title: An efficient microwave-assisted synthesis of cotinine and iso-cotinine analogs from an Ugi-4CR approach.
abstract: A convenient base-mediated two-step synthesis of cotinine analogs and a one-pot base-free synthesis of iso-cotinine derivatives featuring an Ugi-4CR/cyclization protocol are reported. These approaches exploit the reactivity of the peptidyl position present in the Ugi adducts, allowing the facile construction of the γ-lactam core, as well as the introduction of a N-substituted methyl group into the analogs in a straightforward manner. A plausible mechanism for the cyclization step is discussed.
authors.affiliation: Departamento de Química Orgánica, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510, México, D.F., México. joseavm@unam.mx.
authors.forename: Luis A
authors.initials: LA
authors.lastname: Polindara-García
authors.forename: Dario
authors.initials: D
authors.lastname: Montesinos-Miguel
authors.forename: Alfredo
authors.initials: A
authors.lastname: Vazquez
mesh_terms: D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003367:Cotinine / Q000737:chemistry*; D003500:Cyclization; D007769:Lactams / Q000737:chemistry*; D008872:Microwaves; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007769:Lactams; D003367:Cotinine