title: Powerful approach to heterocyclic skeletal diversity by sequential three-component reaction of amines, isothiocyanates, and 1,2-diaza-1,3-dienes.
abstract: By highly efficient, one-pot, three-component reactions, combining one set of 1,2-diaza-1,3-dienes (DDs), primary amines, and isothiocyanates in a different sequential order of addition, heterocyclic skeletal diversity can be achieved. The key feature discriminating the different heterocyclic core formation is the availability of the N or S heteronucleophile to give the first Michael addition step affording regioselective substituted 2-thiohydantoins or 2-iminothiazolidinones. The hydrazone or enehydrazino side chain at the 5-position of both heterocycles represents a valuable functionality to reach novel 5-hydroxyethylidene derivatives difficult to obtain by other methods.
authors.affiliation: Dipartimento SteVa, Sezione COSON, Università degli Studi di Urbino Carlo Bo, Via I Maggetti 24, 61029 Urbino, Italy.
authors.forename: Orazio A
authors.initials: OA
authors.lastname: Attanasi
authors.forename: Silvia
authors.initials: S
authors.lastname: Bartoccini
authors.forename: Gianfranco
authors.initials: G
authors.lastname: Favi
authors.forename: Gianluca
authors.initials: G
authors.lastname: Giorgi
authors.forename: Francesca Romana
authors.initials: FR
authors.lastname: Perrulli
authors.forename: Stefania
authors.initials: S
authors.lastname: Santeusanio
mesh_terms: D000588:Amines / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006827:Hydantoins / Q000737:chemistry; D017879:Isothiocyanates / Q000737:chemistry*; D015394:Molecular Structure; D011090:Polyenes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000588:Amines; D006571:Heterocyclic Compounds; D006827:Hydantoins; D017879:Isothiocyanates; D011090:Polyenes