Free accessResearch articleFirst published online 2001-8
Pyrrole studies,Part 48. 1 13 C NMR characterisation of imines and related compounds derived from pyrrole-2-carboxaldehydes and pyrrole-2,5-dicarboxaldehydes
In contrast with the imines formed from monoaminoalkanes and α,ω -diaminoalkanes with pyrrole-3,4-dicarboxaldehydes, which exist in a tautomeric 3H-pyrrole form, pyrrole-2-carboxaldehydes and -2,5-dicarboxaldehydes react with amines to produce 1H-pyrrolyl-methylenimines. Pyrrole-2,5-dicarboxaldehydes with 1,2-diamino-ethane and with 1,3-diaminopropane yield symmetrical macrocyclic systems, contrary to earlier reports.
Part 47. JonesR. A., Quintanilla-LópezG., TaheriS. A. N., HaniaM. M., ÖztürkO., and ZuilhofH., ARKIVOC, 2000, 1, 382. (Paper 0044).
2.
TaheriS.A. N., JonesR. A., BadeshaS. S., and HaniaM. M., Tetrahedron, 1989, 45, 7717.
3.
AdamsH., BaileyN. A., FentonD. E., MossS., Rodriguez de BarbarinC. O., and JonesG., J. Chem. Soc., Dalton Trans., 1987, 219.
4.
KiraM.A., Bruckner-WilhelmsA., RuffF., and BorsyJ., Acta Chim. Acad. Sci. Hung., 1968, 56, 189 (the dimeric product was incorrectly assigned the monomeric azafulvene structure).
5.
see, e.g., WatanabeM., KobayahiT., KajigaeshiS., and KanemasaS., Chem. Lett., 1975, 607; S. Mori, M. Watanabe, S. Kajigaeshi and S. Kumemasa, Heterocycles, 1976, 4, 957.
