Synthetic study demonstrates strain-release functionalization of vinyl-azabicyclobutanes into tetrasubstituted alkylidene-azetidines, suggesting their potential as broad-spectrum antibacterials.
A new class of azetidine-tethered allylic acetates was prepared via strain-release reactions of vinyl-ABB using acetic acid as nucleophile and used for Tsuji-Trost allylation. A broad range of primary and secondary alkylamines, sulfinates, active methylene compounds and azlactones were employed as nucleophiles to access tetrasubstituted alkylidene-azetidines in good yield. Also, in the absence of any nucleophile, acetate rearrangement was reported via the attack of the counter acetate anion from the less hindered site of the π-allyl-palladium species. Boc-deprotected tetrasubstituted alkylidene azetidine shows promising antibacterial activity against both Gram-positive and Gram-negative bacteria.
No takes yet. Share an insight, caveat, or question.
Hazra et al. (2026) studied this question.
Synapse has enriched 5 closely related papers on similar clinical questions. Consider them for comparative context: