Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 17, Pages 9707-9717Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01210
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- Russian Scientific Foundation [14-50-00069]
- Russian Science Foundation [14-50-00069] Funding Source: Russian Science Foundation
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The hydrolytic imidazoline ring expansion (HIRE) methodology was extended to readily available tetracyclic [1,4]thiazepines as well as sulfoxide and sulfone analogs thereof. The reactions resulted in the facile formation of a rare medium-sized [1,4,7]thiazecine ring system that has an emerging utility in bioactive compound design. Comparing the HIRE rates for representative compounds in the three groups of substrates allowed drawing some generalizations about the substituent effects on the course of the reaction.
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