Synthesis p. 636 - 640 (1988)
Update date:2022-08-03
Topics:
Dormagen, Walter
Rotscheidt, Klaus
Breitmaier, Eberhard
1-Alkoxy-1,3-alkadienes and 5-vinyl-3,4-dihydro-2H-pyran (prepared by Wittig carbonyl olefination of 3-alkoxyacroleins and 5-formyl-3,4-dihydro-2H-pyran) undergo <4+2> cycloaddition with (tosyloxyimino)malononitrile in tetrahydrofuran/water at room temperature to give 5-alkyl-2,2-dicyano-6-ethoxy-1-tosyloxy-1,2,3,6-tetrahydropyridines and 7,7-dicyano-8-tosyloxy-3,4,6,7,8,8a-hexahydro-2H-pyrano<2,3-b>pyridine.These compounds can be converted into 6-alkoxy-5-alkyl-2,2-dicyano-2,3-dihydropyridines and pyridine-2-carboxamides, respectively.
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(1988)
