title: An efficient synthesis of symmetric and unsymmetric bis-(β-aminoamides) via Ugi multicomponent reaction.
abstract: A library of symmetrical and unsymmetrical bis-(β-aminoamides) has been prepared starting from symmetrical secondary diamines by using a double Ugi four-component reaction. A sacrifical Mumm rearrangement, thanks to the use of 2-hydroxymethyl benzoic acid, is necessary to suppress the competing split-Ugi reaction, increasing the yield and simplifying the purification step. The scope, the reaction conditions, and the role of water in trapping the nitrilium intermediate are also discussed.
authors.affiliation: Dipartimento di Scienze del Farmaco, Università degli Studi del Piemonte Orientale A. Avogadro, Largo Donegani 2, 28100 Novara, Italy.
authors.forename: Fabio
authors.initials: F
authors.lastname: La Spisa
authors.forename: Alberto
authors.initials: A
authors.lastname: Feo
authors.forename: Riccardo
authors.initials: R
authors.lastname: Mossetti
authors.forename: Gian Cesare
authors.initials: GC
authors.lastname: Tron
mesh_terms: D000083:Acetanilides / Q000138:chemical synthesis / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003959:Diamines / Q000737:chemistry*; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis / Q000737:chemistry; D000069458:Ranolazine; D013237:Stereoisomerism
chemical_list: D000083:Acetanilides; D000577:Amides; D003959:Diamines; D010879:Piperazines; D000069458:Ranolazine