Tetrahedron p. 5277 - 5290 (1993)
Update date:2022-08-03
Topics:
Rocha Gonsalves, Antonio M. D'A.
Pinhoe Melo, Teresa M. V. D.
Gilchrist, Thomas L.
The Diels-Alder reaction of 1,2,4-triazines with cyclic vinyl ethers leads to a range of substituted pyridines with hydroxyalkyl and oxoalkyl side chains. With dihydrofuran the aromatization of the 1:1 adduct is inhibited by conformational factors and this allows 2:1 adducts to be isolated. Different regioselectivity is observed in the 2:1 adducts formed from ethyl 5-phenyl-1,2,4-triazine-3-carboxylate 1f and from ethyl 5,6-diphenyl-1,2,4-triazine-3-carboxylate 1b. An X-ray crystal structure of the 2:1 adduct 5 formed from 2,3-dihydrofuran and 1b is reported.
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