A Novel Base-Catalyzed Carbon-Nitrogen Bond Fission in Some Heterocycles

Article abstract of DOI:10.1021/jo00304a025

Nitrogen heterocycles bearing a nonbasic nitrogen atom and other defined structural features as exemplified by 9,10-dimethoxy-3,4,6,7-tetrahydro-2H-pyrimido<6,1-a>isoquinoline-2,4-dione (1), 8-oxypseudopalmatine (22), 8-oxypseudoberberine (25), rutaecarpine (39), and related systems, on heating with excess sodium hydride in polar aprotic solvents, undergo a facile carbon-nitrogen bond cleavage reaction to give new nitrogen heterocycles with an arylvinyl group as one of the substituents.The nature, scope, postulated mechanism, and limitations of this novel carbon-nitrogen cleavage reaction are described.