Abstract
Heterocyclic dienamines III. A re‐examination of the reaction of Fischer's base on tetracyanoethyleneDepending on the order of addition, Fischer's base 5 (1,3,3‐trimethyl‐2‐methylidene‐indoline) reacts 1:1 with tetracyanoethylene to give either the tricyanovinylation product 6 or the spiro compound 7. A skeletal rearrangement of a zwitterionic intermediate can explain the formation of the spiro compound. The latter undergoes a thermal isomerization yielding by ring expansion the tetrahydroquinoléine 8. On reaction with LiAlH4 or CH3ONa 7 and 8 lead both to triazatetracycles. All structures are assigned on the basis of spectral data.
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