Novel reactivity for π-conjugated triazenes is herein reported. This observed and unprecedented triazene reactivity gave access to oxidation and substitution reactions. These transformations include successful synthesis of aldehydes, ketones, ethers, and sulfides from readily available organic azides via π-conjugated triazene intermediates. Notably, the afforded adducts were obtained in good yields, at room temperature, and in the absence of added metal catalysts.
A variety of chalcone derivatives were synthesized via aldol condensation of diverse aldehydes with acyclic and cyclic ketones, under mild reaction conditions. Reaction yields of pure products fluctuated from 48 % to 81 %. An unusually wide range of substrates including quinolines, thiophenes, pyridines, and fluorinated compounds were synthesized for this study. Full characterization data, along with in vitro antimicrobial activity for all adducts, are herein reported. Whole cell growth inhibition assays against staphylococcus aureus, escherichia coli, klebsiella pneumonia, acinetobacter baumannii, pseudomonas aeruginosa, candida albicans and cryptococcus neoformans var. grubii were performed employing all synthesized compounds (3a-m).
Metal‐free, compatible and synchronized aryl–aryl cross‐coupling and amide bond formation reactions were accomplished in a single step using π‐conjugated triazenes as the versatile starting materials. This simple, mild, and direct photochemical approach afforded anilides in good to excellent yields (up to 99%). Interestingly, natural sunlight is also shown to provide effective delivery of amides at ambient temperature. The successful synthesis of an immunosuppressant and the commercial drug acetaminophen validates this methodology. More information can be found in the Full Paper by Enrique Barragan, Anurag Noonikara‐Poyil, and Alejandro Bugarin.
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