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) |
|---|---|
| Pages (from-to) | 6312-6315 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 18 |
| Issue number | 24 |
| DOIs | |
| State | Published - Dec 16 2016 |
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Palani, V., Chen, J., & Hoye, T. R. (2016). Reactions of Hexadehydro-Diels-Alder (HDDA)-Derived Benzynes with Thioamides: Synthesis of Dihydrobenzothiazino-Heterocyclics. Organic Letters, 18(24), 6312-6315. https://doi.org/10.1021/acs.orglett.6b03199