Intramolecular hydrogen bonding allows simple enaminones to structurally mimic the i, i + 4, and i + 7 residues of an α-helix

An intramolecularly hydrogen bonded enaminone scaffold was designed and synthesized in order to mimic the i, i + 4, and i + 7 residues of an α-helix. The resonance stabilized vinylogous amide group serves as an aromatic ring isostere and allows the positioning and angular projection of the R-groups in a manner similar to an α-helix.