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.
Citations
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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
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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
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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
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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, 5-Chromonylidene-2-methylthio-hydantoin derivatives were obtained by condensation of 3-formylchromones with hydantoin.
Abstract: 5-Chromonylidene-hydantoin, 2-thiohydantoin derivatives 2a–g, 3a,b were prepared by condensation of 3-formylchromones 1a,b with hydantoin, 2-thiohydantoin derivatives. Compounds 2a,b undergo Mannich reaction with formaldehyde and morpholine to give the corresponding Mannich prouducts 5a,b respectively. Reaction of 2a,b with alkylhalides namely Methyl iodide, Phenacly bromide, and Chloroacetic acid afforded the corresponding compounds 6a,b, 7a,b, 9a,b and 10a,b respectively. Reaction of 5-Chromonylidene-2-methylthio-hydantoin 6a,b with secondry and primary amines such as morpholine, piprazine, anthranilic acid, and glycine afforded the Glycocyamidine derivatives 11a,b, 12a,b, 13a,b and 15a,b. On reacting 2a,b with dazoalkanes afforded 16a,b and 17a,b respectively.
9 citations
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TL;DR: On the other hand, this paper showed that on heating under reflux in dry MeOH, aliphatic nitrones 2a−d produce corresponding carboxylic acids 4 but aromatic nitrones 1a−D give aldehyde 1.
Abstract: On hydrolysis with 70% H2SO4, aliphatic nitrones 2a–d produce the corresponding carboxylic acids 4 but aromatic nitrones 2e, f give aldehyde 1. On heating under reflux in dry MeOH, 2a–d rearrange t...
9 citations
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TL;DR: In this article, a variety of aldehydes and ketones were obtained at room temperature using thiols or dithiols in aqueous hydrobromic acid.
Abstract: Thioacetalization of a variety of aldehydes and ketones was achieved in excellent yields at room temperature using thiols or dithiols in aqueous hydrobromic acid. Thioacetals were also prepared by transthioacetalization of oximes, hydrazones, acetals and ketals under similar conditions. The use of aqueous hydrochloric acid, hydrofluoric acid and hydriodic acid for this transformation was also explored.
9 citations
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TL;DR: In this paper, a variety of the title phosphonic derivatives were synthesized in high yields starting from commercially available aldehydes and complete NMR cheracterization is reported for all compounds, which are useful intermediates for the synthesis of the phosphorus analogs of natural enzymes or peptides.
Abstract: A variety of the title phosphonic derivatives were synthesized in high yields starting from commercially available aldehydes. Complete NMR cheracterization is reported for all compounds, which are useful intermediates for the synthesis of the phosphorus analogs of natural enzymes or peptides.
9 citations