Abstract
The Hantzsh reaction of 7-hydroxy-8-methoxy-2-oxo-2H-1-benzopyran-6-carboxaldehyde (1) with ethyl acetoacetate and ammonia yields the dihydropyridine derivative 2 together with the pyridine derivative 3 and the eight membred ring derivative 4. Reaction of 1 with ethyl cyanoacetate and malononitrile gives the iminodicoumarin derivatives 5 and 6 respectiely. The latter compound was reacted with butan-2-one and acetophenone to produce the Michael adduct 7a, b and the 2-aminopyridine derivatives 8a, b.
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References Cited
Brokke, M. M. and Christensen, B. E., Psoralene 1 reactions of Xanthotoxin.J. Org. Chem., 23, 589–593 (1958).
Desheesh, M. T., Khalifa, M. S. and Kadous, E. A., Field and Laboratory trials of certain anticoagulaant rodenticides, Meded, Fac.Landbouwwvet, Rijksuniv Gent, 52(B), 555–560 (1987).
Esmon, C. T., Vigano D’Angles, S., D’Angels, A. and Comp, C. P., Anticoagulation proteins c and s.Adv. Exp. Med. Biol., 214, 47–54 (1987).
Gawron, A. and Glowniak, K., Cytostatic of coumarinsin vitro.Planta Med. 53(6), 526–529 (1987).
Lednicer, D. and Mitscher, L. A. The Organic Chemistry of Drug Synthesis, Wiley, New York, 1980.
O’Callaghan, C. N., Synthesis of dialkyl 2-(2-hydroxyphenyl)-4,6-dimethyl-1,2-dihydropyridine-3,5-dicarboxylates and alkyl 2,4-dimethyl-5-oxo-5H[1] benzopyrano [4,3-b]-pyridine-3-carboxylate, Synthesis, May, 499–503 (1987).
Smith, G. F., Neubauer, B. L., Sundboom, J. L., Best, K. L., Goode, R. L. Tanzer, L. R., Merriman, R. L. Frank, J. D. and Herrmann, R. G., Correlation of thevivo anticoagulant, antithrombotic and antimetastatic efficacy of Warfarin in the rat.Throm. Res., 50(1), 163–174 (1988).
Svetlik, J., Turecek, F. and Hanus, V., The Hantzsh synthesis with salicylaldehyde Revised. On the formation of bridged tetrahydropyridine derivatives.J. Chem. Perkin Trans., 1, 562–566 (1987).
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El-Diwani, H.I. Synthesis of some pyridine and dihydropyridine derivatives from 7-hydroxy-8-methoxy-2-oxo-2H-1-benzopyran-6-carboxaldehyde. Arch. Pharm. Res. 18, 27–30 (1995). https://doi.org/10.1007/BF02976503
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DOI: https://doi.org/10.1007/BF02976503