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

Year: 2024
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide 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.
DOI: 10.1021/acs.joc.4c02538
Authors: Gana Sanil, Łukasz Dobrzycki, Michał K. Cyrański, Denis Jacquemin, Wojciech Chaładaj, Daniel T. Gryko
Institutions: Institute of Organic Chemistry, Polish Academy of Sciences, University of Warsaw, Centre National de la Recherche Scientifique, Institut Universitaire de France, Chimie et Interdisciplinarité, Synthèse, Analyse, Modélisation, Nantes Université
Language: English
Field: Chemistry
Open Access status: hybrid
Estimated APC paid: $4,500
OpenAlex ID: W4405956342
FWCI: 0.419
Cites: 48
Cited by: 3
Related to: 10