Chemistry and application of 4-oxo-4H-1-benzopyran-3-carboxaldehyde
TL;DR: The chemistry and application of the title aldehyde and some simple derivatives thereof are reviewed in this paper, where the authors propose a simple derivative of the aldehydes, which they call simple aldeheeds.
About: This article is published in Journal of Heterocyclic Chemistry.The article was published on 2008-11-01. It has received 42 citations till now. The article focuses on the topics: Benzopyran.
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71 citations
TL;DR: In this article, the starting materials were prepared by the reaction of 4-hydroxycoumarin with trifluoroacetic anhydride and methyl 2-chloro-2-oxoacetate in the presence of trimethylsilylchloride.
38 citations
TL;DR: A new mode of three-component reactions between isocyanoacetates, amines and 3-formylchromones is presented, which enables an efficient synthesis of polysubstituted pyrroles.
36 citations
TL;DR: The first synthesis of 3-methoxalylchromone was described, where the reaction of the latter with electron-rich aminoheterocycles afforded a set of heteroannelated pyridines bearing a CO(2)Me substituent located at the α-position of the pyridine core.
Abstract: The first synthesis of 3-methoxalylchromone was described. The reaction of the latter with electron-rich aminoheterocycles afforded a set of heteroannelated pyridines bearing a CO2Me substituent located at the α-position of the pyridine core.
34 citations
TL;DR: This review will cover the literature on the chromone and pyrazole dual chemistry and their outcomes in the 21st century with a focus on the synthesis of chromone-pyrazole dyads.
Abstract: Chromones, six-membered oxygen heterocycles, and pyrazoles, five-membered two-adjacent-nitrogen-containing heterocycles, represent two important classes of biologically active compounds. Certain derivatives of these scaffolds play an important role in medicinal chemistry and have been extensively used as versatile building blocks in organic synthesis. In this context, we will discuss the most relevant advances on the chemistry that involves both chromone and pyrazole rings. The methods reviewed include the synthesis of chromone-pyrazole dyads, synthesis of chromone-pyrazole-fused compounds, and chromones as starting materials in the synthesis of 3(5)-(2-hydroxyaryl)pyrazoles, among others. This review will cover the literature on the chromone and pyrazole dual chemistry and their outcomes in the 21st century.
33 citations
Cites background from "Chemistry and application of 4-oxo-..."
...The reactivity of 3-formylchromone derivatives with a series of hydrazines has been studied in detail over the most recent years (for recent reviews see [103,104])....
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References
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TL;DR: In this paper, functionalized benzophenones were prepared by domino "Michael-retro-Michael-aldol" reactions of 1,3-bis-silyl enol ethers with 3-formylchromones.
29 citations
TL;DR: In this article, a series of pyrazole-4-carboxylic acid hydrazides, modified to obtain N-(4-pyrazoyl) hydrazones, and study the antibacterial properties of the products.
Abstract: Proceeding from the fact that some widely used antibacterial preparations (furacilin, furazolidone, ftivazide) contain hydrazone groups, we decided to synthesize a series of pyrazole-4-carboxylic acid hydrazides, modify these compounds so as to obtain N-(4-pyrazoyl)hydrazones, and study the antibacterial properties of the products. Hydrazides IIIa – IIIg were synthesized based on the previously described pyrazole-4-carboxylic chloroanhydrides (Ia – Ig) [1]. Treated with methanol in the presence of an organic base, compounds Ia – Ig converted with a quantitative yield into the corresponding methyl esters IIa – IIg. Interaction of these intermediates with hydrazine hydrate (on heating in ethanol) led to a high yield of hydrazides IIIa – IIIg. The yields and physicochemical characteristics of methyl esters IIa – IIg and hydrazides IIIa – IIIg are listed in Table 1.
29 citations
28 citations
TL;DR: 3,4-Dihydro-2H-pyran reacts with a variety of chromone Schiff bases 3 in the presence of indium and scandium triflates at ambient temperature and pressure to give the endo cycloadducts 4 regiospecifically in high yields as mentioned in this paper.
Abstract: 3,4-Dihydro-2H-pyran reacts with a variety of chromone Schiff’s bases 3 in the presence of indium and scandium triflates at ambient temperature and pressure to give the endo cycloadducts 4 regiospecifically in high yields.
27 citations
TL;DR: In this paper, the synthesis of 1-benzopyrano[3,4d]isoxazole-4-one has been studied using 3-(alkyl-/aryl-aminomethylene)chroman-2,4-dione depending upon the reaction medium.
27 citations