Nitrogen containing heterocycles constitute a unique class of comopounds having a wide variety of biological activities and are widely used as antibiotic and antibacterial agents.1 Substituted tetrazoles have not been so widely used for the production of pharmaceuticals. β-lactam antibiotics and optically active tetrazole-containing antifungal preparations of the azole type, such as TAK-456.2,3 are well-known. Some of tetrazoles derivatives can also be used in DNA assays.4 Dioxa-9-azabicyclo[3.2.2]non-3-ene and 1,4,5,6-tetrahydropyridine-3-carbaldehyde are also believed to possess useful biological activities. As an extension of our studies on epoxy-ynamides,5-6 we demonstrate herein transition metal-free cyclization of epoxy benzene sulfonamide and β-chloro-cinnamaldehyde to afford substituted tetrazoles, 2,6-dioxa-9-azabicyclo[3.2.2]non-3-ene and 1,4,5,6-tetrahydropyridine-3-carbaldehyde. Key products have been characterized by single crystal X-ray crystallography.

Ring-Expansion Reactions of Epoxy Ene-Amides: Access to Substituted Tetrazoles, Dioxa-9-azabicyclo[3.2.2]nonenes and Tetrahydropyridine-3-carbaldehydes

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27th CRSI National Symposium in Chemistry

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