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 language | English (US) |
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Pages (from-to) | 6312-6315 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 18 |
Issue number | 24 |
DOIs | |
State | Published - 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.