title: Leuckart-Wallach Route Toward Isocyanides and Some Applications.
abstract: Isocyanide-based multicomponent reactions (IMCR) are among the most important chemical reactions to efficiently generate molecular diversity and have found widespread use in industry and academia. Generally, isocyanides are synthesized in 1-2 steps starting from primary amines. Here, we provide experimental detail on an alternative approach toward formamides and, thus, isocyanides via the Leuckart-Wallach reaction in an improved variation. The resulting >50 synthesized and characterized formamides are useful starting materials for IMCR, as well as other chemistries. The advantage of using the Leuckart-Wallach pathway to formamides and isocyanides is the lower price, on average, of the starting materials, as well as their differential and complementary structural diversity, as compared to the primary amine pathway.
authors.affiliation: Department of Drug Design, University of Gröningen , A. Deusinglaan 1, Gröningen 9700AV, The Netherlands.
authors.forename: Constantinos G
authors.initials: CG
authors.lastname: Neochoritis
authors.affiliation: Department of Drug Design, University of Gröningen , A. Deusinglaan 1, Gröningen 9700AV, The Netherlands.
authors.forename: Tryfon
authors.initials: T
authors.lastname: Zarganes-Tzitzikas
authors.affiliation: Department of Drug Design, University of Gröningen , A. Deusinglaan 1, Gröningen 9700AV, The Netherlands.
authors.forename: Silvia
authors.initials: S
authors.lastname: Stotani
authors.affiliation: Carmolex, Inc. , Pittsburgh, Pennsylvania 15219, United States.
authors.forename: Adrian
authors.initials: A
authors.lastname: Dömling
authors.affiliation: Institut für Anorganische Chemie, Technische Universität München , 80333 München, Germany.
authors.forename: Eberhardt
authors.initials: E
authors.lastname: Herdtweck
authors.affiliation: Carmolex, Inc. , Pittsburgh, Pennsylvania 15219, United States.
authors.forename: Kareem
authors.initials: K
authors.lastname: Khoury
authors.affiliation: Department of Drug Design, University of Gröningen , A. Deusinglaan 1, Gröningen 9700AV, The Netherlands.
authors.forename: Alexander
authors.initials: A
authors.lastname: Dömling
mesh_terms: D000588:Amines / Q000737:chemistry; D003365:Costs and Cost Analysis; D003486:Cyanides / Q000138:chemical synthesis*; D005559:Formamides / Q000138:chemical synthesis; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy
chemical_list: D000588:Amines; D003486:Cyanides; D005559:Formamides; D007202:Indicators and Reagents
keywords: IMCR; Leuckart−Wallach; Ugi; formamides; isocyanides