1,4-Dihydropyrrolo[3,2-b]pyrroles with Two Embedded Heptagons via Alkyne Annulation
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1,4-Dihydropyrrolo[3,2-b]pyrroles with Two Embedded Heptagons via Alkyne Annulation.pdf (3.55 MB)
0000-0001-8143-3788 Date
2025
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American Chemical Society
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Abstract
Drastic changes to the character of the acidic catalyst enable the reversal of the double alkyne benzannulation reaction output. In the presence of a strong Brønsted acid, 1,4-dihydropyrrolopyrroles undergo transformation which results in the formation of two 7-membered rings. Computational studies imply that the thermodynamically unfavored 7-membered ring is forged via the kinetically favored 6-endo-dig attack of a protonated alkyne at the position 3a of pyrrolopyrrole followed by a 1,2-vinyl shift.
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J. Org. Chem. 2025, 90, 1, 614–622 // https://doi.org/10.1021/acs.joc.4c02538