title: Reactions of Hexadehydro-Diels-Alder (HDDA)-Derived Benzynes with Thioamides: Synthesis of Dihydrobenzothiazino-Heterocyclics.
abstract: Reaction of thioamides (e.g., II) with benzynes generated by the hexadehydro-Diels-Alder (HDDA) cycloisomerization (e.g., I) produces dihydrobenzothiazines (e.g., III). It is postulated that the reaction proceeds via benzothietene (cf. IV) and o-thiolatoaryliminium (cf. V) intermediates and that the latter undergoes intramolecular 1,3-hydrogen atom migration to produce the penultimate isomeric iminium zwitterions VI.
authors.affiliation: Department of Chemistry, 207 Pleasant Street SE, University of Minnesota , Minneapolis, Minnesota 55455, United States.
authors.forename: Vignesh
authors.initials: V
authors.lastname: Palani
authors.affiliation: Department of Chemistry, 207 Pleasant Street SE, University of Minnesota , Minneapolis, Minnesota 55455, United States.
authors.forename: Junhua
authors.initials: J
authors.lastname: Chen
authors.affiliation: Department of Chemistry, 207 Pleasant Street SE, University of Minnesota , Minneapolis, Minnesota 55455, United States.
authors.forename: Thomas R
authors.identifier: 0000-0001-9318-1477
authors.initials: TR
authors.lastname: Hoye
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D061565:Cycloaddition Reaction; D003681:Dehydration; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013843:Thiazines / Q000138:chemical synthesis* / Q000737:chemistry; D013854:Thioamides / Q000737:chemistry*
chemical_list: D001555:Benzene Derivatives; D006571:Heterocyclic Compounds; D013843:Thiazines; D013854:Thioamides; C524146:benzyne