Journal
ORGANIC LETTERS
Volume 18, Issue 24, Pages 6312-6315Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b03199
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Funding
- National Institutes of General Medical Sciences of the U.S. Department of Health and Human Services [GM65597]
- Gleysteen-Heisig fellowship
- NIH Shared Instrumentation Grant program [S10OD011952]
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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.
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