1,2 and 1,4‐Dihydropyridine from 4‐Oxo‐4<i>H</i>‐chromen‐3‐carbaldehyd

Görlitzer, K.; Michels, K.

doi:10.1002/ardp.19883210918

Cited by 12 publications

(7 citation statements)

References 2 publications

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“…However, the reaction of enamines with 3-formylchromones is well documented [11,12]. There is no report on their reaction with the 3-cyano analogs so far.…”

Section: Resultsmentioning

confidence: 97%

Synthesis of new benzo[h]‐ and benzo[f]chromeno[2,3‐b]‐pyridine‐5‐ones

Abdel-Rahman

Girges

El-Ahl

et al. 2006

Heteroatom Chemistry

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“…However, the reaction of enamines with 3-formylchromones is well documented [11,12]. There is no report on their reaction with the 3-cyano analogs so far.…”

Section: Resultsmentioning

confidence: 97%

Synthesis of new benzo[h]‐ and benzo[f]chromeno[2,3‐b]‐pyridine‐5‐ones

Abdel-Rahman

Girges

El-Ahl

et al. 2006

Heteroatom Chemistry

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“…The Hantzsch reaction of 3-formylchromone with esters of 13-aminocrotonic acid in acetic acid gives a mixture of substituted 3-(1,2-dihydro-2-pyridyl)-(XXV) and 3-(1,4-dihydro-4-pyridyl)chromones (XXVI), which were separated chromatographically and dehydrogenated to give the corresponding 3-pyridylchromones XXVII and XXVIII [91 ].…”

Section: Methods Of Synthesis Of 3-hetarylchromonesmentioning

confidence: 99%

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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“…3-Chlorochromone or 3-bromochromone (12) (R = H, Me) when either heated neat or treated in MeCN containing K 2 CO 3 at room temperature with pyrrolidine (13) (n = 1, X = CH 2 ) gives 3-(1-pyrrolidinyl)chromone (16). Several other heterocyclic compounds are also bestowed with some biological activities.…”

Section: Introductionmentioning

confidence: 99%

“…represented by the general structure (16) and synthesised from the appropriate 3-chloro(or bromo)chromone and cyclic amine 6,7 are listed in catalysed Suzuki coupling with lithiated trimethyl pyridine-3-boronate in boiling PhMe -EtOH containing Na 2 CO 3 . 13 The dihydroxyacetophenone (31) (Het = 2-quinolyl), derived from resorcinol and quinolin-2-acetonitrile, cyclises with refluxing HC(OEt) 3 or Ac 2 O to give 32 (R = R 1 = H or R = Me, R 1 = Ac) in 80-86% yield.…”

Section: Introductionmentioning

confidence: 99%