Synthesis and chemical reactivity of the novel 3-chloro-3-(4-chlorocoumarin-3-yl)prop-2-enal

被引：8

作者：

El-Kazak, Azza M. ^{[1
]}

El-Gohary, Nasser M. ^{[1
]}

Badran, Al-Shimaa ^{[1
]}

Ibrahim, Magdy A. ^{[1
]}

机构：

[1] Ain Shams Univ, Fac Educ, Dept Chem, Cairo 11711, Egypt

来源：

TETRAHEDRON | 2019年 / 75卷 / 29期

关键词：

Coumarin; Vilsmeier-Haack; Nucleophilic reaction; Cyclocondensation; Pyrazolylcoumarin; Chromenopyrazoles; COUMARIN-DITHIOCARBAMATE HYBRIDS; BIOLOGICAL EVALUATION; MOLECULAR DOCKING; FLUORESCENT-PROBE; DERIVATIVES; DESIGN; ANTICANCER; ANTIMYCOBACTERIAL; INHIBITORS; HYDRAZONE;

D O I：

10.1016/j.tet.2019.06.013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页码：3923 / 3932

页数：10

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