Convenient Access to 2, 3‐Disubstituted‐cyclobut‐2‐en‐1‐ones under Suzuki Conditions and Their Synthetic Utility. Issue 31 (18th April 2019)

• Record Type: Journal Article
• Authors: Alcaide, Benito; Almendros, Pedro; Lázaro‐Milla, Carlos
• Is Part Of: Chemistry. Volume 25:Issue 31(2019)
• Page Start: 7547
• Page End: 7552
• Publication Date: 2019-04-18
• Subjects: alkynes -- cyclization -- ketones -- small ring systems -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201900690
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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. Abstract : A regioselective one‐pot methodology for the preparation of 2, 3‐disubstituted‐cyclobut‐2‐en‐1‐ones from iodoalkynes through sequential bis(triflyl)cyclobutenylation and Suzuki reaction with concomitant ketone formation has been developed. In addition, the obtained cyclobutenones were used as useful synthons in several transformations, such as the preparation of a cyclooxygenase II inhibitor.