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- W2002898532 abstract "A new reaction of 2-n-alkanoyl-1,2-dihydroisoquinaldonitriles 1 (isoquinoline Reissert compounds) has been discovered. As previously reported reaction of the conjugate bases of Reissert compounds with alkyl halides yields the corresponding 1-alkyl derivatives 2. However, compounds 2, R = n-alkyl, with only a catalytic amount of bases form the enolate ion, which attacks the neighboring nitrile functionality to produce directly in the same reaction vessel excellent yields of benzopyrrocoline derivatives 5-10. The nmr spectrum reveals a solvent dependent tautomeric equilibrium between ketoeneamine (a) and ketoimine (b) forms. Unlike compounds 2 the double bonds of the pyridine ring of compounds 7 and 8 were readily reduced with hydrogen. Thus, n-alkanoyl Reissert compounds afford a convenient route to the corresponding benzopyrroco-lines." @default.
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- W2002898532 date "1989-03-01" @default.
- W2002898532 modified "2023-09-23" @default.
- W2002898532 title "Novel tricyclic heterocycles (benzopyrrocolines) arisingviacarbanion attack on a nitrile function" @default.
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- W2002898532 doi "https://doi.org/10.1002/jhet.5570260217" @default.
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