Convenient Access to 2,3-Disubstituted-cyclobut-2-en-1-ones under Suzuki Conditions and Their Synthetic Utility.

Autor: Alcaide B; Grupo de Lactamas y Heterociclos Bioactivos, Unidad Asociada al CSIC, Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, 28040, Madrid, Spain., Almendros P; Instituto de Química Orgánica General, IQOG, Consejo Superior de Investigaciones Científicas, CSIC, Juan de la Cierva 3, 28006, Madrid, Spain., Lázaro-Milla C; Grupo de Lactamas y Heterociclos Bioactivos, Unidad Asociada al CSIC, Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, 28040, Madrid, Spain.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2019 Jun 04; Vol. 25 (31), pp. 7547-7552. Date of Electronic Publication: 2019 Apr 18.
DOI: 10.1002/chem.201900690
Abstrakt: A regioselective synthesis of general applicability has been designed for the one-pot preparation of 2,3-disubstituted-cyclobutenones from iodoalkynes through cyclobutenylation, Suzuki CC coupling, and ketone formation. This one-pot methodology has been applied to the selective synthesis of an orally active cyclooxygenase II inhibitor. Furthermore, the obtained cyclobut-2-en-1-ones were used as synthons in several transformations, such as, the preparation of β-lactams, phthalazines, cyclohexa-2,5-dien-1-ones, and cyclopent-3-en-1-ones.
(© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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