Synthesis of a Library of “Lead-Like” γ‑Lactams by a One Pot, Four-Component Reaction
journal contributionposted on 08.07.2013, 00:00 by Kevin S. Martin, Michael J. Di Maso, James C. Fettinger, Jared T. Shaw
The synthesis of a pilot scale library of 116 structurally diverse γ-lactams is reported. The library core structure emanates from a γ-lactam forming one-pot, four-component reaction of ammonium acetate, p-methoxythiophenol, p-methoxybenzaldehyde, and maleic anhydride. Structural diversity then arises from amide coupling, thioaryl cleavage, N-functionalization, and heterocycle forming reactions on this core structure. Computational analysis reveals that the library contains molecular properties and shape diversity suitable for drug lead and biological probe discovery.