Base-promoted ring opening of 3-chlorooxindoles for the construction of 2-aminoarylthioates and their transformation to quinazolin-4(3H)-ones. (1st March 2018)

• Record Type: Journal Article
• Authors: Poudel, Tej Narayan; Khanal, Hari Datta; Lee, Yong Rok
• Is Part Of: New journal of chemistry. Volume 42:Number 6(2018)
• Page Start: 4735
• Page End: 4741
• Publication Date: 2018-03-01
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c8nj00195b
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : Cesium carbonate-promoted synthesis of diverse 2-aminoarylthioates via ring opening of 3-chlorooxindoles with thiols, and their synthetic applications is demonstrated. Abstract : An unprecedented methodology for the preparation of diverse S -alkyl 2-aminoarylthioates has been developed based on cesium carbonate-promoted direct ring opening of 3-chlorooxindoles with thiols. This novel protocol proceeds via cascade sulfenylation, aerial oxidation, C2–C3 bond cleavage, and decarboxylation. The resulting products from this transformation exhibit potential for application as fluorescent sensors for the detection of Fe 3+ ions. In addition, this methodology provides a concise pathway for the construction of a variety of biologically interesting quinazolin-4(3 H )-ones in good yields.