Synthesis and chemical reactivity of the novel 3-chloro-3-(4-chlorocoumarin-3-yl)prop-2-enal
Ibrahim, Magdy; Nasser M. El-Gohary; El-kazak, Azza; Al-Shimaa Badran;
Abstract
Vilsmeier-Haack formylation of 3-acetyl-4-hydroxycoumarin (1) afforded the unexpected 3-chloro-3-(4-chlorocoumarin-3-yl)prop-2-enal (3). Compound 3 reacted with p-toluidine and benzylamine producing Schiff base 4 and enamine 6, respectively. Treatment of compound 3 with hydrazine hydrate produced bis-coumarin 15 which upon treating with hydrazine hydrate afforded bis chromeno[4,3-c]pyrazole derivative 16. Compound 3 reacted with cyanoacetohydrazide under different conditions. Condensation of compound 3 with some heterocyclic amines and 1,2-N,N-binucleophiles was studied. Structures of the new synthesized products were deduced on the basis of their analytical and spectral data.
Other data
| Title | Synthesis and chemical reactivity of the novel 3-chloro-3-(4-chlorocoumarin-3-yl)prop-2-enal | Authors | Ibrahim, Magdy ; Nasser M. El-Gohary; El-kazak, Azza ; Al-Shimaa Badran | Keywords | coumarins | Issue Date | Jul-2019 | Publisher | Elsiever | Journal | Tetrahedron | Volume | 75 | Issue | 3923 | Start page | 3932 | End page | 3932 | DOI | 10.1016/j.tet.2019.06.013 |
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