title: Synthesis of Cyclic Azomethine Imines by Cycloaddition Reactions of N-Isocyanates and N-Isothiocyanates.
abstract: Various nitrogen-substituted iso(thio)cyanates engage in [3 + 2]-cycloaddition reactions to form azomethine imines containing triazolone, triazole-thione, and pyrazole-thione cores. First, iminoisothiocyanates are shown to undergo aminothiocarbonylation reactions with strained alkenes, and a comparison with recently reported reactions of iminoisocyanates highlights their reduced reactivity. In contrast, amino(thio)carbonylation reactions of imines with iminoisocyanates and iminoisothiocyanates proved more efficient, providing access to triazolone and triazole-thione cores. The dipole products can be converted to valuable heterocyclic cores through simple derivatization reactions.
authors.affiliation: Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa , 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada.
authors.forename: Amanda
authors.initials: A
authors.lastname: Bongers
authors.affiliation: Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa , 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada.
authors.forename: Indee
authors.initials: I
authors.lastname: Ranasinghe
authors.affiliation: Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa , 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada.
authors.forename: Philippe
authors.initials: P
authors.lastname: Lemire
authors.affiliation: Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa , 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada.
authors.forename: Alyssa
authors.initials: A
authors.lastname: Perozzo
authors.affiliation: Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa , 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada.
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Vincent-Rocan
authors.affiliation: Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa , 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada.
authors.forename: André M
authors.initials: AM
authors.lastname: Beauchemin