Dichotomic Dearomatizations of Benzene vs Pyridine Rings of Sulfonyloxypyridine via (3 + 2) Cycloaddition
Sami Ben Salah1, Mohamed Othman1, Morgane Sanselme2
1Normandie Univ; UNILEHAVRE, URCOM, EA 3221, 25 rue Philipe Lebon, F-76600 Le Havre Cedex, France.
Abstract:
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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