Diénamines hétérocycliques. III. Réexamen de la réaction de la base de Fischer avec le tétracyanoéthylène
- 1 June 1977
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 60 (4) , 1312-1321
- https://doi.org/10.1002/hlca.19770600420
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.Keywords
This publication has 8 references indexed in Scilit:
- Dienamines heterocycliques—ITetrahedron, 1976
- Deuterium isotope effects on 13C chemical shifts in amino acids and dipeptidesJournal of Magnetic Resonance (1969), 1975
- Addition reactions of heterocyclic compounds. Part LXI. Reactions of electrophilic acetylenes with conjugated cyclic enaminesJournal of the Chemical Society, Perkin Transactions 1, 1975
- Synthesen mit Nitrilen, XXXV. Reaktionen von Tetracyanäthylen mit HeterocyclenEuropean Journal of Inorganic Chemistry, 1973
- Stabile 1,4‐Dipole aus Ketenacetalen und 1,1‐Äthylen‐dicarbonitrilenAngewandte Chemie, 1967
- Retrograde Michael Reaction in Additions of Active Methylene Compounds to Tetracyanoethylene1The Journal of Organic Chemistry, 1962
- Cyanocarbon Chemistry. XIX.1,2 Tetracyanocyclobutanes from Tetracyanoethylene and Electron-rich AlkenesJournal of the American Chemical Society, 1962
- The Synthesis of Carbazoles from 3-Vinylindoles with Tetracyanoethylene and Dimethyl AcetylenedicarboxylateJournal of the American Chemical Society, 1959