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Convenient Access to 2,3‐Disubstituted‐cyclobut‐2‐en‐1‐ones under Suzuki Conditions and Their Synthetic Utility
Author(s) -
Alcaide Benito,
Almendros Pedro,
LázaroMilla Carlos
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900690
Subject(s) - synthon , regioselectivity , suzuki reaction , chemistry , combinatorial chemistry , ketone , organic chemistry , catalysis , palladium
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.