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: This paper showed that 3-formyl chromone with hydroxylamine hydrochloride afforded the corresponding oxime 2 that was converted to nitrile 3 by using hippuric acid.
Abstract: Condensation of 3-formyl chromone 1 with hydroxylamine hydrochloride afforded the corresponding oxime 2 that was converted to nitrile 3. Refluxing of oxime 2 and/or nitrile 3 with aceturic or hippuric acid gave 16 and 17. Treatment of 1 with semicarbazide hydrochloride and thiosemicarbazide afforded the corresponding carbazones 5–6 that underwent cyclization with ethyl bromoacetate and/or chloroacetone yielding 7–8. Also 1 reacted with acyclic active methylene reagents, e.g. malononitrile, ethyl cyanoacetate, and ethyl acetoacetate to form compounds 11, 12, and 13. Reaction of 1 with bifunctional reagents, e.g. benzil, o-phenylenediamine, o-aminophenol, and o-aminothiophenol yielding the corresponding imidazolyl bezopyranone and azepine derivatives 14–20. Condensation of 1 with acyclic or heterocyclic compounds containing active methylene group, e.g. hippuric acid forming the condensed products 21–27. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:20–27, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20048
37 citations
TL;DR: In this article, a range of fullerene-chromone dyads were prepared by 1,3-dipolar cycloaddition reactions of azomethine ylides to C60 and by cyclopropanation of C60 with flavonyl malonates.
36 citations
TL;DR: The reaction of 2-(N-methylanilino)-3-formylchromones with a number of bifunctional nucleophiles, involving substitution of N-methyl-lino moiety and/or condensations with 3-formedyl function have provided an easy access to a variety of potentially biologically active hetero-annelated chromones, novel macrocycles, and tetradentate ligands having intact chromone moiety as discussed by the authors.
36 citations
TL;DR: In this paper, the Vilsmeier-Haack reaction conditions were applied to bound o -hydroxyacetophenone (HO) under VILHAHAACK reaction conditions, yielding synthetic equivalents of 3-formylchromone (1 ) and chromone (13 ) respectively.
34 citations
TL;DR: In this paper, complete peri-, regio- and stereoselectivities in thermal reactions of C-(4oxo-4H[1]benzopyran-3-yl)-N-phenylnitrones with both electron-rich and electron-deficient olefins have been investigated.
32 citations