazolidines, containing an N-vinylpropargylamine fragment. The latter can then undergo a base-catalyzed domino aza-Claisen rearrangement/cyclization reaction sequence, simultaneously constructing pyrrole and pyrazine rings. The process works in a broad substrate scope, delivering pyrrolo[1,2-a]pyrazines in good to excellent yields (45-90%). This two-step approach can be carried out in a one-pot fashion without a noticeable decrease in yield. Remarkably, a three-component protocol for the introduction of two different alkynes has been also developed.

Citation

Nikita E Golantsov, Alexandra S Golubenkova, Alexey A Festa, Alexey V Varlamov, Leonid G Voskressensky. Assembly of 1,2,3,4-Tetrahydropyrrolo[1,2-a]pyrazines via the Domino Reaction of 2-Imidazolines and Terminal Electron-Deficient Alkynes. The Journal of organic chemistry. 2022 Mar 04;87(5):3242-3253

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PMID: 35049314

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