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 journalLetterpeer-review

18 Scopus citations


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
Issue number24
StatePublished - Dec 16 2016

Bibliographical note

Funding Information:
Support for this research was provided by the National Institutes of General Medical Sciences of the U.S. Department of Health and Human Services (GM65597). V.P. appreciates support from a Gleysteen−Heisig fellowship for undergraduate students. Some of theNMRdata were obtained with an instrument acquired with funds from the NIH Shared Instrumentation Grant program (S10OD011952).

Publisher Copyright:
© 2016 American Chemical Society.


Dive into the research topics of 'Reactions of Hexadehydro-Diels-Alder (HDDA)-Derived Benzynes with Thioamides: Synthesis of Dihydrobenzothiazino-Heterocyclics'. Together they form a unique fingerprint.

Cite this