Synthesis of benzodiazepine beta-turn mimetics by an Ugi 4CC/Staudinger/aza-Wittig sequence. Solving the conformational behavior of the Ugi 4CC adducts.
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.
Sañudo
María
M
Departamento de Química, Facultad de Ciencias & Parque Científico Tecnológico, Universidad de Burgos, 09001 Burgos, Spain.
García-Valverde
María
M
Marcaccini
Stefano
S
Delgado
Jacinto J
JJ
Rojo
Josefa
J
Torroba
Tomás
T
D001569:Benzodiazepines / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D018716:Molecular Mimicry; D015394:Molecular Structure
D001569:Benzodiazepines