1,4-Dihydropyrrolo[3,2-<i>b</i>]pyrroles with Two Embedded Heptagons via Alkyne Annulation
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 <i>6-endo-dig</i> attack of a protonated alkyne at the position 3a of pyrrolopyrrole followed by a 1,2-vinyl shift.
Authors
- Gana Sanil (ORCID: https://orcid.org/0000-0001-7570-0544)
- Wojciech Chaładaj (ORCID: https://orcid.org/0000-0001-8143-3788)
- Denis Jacquemin (ORCID: https://orcid.org/0000-0002-4217-0708)
- Łukasz Dobrzycki (ORCID: https://orcid.org/0000-0002-4426-963X)
- Michał K. Cyrański (ORCID: https://orcid.org/0000-0003-1277-6124)
- Daniel T. Gryko (ORCID: https://orcid.org/0000-0002-2146-1282)
Institutions
- Centre National de la Recherche Scientifique (FR)
- Institut Universitaire de France (FR)
- Institute of Organic Chemistry (PL)
- Chimie et Interdisciplinarité, Synthèse, Analyse, Modélisation (FR)
- University of Warsaw (PL)
- Nantes Université (FR)
- Polish Academy of Sciences (PL)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-12-31
- DOI
- https://doi.org/10.1021/acs.joc.4c02538
- Citations
- 2
- Primary Topic
- Synthesis and Characterization of Pyrroles
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- European Commission
- Narodowe Centrum Nauki
- Uniwersytet Warszawski
- H2020 Marie Skłodowska-Curie Actions