Chromone studies. Part 15. Formation and condensation of Baylis–Hillman adducts in DABCO-catalysed reactions of chromone-3-carbaldehydes with acrylonitrile
Free accessResearch articleFirst published online April, 2004
Chromone studies. Part 15. Formation and condensation of Baylis–Hillman adducts in DABCO-catalysed reactions of chromone-3-carbaldehydes with acrylonitrile
1,4-Diazabicyclo[2.2.2]octane(DABCO)-catalysed reactions of selected chromone-3-carbaldehydes with acrylonitrile (or methyl vinyl ketone) have led to the formation of Baylis–Hillman adducts and, in some cases, novel polycyclic condensation derivatives; electron-impact and electrospray MS fragmentation patterns have been examined for selected products.
Part 14. KayeP. T., NchindaA. T., SabbaghL. V., and BacsaJ., J. Chem. Res.(S), 2003, 111; J. Chem. Res.(M), 2003, 0301.
2.
LandquistJ.K., in Comprehensive Heterocyclic Chemistry, Ed. Meth-CohnO., Pergamon Press, Oxford, 1984, Vol. 1, p. 151.
3.
CoxJ.S. G., BeachJ. E., BlairA. M. J. N., ClarkeA. J., KingJ., LeeT. B., LovedayD. E. E., MossG. F., OrrT. S. C., RitchieJ. T., and SheardP., Advan. Drug Res., 1970, 5, 115; F. Pataloni and F. Ruggieri, Eur. Respir. J., 1989, 2, 566.
4.
NoharaA., UmetaniT., and SannoY., Tetrahedron Lett., 1973, 1995; A. Nohara, T. Umetani and Y. Sanno, Tetrahedron, 1974, 30, 3553.
5.
SabbaghL.V., PhD thesis, Rhodes University, 2000.
6.
As determined by 1H NMR analysis of the crude reaction mixture.
7.
BasavaiahD., RaoA. J., and SatyanarayanaT., Chem. Rev., 2003, 103, 811.
8.
NchindaA.T., PhD thesis, Rhodes University, 2001.
9.
PayneD.J., Hueso-RodriguezJ. A., BoydH., ConchaN. O., JansonC. A., GilpinM., BatesonJ. H., CheeverC., NiconovichN. L., PearsonS., RittenhouseS., TewD., DiezE., PerezP., De la FuenteJ., ReesM., and Rivera-SagredoA., Antimicrobial Agents and Chemotherapy, 2002, 46, 1880. (Chem. Abstr., 2002, 137, 137439.)
10.
KumagaiK., and HosotaniN., Patent application: WO 2003-JP567 20030122. (Chem. Abstr., 2003, 139, 148558.)
11.
BrogdenP.J., GabbuttC. D., and HepworthJ. D., in Comprehensive Heterocyclic Chemistry, Eds. BoultonA.J., and McKillopA., Pergamon, Oxford, 1984, Vol. 3, p. 613.
12.
Prepared using 3-hydroxyquinuclidine, as described for compound 5a.
