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Bridged Bicyclic γ-Sultams by Intramolecular Flow Photochemical [2 + 2] Cycloaddition
Yevhen O Zaika1,2, Illia O Borodin1,3, Heorhii O Olekh1,3
1Enamine Ltd., 78 Winston Churchill St, Kyiv 02094, Ukraine.
Abstract:
An elegant synthetic approach to the construction of a novel saturated heterocycle─2-thia-3-azabicyclo[2.1.1]hexane 2,2-dioxide─was designed. The key step included intramolecular flow photochemical [2 + 2] cycloaddition of appropriately substituted dienes, which were in turn obtained from readily available starting materials on a multigram scale. Further synthetic transformations of the resulting bicyclic compounds enabled the preparation of numerous functionalized derivatives useful for early drug discovery programs as promising isosteres of pyrrolidine, pyrrolidone, and γ-sultams. These studies also demonstrated the tolerance of the title bicyclic system to typical organic chemistry reaction conditions.
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