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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TL;DR: In this paper, the C 2 C 3 π-bond of allenic esters and the 1,3-dipolar cycloadducts formed undergo a series of intramolecular reorganisations including an intramerolecular (4+2) cycloaddition, in situ, to yield novel functionalized benzo[ b ]indolizines ( 3a-c ), in good yields.
24 citations
TL;DR: In this article, a simple one-pot synthesis of 3-cyano-4-benzopyrones from 2-hydroxyacetophenones using mild conditions is reported.
23 citations
TL;DR: Lithium dialkynylcuprates, 1a-d, are easily generated and undergo conjugate additions to activated chromones giving 2-alkynylchroman-4-ones 4a–d, 13, 15c,d and 5, however, 1,4-additions to 3 proceed anomalously to give the eneynonitriles 6a–b and the bisbenzopyranopyridine 7.
22 citations
TL;DR: In this paper, the authors showed that cycloadducts of dienamines with electrophilic acetylenes always undergo further transformations, resulting in the formation of xanthenone and substituted fumarate.
Abstract: Dienamine 1 with N-phenylmaleimide and chromenone 14 as well as 15 produces, through initial [4 + 2]cycloaddition, xanthenones 10 and 18, respectively Initial Michael addition of 1 to chromenones 14 and 16, and dimethyl acetylenedicarboxylate (DMAD), triggers the formation of xanthenone 19, 4-azaxanthenone 26 and substituted fumarate 49, respectively Initial [2 + 2]cycloadducts of dienamines 1–3 with electrophilic acetylenes always undergo further transformations Thus, 1 with DMAD, dibenzoylacetylene and ethyl propiolate (EP) ultimately gives xanthenones 33, 34 and 37, respectively, the latter being admixed with flavone 43 Enamine 2, cyclisable to xanthenone 11, gives 33 and 35 with DMAD, and 37 and 44 with EP Reaction of 3 with DMAD affords 36 exclusively
22 citations