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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TL;DR: In this article, 3-Diaminomethylidene-chromane-2,4-diones were synthesized from 4-oxo-4H-chromene-3-carbaldehyde and hydroxylamine without isolation of intermediate products.
Abstract: 3-(Diaminomethylidene)chromane-2,4-diones were synthesized from 4-oxo-4H-chromene-3-carbaldehyde and hydroxylamine in the presence of sodium hydroxide without isolation of intermediate products. Reflux of 3-(diaminomethylidene)chromane-2,4-dione in acetic anhydride gives rise to their monoacetyl derivatives at one of the amino groups.
4 citations
01 Feb 2016
TL;DR: Highly functionalized pyridin-2(1H)-one derivatives were synthesized in high yields by a sequential multicomponent reaction involving the Michael addition of Meldrum's acid to 3-formylchromone, followed by the addition of an amine, intramolecular amidation and elimination of acetone.
Abstract: Highly functionalized pyridin-2(1H)-one derivatives were synthesized in high yields by a sequential multicomponent reaction. The mechanism involves the Michael addition of Meldrum's acid to 3-formylchromone, followed by the addition of an amine, intramolecular amidation and elimination of acetone. Depending on the temperature used, decarboxylation can occur. The mechanism of this reaction has been proposed based on the by-products obtained when the reaction was performed using poorly reactive amines. The versatility of this approach has been exemplified using various 3-formylchromones and amines. Analogues of Meldrum's acid were also tested, allowing the synthesis of pyridin-2(1H)-one derivatives with various substituents on the aromatic ring.
4 citations
TL;DR: In this article, a flexible approach to the synthesis of phenanthrene-like heterocycles through organocatalytic ANRORC reaction of electron-deficient 3-vinylchromones with cyanoacetamide was reported.
Abstract: We report a flexible approach to the synthesis of phenanthrene-like heterocycles through organocatalytic ANRORC (Addition of the Nucleophile, Ring Opening, and Ring Closure) reaction of electron-deficient 3-vinylchromones with cyanoacetamide. Addition of highly basic DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) or tetramethylguanidine (TMG) at 80 °C leads to chromeno[4,3-b]pyridines in good yields, whereas Et3 N at 20 °C made it possible to obtain the less accessible pyrano[3,2-c]chromenes and their 2-imines. The synthesis proceeds in mild conditions (EtOH, 20-80 °C), is versatile and applicable for a wide scope of reactants. The obtained compounds show bright fluorescence in the range 460-595 nm with high quantum yields (up to 0.84) in various solvents (MeCN, DMSO, EtOH, H2 O).
3 citations
TL;DR: Arylaminomethylidenechroman-2-carboxamide has been synthesized by a one-pot three component reaction among 3-formylchromone, aromatic amine, and cyclohexyl isocyanide as mentioned in this paper.
3 citations
TL;DR: Xanthoquinones, as a new class of quinone dyes comprising the xanthone and quinones subunits have been synthesized in this article , where an elusive aminofurochromone as an electron-rich diene was generated in situ from the corresponding chromone-3-carbaldehyde and alkyl or aryl isocyanide via a formal [4 + 1] cycloaddition reaction.
2 citations
References
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TL;DR: A highly efficient, mild, and simple protocol is presented for the oxidation of aldehydes to carboxylic acids utilizing Oxone as the sole oxidant.
412 citations
TL;DR: Quantitative structure-activity relationship (QSAR) analysis showed that, besides the essential pharmacophore (-NHCONHOH), hydrophobicity, molecular size/polarizability, and the presence of an oxygen-containing group at the ortho position (I) were important determinants for the antitumor activities.
Abstract: Thirty Schiff bases of hydroxysemicarbazide (Ar−CHNNHCONHOH) have been synthesized and tested against L1210 murine leukemia cells. The IC50 values were found to be in a range from 2.7 × 10-6 to 9.4 × 10-4 M. A total of 17 out of the 30 compounds had higher inhibitory activities than hydroxyurea (an anticancer drug currently used for the treatment of melanoma, leukemia, and ovarian cancer) against L1210 cells. Six compounds with IC50 values in micromolar range were 11- to 30-fold more potent than hydroxyurea (IC50 = 8.2 × 10-5 M). The partition coefficient (log P) and ionization constants (pKa) of a model compound [1-(3-trifluoromethylbenzylidene)-4-hydroxysemicarbazide, 1] were measured by the shake-flask method, and the measured log P was used to derive Hansch−Fujita π constant of −CHNNHCONHOH. On the basis of the newly derived π and those of other moieties, the partition coefficients (SlogP) of the other 29 compounds were calculated by the summation of π values. Quantitative structure−activity relations...
257 citations
TL;DR: By the application of the Vilsmeier-Haack reaction to various o-hydroxyacetophenone derivatives, 4-oxo-4H-1-benzopyran-3-carboxaldehydes were synthesized in one step as discussed by the authors.
175 citations
TL;DR: In this paper, the condensation reaction of 4-oxo-(4H)-1-benzopyran-3-carbaldehydes and of aromatic aldehydes with 3-methyl-1-phenylpyrazolin-5-4H-one were carried out in an ionic liquid, ethylammonium nitrate, at room temperature in shorter times with higher yields of 78−92 and 70−75%, respectively, than found using conventional procedures.
114 citations
TL;DR: The compounds displayed promising anticancer activity under these test systems and shall serve as useful 'leads' for further design.
88 citations