Abstract
2-Alkyloxazolines and 2-alkylthiazolines react with 2-halobenzoyl chlorides to form N-(2-halobenzoyl)-cyclic ketene- N, O-acetals and N-(2-halobenzoyl)-cyclic ketene- N, S-acetals in excellent yields, respectively. These ketene acetals readily undergo stereocontrolled aryl radical cyclizations to afford the central six-membered rings of substituted-2,3,10,10α-tetrahydrooxazolo[3,2- b]isoquinolin-5-ones and their 2,3,10,10α-tetrahydrothiazolo[3,2- b]isoquinolin-5-one analogs. The tertiary N, O- and N, S-radicals formed upon aryl radical reaction at the ketene- N,X(X=O, S)-acetal double bond appear to have reasonable stability. The stereoselectivity in hydrogen abstractions by these intermediate radicals from both Bu 3SnH and (Me 3Si) 3SiH was investigated. The N, S-heterocyclic fused ring products may have potential medical value.
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