title: Diversity-oriented heterocyclic synthesis using divergent reactivity of N-substituted iso(thio)cyanates.
abstract: Carbon-substituted isocyanates and isothiocyanates are common building blocks in organic synthesis. In contrast, synthetic uses of N-substituted isocyanates and isothiocyanates are severely underdeveloped: few have been reported and their reactivity had not been compared. Herein, we compare the reactivity of blocked (masked) N-isocyanate and N-isothiocyanate precursors in cascade reactions. Divergent reactivity is observed with secondary propargylic and allylic systems, leading to new syntheses of imidazolones, thiazolidines, and a tool to form complex azomethine imines.
authors.affiliation: Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5, Canada. andre.beauchemin@uottawa.ca.
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, ON K1N 6N5, Canada. andre.beauchemin@uottawa.ca.
authors.forename: Joshua S
authors.initials: JS
authors.lastname: Derasp
authors.affiliation: Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5, Canada. andre.beauchemin@uottawa.ca.
authors.forename: André M
authors.initials: AM
authors.lastname: Beauchemin
mesh_terms: D000480:Alkynes / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D007093:Imidazoles / Q000138:chemical synthesis; D007097:Imines / Q000138:chemical synthesis; D017953:Isocyanates / Q000737:chemistry*; D017879:Isothiocyanates / Q000737:chemistry*; D011437:Propylamines / Q000737:chemistry; D053778:Thiazolidines / Q000138:chemical synthesis
chemical_list: D000480:Alkynes; D007093:Imidazoles; D007097:Imines; D017953:Isocyanates; D017879:Isothiocyanates; D011437:Propylamines; D053778:Thiazolidines