Reactions of Hexadehydro-Diels-Alder (HDDA)-Derived Benzynes with Thioamides: Synthesis of Dihydrobenzothiazino-Heterocyclics

Vignesh Palani, Junhua Chen, Thomas R. Hoye

Research output: Contribution to journalLetter

15 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)6312-6315
Number of pages4
JournalOrganic Letters
Volume18
Issue number24
DOIs
StatePublished - Dec 16 2016

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