ChemInform Abstract: Synthesis and Cleavage Reactions of Benzothiazepinylchromone Derivatives.

Shanker, Medi; Reddy, R. B.; Mouli, G. V. P. C.; Reddy, Y. D.

doi:10.1002/chin.199008194

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“…The reaction between 3-(2-acylvinyl)chromones and hydrazine in glacial acetic acid gives derivatives XXXVI containing pyrazoline ring [98], while the reaction of similar ehromones with o-aminothiophenol and subsequent intramolecular cyclocondensation gives products XXXVII containing benzothioazepine residue [99]. In the same study [104] was also found that reaction of nitrilimines XLV with substituted acetylenes and ethylenes gives pyrazolylchromones XLVI and pyrazolinylchromones XLVII, respectively.…”

Section: Methods Of Synthesis Of 3-hetarylchromonesmentioning

confidence: 87%

Preparation and reactions of isoflavone heteroanalogs (a review)

Frasinyuk¹,

Khilya²

1999

Chem Heterocycl Compd

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Methods for preparation of 3-hetarylchromones, which are isoflavone heteroanalogs, and the reactions of these compounds with either preservation or opening of the pyrone ring are reviewedThe 4H-[1]-benzo-4-pyranone (chromone) system is the basis of the chemical structure of a large group of biologically active natural products known as flavonoids and isoflavonoids. Replacement of the aryl residue in isoflavonoids by hetaryl residue leads to compounds having a broad range of biological activity arising from the combination of chromone and heterocyclic residues in a single molecule. Thus, 3-hetarylchromones, which have been termed isoflavonoid heteroanalogs, display strong antiallergenic [I-12], anticholesterol [13, 14], hypolipedimic [15, 16], antimicrobial [17, 18], anti-inflammatory [19], fungicidal [18], and antiblastic activity [20, 21] and are central nervous system stimulators [19,[22][23][24][25]. METHODS OF SYNTHESIS OF 3-HETARYLCHROMONESTwo major approaches have been developed for the synthesis of hetarylchromones. The first approach involves construction of the chromone system from substituted {x-hetaryl-2-hydroxyacetophenones, often using reagents such as ethoxalyl chloride, orthoformic ester, and acid anhydrides. The second method entails addition of the heterocycle to the prepared chromone system.The two approaches are examined in detail. Methods for the preparation of some starting substituted a-hetarylacetophenones are also given in Section 1.1. Examples of the synthesis of chromones containing completely or partially hydrogenated heterocyclic substituents are given in Section 1.2 (in light of their potential ability for conversion into 3-hetarylchromones by means of aromatization). Preparation of 3-hetaryichromones by construction of the chromone systemThienyl derivatives I--III have been obtained by cyclization of a-(2-thienyl)-2,4,6-trihydroxyacetophenone using ethoxalyl chloride [26]:Taras Shevchenko Kiev University, 252033 Kiev, Ukraine.

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Section: Methods Of Synthesis Of 3-hetarylchromonesmentioning

confidence: 87%