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Rare Medium-Sized Rings Prepared via Hydrolytic Imidazoline Ring Expansion (HIRE). 2018

Angelina Osipyan, and Alexander Sapegin, and Alexander S Novikov, and Mikhail Krasavin
Saint Petersburg State University , Saint Petersburg 199034 , Russian Federation.

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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