Azomethine Chemistry. IV. Chemistry of Fused Thiazolidines^1,2

Synthesis of tricyclic isoindoles and thiazolo[3,2-c][1,3]benzoxazines

“…However, they were obtained as racemic mixtures. 4,6,7 Some 5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindoles substituted at C-9 with aryl and heteroaromatic groups have also been prepared as racemic mixtures although the separation of both enantiomers can be achieved by chromatography on cellulose triacetate. 5b…”

Exploiting azafulvenium methides chemistry

“…6,7,8 Compound 14a is also reported to react as an electrophile with hydrazines 9 and with primary amines, 10 giving hydrazones and imines of methyl pyruvate as products. The diester 14a reacts with DDQ to give a single product in high yield, a 1:1 adduct of the diester and DDQ (15), which structure was established by X-ray crystallography. Reaction of the diester 14a with methyl vinyl ketone gives the tetrahydropyridine 16 in moderate yield.…”

Highly diastereoselective synthesis of 2,3-dihydro-9bH- thiazolo[2,3-a]isoindolin-5-ones

“…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). Chiral compounds of this type are of interest as non-nucleosidic reverse transcriptase inhibitors.…”