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Investigation of the Reaction between 3‐Benzisothiazolones, an Isoindole Isoster and Activated Acetylenes: Synthesis of Heterocyclic Backbones for Building Bioactive Molecules
Author(s) -
Incerti Matteo,
Vicini Paola
Publication year - 2015
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2197
Subject(s) - chemistry , isothiazole , isoindole , triphenylphosphine , acetylene , molecule , combinatorial chemistry , bicyclic molecule , ring (chemistry) , cascade reaction , tandem , stereochemistry , organic chemistry , medicinal chemistry , catalysis , materials science , composite material
Investigation of the reaction between benzo[ d ]isothiazol‐3‐one, 2‐aminobenzo[ d ]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 biologically active molecules. A one‐pot PPh 3 ‐promoted tandem reaction , with acetylene dicarboxylates and dibenzoylacetylene, afforded new tricyclic pyrazolo‐fused benzisothiazoles. The PPh 3 ‐promoted reaction between benzisothiazolones and methyl propiolate afforded 1,4‐benzothiazepine‐5‐one derivatives, via an isothiazole ring expansion . These studies are providing additional insights in benzisothiazolone chemistry and describe simple and original synthetic accesses to novel derivatives.