Abstract
Dimethylacetylenedicarboxylate reacts with Fischer's base (1,3,3-trimethyl-2-methylene indoline) to give a zwitterionic intermediate which undergoes a Michael type addition in MeOH or cyclisation and ring opening in CHCl 3 to yield isomeric dienamines. Methyl propiolate, in addition to both the products observed previously, gives the ω-methoxycarboxylated Fischer's base in CHCl 3, whereas in CCl 4 a chlorinated dienamine is obtained. The solvent effect has been rationalised. Some dienamines react with tosylated oximes yielding azatrienes. The structures of the reaction products have been assigned on the basis of spectral data. A large difference of NMR chemical shift for the methyl groups bonded to the indoline ring has been observed depending upon the E and Z structure of the substituted Fischer's base.
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