Abstract
Photolyses of the thiohydroximate ester derivatives 13 and 21 of the 4- (benzyl-seleno)-2-azetidinoines 7 and 20, afford the 1-aza-7-oxo-4-selenabicyclo- [3.2.0]heptane ring systems 14 and 21 in good to moderate yield in processes that presumably involve intramolecular homolytic substitution at selenium with expulsion of benzyl radical. Extension of this methodology to the preparation of derivatives 24 of 12,2a-dihydro-1H,8H-azeto[2,1-b][1,3]benzoselenazin-1-one (22) is also described.
Highlights
Free-radical homolytic substitution chemistry is rapidly gaining acceptance as a versatile synthetic method [1]
In an attempt to extend the variety of available β-lactamase inhibitors, we considered that substitution of the sulfur atom in the bicyclic core with selenium may provide an analogue (5) of sulbactam that preserves its shape and electronic properties, but which may differ in reactivity, and potency
We report that selenium analogues of β-lactam antibiotic nuclei are conveniently prepared by extension of our previously established radical methodologies
Summary
Free-radical homolytic substitution chemistry is rapidly gaining acceptance as a versatile synthetic method [1]. Selenium analogues of β-lactam antibiotics have been reported on previous occasions together with limited biological testing data [9,10]. In each report the yields of the target molecules are either poor, or the compounds prepared bear functionality that compromises biological activity.
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