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, a nucleophilic reaction of 3-formylchromones with tertiary push-pull enamines in refluxing acetonitrile gave polyfunctionalized benzophenone derivatives as a result of a [3+3] annulation in moderate to good yields.
9 citations
TL;DR: In this article, new antifungal agents have been prepared through reaction of 4-oxo-4 H -chromene-3-carbaldehydes (1a, b ) with some active primary amines (2a - e ) and amides/thioamides (6a - d ) in different conditions.
Abstract: Some new antifungal agents have been prepared through reaction of 4-oxo-4 H -chromene-3-carbaldehydes ( 1a , b ) with some active primary amines ( 2a - e ) and amides/thioamides ( 6a - d ) in different conditions. Structures of the products were established on the basis of elemental analysis, IR, 1 H NMR, mass spectra and semi-empirical AM1-MO calculations.
8 citations
TL;DR: In this paper, the reaction of 3-amino-4 H -chromeno[3,4-d ]isoxazol-4-ones with acetic and trifluoroacetic anhydrides gave the corresponding acetyl derivatives, which were rearranged into 2amino 4 H-chromeno [3, 4-d ][1, 3]oxazool-4 -ones by heating in DMSO solution.
8 citations
TL;DR: In this article, a review of recent developments of chemistry of synthetic analogs of natural compounds, isoflavone and homoisoflavones, is presented, with a focus on the application of modern strategies of organic synthesis, namely green chemistry approaches, click reactions, domino reactions, etc.
Abstract: The review is focused on recent developments of chemistry of synthetic analogs of natural compounds, isoflavone and homoisoflavone. The possible synthetic strategies to access heterocyclic analogs of these compounds starting from readily available 3-formylchromone and its derivatives (3-cyanochromone, 2-amino-3-formylchromone) and products of its condensation with simplest C- and N-nucleophiles are discussed. The structural features of the reaction products that depend on the nature of the reaction medium, structure of the starting compounds, and reagent ratio are considered. Particular attention is given to the application of the modern strategies of organic synthesis, namely green chemistry approaches, click reactions, domino reactions, etc. Examples of compounds of this group most promising for clinical application due to wide and pronounced pharmacological effects are given.
8 citations
TL;DR: A survey of advances in Heterocyclic Chemistry can be found in this paper, which includes monographs and reviews published during the period 2008-2009 as well as some published earlier but omitted in Part X.
Abstract: The survey is a sequel to 10 already published in Advances in Heterocyclic Chemistry . It includes monographs and reviews published during the period 2008–2009 as well as some published earlier but omitted in Part X. Just as in Parts III–X, sources not only in English but also in Russian, Japanese, Chinese, and other languages are surveyed and classified. This feature of the survey should cause no problem because some of the sources are available in English translations and practically all others have informative English abstracts as well as quite understandable and useful schemes and lists of references. As before, carbohydrates are not covered. Such compounds are mentioned only in general cases (e.g. anomeric effect) as well as when carbohydrates serve as starting compounds for the synthesis of other heterocycles or they are present as fragments of a complex system including another heterocyclic moiety such as nucleosides.
7 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