Abstract
Condensation of 2-acetyl benzoic acid with aminothiols proceeds with extremely high diastereoselectivity to produce the desired 2,3-dihydro-9bH-thiazolo[2,3-a]isoindolin-5-one products in good yield. The relative stereochemistry of the major diastereoisomer, formed exclusively when using non-racemic aminothiol substrates, has been determined for the first time by single crystal X-ray analysis.
Highlights
The chemistry of the isoindolinone ring system is currently an area of interest for many research groups due to the actual and potential biological activities of many derivatives.[1]
Due to our general interest in this area of heterocyclic chemistry, we turned our attention to the 2,3-dihydro-9bH-thiazolo[2,3-a]isoindolin-5-one ring system (4)
Equimolar amounts of 2-acylbenzoic acids and the corresponding-aminothiols were heated at reflux under Dean-Stark conditions in xylene solvent for 24 h (Scheme 1)
Summary
The chemistry of the isoindolinone ring system is currently an area of interest for many research groups due to the actual and potential biological activities of many derivatives.[1]. Present a highly diastereoselective synthesis of the 2,3-dihydro-9bH-thiazolo[2,3-a]isoindolin-5one ring system.
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