3,6-Dipyridyl-1,2,4,5-tetrazines have been successfully synthesized for the 2, 3, and 4 substituted cyanopyridines with and without a sulfur catalyst. Inverse demand Diels alder has been carried out with these tetrazines using di-substituted, tri-substituted, and tetra-substituted alkenes as dieneophiles to yield 3,6-dipyridyl-1,2,4,5-pyridizines and 3,6-dipyridyl-1,4-dihydro-pyrizidines. Two and 4 substituted pyridyl groups on tetrazine acted as electon withdrawing groups, which accelerated the Diels alder reaction, while 3 substituted pyridyl groups acted as an electon donating groups, which retarded the Diels alder reaction. GCMS analysis has shown both formation of 3,6-dipyridyl-1,4-dihyropyrizidine and oxidized product 3,6-pyridyl pyrizidine for cyclohexene derivative. An aluminum trichloride catalyst has proven to be useful in Diels Alder involving the more substituted alkenes limonene and 2,3-dimethyl-2-butene.

Preparation and reactions of tetrazines and investigation of mechanism

247th National Meeting (2014)

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