title: Synthesis of benzodiazepine beta-turn mimetics by an Ugi 4CC/Staudinger/aza-Wittig sequence. Solving the conformational behavior of the Ugi 4CC adducts.
abstract: 5-Oxobenzo[e][1,4]diazepine-3-carboxamides were synthesized by sequential Ugi reaction-Staudinger/aza-Wittig cyclization. The pseudopeptidic backbone of the new benzodiazepine derivatives superimposed well with type I, I', II, and II' beta-turn motifs. The intermediate Ugi adducts were characterized as two conformers of the enol form by the correlation between (1)H NMR spectra and X-ray diffraction structures of model compounds.
authors.affiliation: Departamento de Química, Facultad de Ciencias & Parque Científico Tecnológico, Universidad de Burgos, 09001 Burgos, Spain.
authors.forename: María
authors.initials: M
authors.lastname: Sañudo
authors.forename: María
authors.initials: M
authors.lastname: García-Valverde
authors.forename: Stefano
authors.initials: S
authors.lastname: Marcaccini
authors.forename: Jacinto J
authors.initials: JJ
authors.lastname: Delgado
authors.forename: Josefa
authors.initials: J
authors.lastname: Rojo
authors.forename: Tomás
authors.initials: T
authors.lastname: Torroba
mesh_terms: D001569:Benzodiazepines / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D018716:Molecular Mimicry; D015394:Molecular Structure
chemical_list: D001569:Benzodiazepines