Investigation of the Reaction between 3‐Benzisothiazolones, an Isoindole Isoster and Activated Acetylenes: Synthesis of Heterocyclic Backbones for Building Bioactive Molecules. (19th June 2014)

• Record Type: Journal Article
• Authors: Incerti, Matteo; Vicini, Paola
• Is Part Of: Journal of heterocyclic chemistry. Volume 52:Number 4(2015)
• Page Start: 1240
• Page End: 1244
• Publication Date: 2014-06-19
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.2197
• Languages: English
• ISSNs: 0022-152X

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>Investigation of the reaction between benzo[<italic>d</italic>]isothiazol‐3‐one, 2‐aminobenzo[<italic>d</italic>]isothiazol‐3‐one, its isoster 2‐aminoisoindolin‐1‐one, and activated acetylenes, in the presence of triphenylphosphine, led us to synthesize novel heterocyclic compounds that could be attractive for the building of <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">biologically active</named-content> molecules. A one‐pot PPh₃‐promoted <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">tandem reaction</named-content>, with acetylene dicarboxylates and dibenzoylacetylene, afforded new tricyclic pyrazolo‐fused benzisothiazoles. The PPh₃‐promoted reaction between benzisothiazolones and methyl propiolate afforded 1, 4‐benzothiazepine‐5‐one derivatives, via an isothiazole <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">ring expansion</named-content>. These studies are providing additional insights in benzisothiazolone chemistry and describe simple and original synthetic accesses to novel derivatives.</p> </abstract>