title: Synthesis of heterocycles by formal cycloadditions of isocyanides.
abstract: Synthetic methodology for the synthesis of heterocycles is of continuous and high interest with applications in materials, catalysis, and medicines. Multicomponent reactions are suitable tools to efficiently generate chemically diverse sets of heterocycles with sufficient structural complexity. Especially isocyanides have proven to be particularly versatile building blocks in these one-pot processes. Due to their electronic structure, isocyanides are able to act sequentially or simultaneously as a nucleophile and an electrophile. Traditionally, isocyanides are therefore frequently used in multicomponent chemistry. In the recent literature, numerous reactions have been reported that involve formal cycloadditions of isocyanides with conjugated heterodienes. This Focus Review aims at mapping this reactivity and at providing insight into the relationship between the various reported reaction partners and the observed reactivity modes.
authors.affiliation: Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules, Medicines and Systems, VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands).
authors.forename: Art
authors.initials: A
authors.lastname: Kruithof
authors.forename: Eelco
authors.initials: E
authors.lastname: Ruijter
authors.forename: Romano V A
authors.initials: RV
authors.lastname: Orru
mesh_terms: D020650:Combinatorial Chemistry Techniques; D003486:Cyanides / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D003486:Cyanides; D006571:Heterocyclic Compounds
keywords: combinatorial chemistry; conjugated heterodienes; isocyanides; molecular orbitals; multicomponent reactions