Dichotomic Dearomatizations of Benzene vs Pyridine Rings of Sulfonyloxypyridine via (3 + 2) Cycloaddition.

J Org Chem

Normandie Univ; UNILEHAVRE, URCOM, EA 3221, 25 rue Philipe Lebon, F-76600 Le Havre Cedex, France.

Published: September 2023

Electron-poor arenesulfonyloxypyridines are selectively dearomatized whether on the pyridine or on the phenyl group through 1,3-dipolar cycloaddition (1,3-DC) involving non-stabilized azomethine ylides (AMY). Electronic effects of substituents on the aromatic rings allow to induce the regioselectivity of the transformation. Novel pyrrolidinic polycyclic heterocycles are thereby produced under mild acidic conditions at room temperature.

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http://dx.doi.org/10.1021/acs.joc.3c00901DOI Listing

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