1,4-Dihydropyrrolo[3,2-b]pyrroles with Two Embedded Heptagons via Alkyne Annulation

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dc.contributor.authorGana Sanil
dc.contributor.authorDobrzycki, Łukasz
dc.contributor.authorCyrański, Michał K.
dc.contributor.authorJacquemin, Denis
dc.contributor.authorChaładaj, Wojciech
dc.contributor.authorGryko, Daniel T.
dc.contributor.organizationInstitute of Organic Chemistry, Polish Academy of Sciences
dc.contributor.organizationFaculty of Chemistry, University of Warsaw
dc.contributor.organizationNantes Université, CNRS, France
dc.contributor.organizationInstitut Universitaire de France
dc.date.accessioned2025-01-28T16:02:19Z
dc.date.available2025-01-28T16:02:19Z
dc.date.issued2025
dc.description.abstractDrastic 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.en
dc.description.sponsorshipEuropean Union’s Horizon 2020 research and innovation programme under the Marie Skłodowka-Curie grant agreement No. 860762; Polish National Science Center, grants OPUS 2020/37/B/ST4/00017; Wroclaw Centre for Networking and Supercomputing, grant no. 518; Maria Skłodowska-Curie and Pierre Curie Polish-French Science Award.
dc.identifier.citationJ. Org. Chem. 2025, 90, 1, 614–622 // https://doi.org/10.1021/acs.joc.4c02538
dc.identifier.doi10.1021/acs.joc.4c02538
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.urihttps://open.icm.edu.pl/handle/123456789/25322
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 Międzynarodoween
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/
dc.sourceJournal of Organic Chemistry
dc.title1,4-Dihydropyrrolo[3,2-b]pyrroles with Two Embedded Heptagons via Alkyne Annulationen
dc.typearticle
dc.type.versionpublishedVersion
person.identifier.orcidChaładaj, Wojciech [0000-0001-8143-3788]
person.identifier.orcidGryko, Daniel T. [0000-0002-2146-1282]
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