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 paper, a series of substituted azoles, azines, and azepines linked to the α-aminophosphonate moiety was achieved, based on ring opening and ring closure (RORC) of the chromone ring of diethyl chromonyl α-amino acid 1 via its reaction with nitrogen nucleophiles such as primary amines and 1,2-, 1,3-, and 1 4-bi-nucleophiles in ethanolic sodium ethoxide.
21 citations
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...[1,2] The 3-heteroaryl chromones possess The 18 th International Electronic Conference on Synthetic Organic Chemistry 1-30 November 2014...
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TL;DR: Chromone and chromone-3-carboxylic acid react with cyanoacetic acid hydrazide in the presence of NaOEt in boiling ethanol to form 6-(2-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridin-3(2H)-one (58-62% yields).
18 citations
TL;DR: While 2-(trifluoromethyl)chromones react with cyanoacetamides in the presence of sodium ethoxide to produce 6-(2-hydroxyaryl)-4-(trifi-ormethyl)-2-oxo-1,2-dihydropyridine-3-carbonitriles as discussed by the authors, their reactions with ethyl-cyanoacetate and diethyl malonate under the same conditions took an entirely different course and gave novel functionalized derivatives of 6H-benzo[c]chromen
15 citations
TL;DR: In this article, a selective synthesis of 2-hydroxy-4-4−hydroxybenzophenones or their 3−acylated counterparts through cascade reactions of 3-formylchromones with diversely substituted penta-3,4-dien-2-ones is presented.
Abstract: A selective synthesis of 2-hydroxy-4′-hydroxybenzophenones or their 3′-acylated counterparts through the cascade reactions of 3-formylchromones with diversely substituted penta-3,4-dien-2-ones is presented. Mechanistically, the formation of the title compounds involves either an unprecedented [4 + 2] annulation or a well defined [3 + 3] cyclization depending on the substitution patterns of the penta-3,4-dien-2-one substrates.
14 citations
TL;DR: The reaction of 3-cyanochromones with o-phenylenediamines gave 2-amino-3-[(2-aminophenyl)iminomethyl]-4H-chromen-4-ones.
14 citations
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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