ChemInform Abstract: DIE SYNTH. VON 2‐(1‐NAPHTHYL)‐CUMARINO‐GAMMA‐PYRONEN

Thakar, K. A.; Manjaramkar, N. R.

doi:10.1002/chin.197141325

Chemischer Informationsdienst. Organische Chemie

1971

DOI: 10.1002/chin.197141325

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ChemInform Abstract: DIE SYNTH. VON 2‐(1‐NAPHTHYL)‐CUMARINO‐GAMMA‐PYRONEN

K. A. Thakar¹,

N. R. Manjaramkar²

Abstract: Die Hydroxyacetylcumarine (I) reagieren mit 1‐Naphthoesäurechlorid (II) in Pyridin zu den Naphthoyloxyverbindungen (III), die sich in einer Lösung von Kaliumhydroxid in Pyridin zu den Propandionen (IV) umlagem.

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Cited by 7 publications

(11 citation statements)

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“…The IR spectra of α-pyrono[2,3-f]chromones 6 show a strong band for the C=O stretching vibrations of the chromone carbonyl group, which is also characteristic for imines 5 as well as an additional strong band for the lactone carbonyl at 1720-1730 cm -1 , which corresponds to previous results [2,11,13]. The 1 H NMR spectra of diones 6 taken in CF 3 CO 2 D show the same set of characteristic signals for the protons of the chromone, triazole, and azaheterocyclic parts of the molecular as for imino derivatives 5 but the singlets of the protons at lowest field H-10 are shifted downfield by 0.2-0.3 ppm.…”

supporting

confidence: 78%

“…2-Aryl, 3-aryl, and 2-hetaryl derivatives of this system have bactericidal activity [1,2]. Methyl derivatives have been proposed as photo reagents for DNA [3].…”

mentioning

confidence: 99%

“…Derivatives with hetaryl groups at C-2 were obtained by the former approach: by the condensation of o-hydroxyacetylcoumarins with hetaroyl chlorides and subsequent rearrangement and cyclization [2,5]. Derivatives with hetaryl substituents at C-9 were obtained in our laboratory using the second approach by the reaction of 8-formyl-7-hydroxyisoflavones with hetarylacetonitriles [13].…”

mentioning

confidence: 99%

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Synthesis of 9-azolyl-3-(4-phenyl-4h-1,2,4-triazol-3-yl)-4h,8h-pyrano-[2,3-f]chromene-4,8-diones

Shokol

Лозинский

Туров

et al. 2009

Chem Heterocycl Comp

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The pyrano[2,3-f]chromene-4,8-dione system contains fragments of coumarin and chromone, both pharmacophoric molecules. 2-Aryl, 3-aryl, and 2-hetaryl derivatives of this system have bactericidal activity [1,2]. Methyl derivatives have been proposed as photo reagents for DNA [3].The pyrano[2,3-f]chromene-4,8-dione system may be obtained starting from both coumarins by completion of the γ-pyrone ring [1, 2, 4-6] and from chromones by annelation of the α-pyrone ring [1, 3, 7-13]. Derivatives with hetaryl groups at C-2 were obtained by the former approach: by the condensation of o-hydroxyacetylcoumarins with hetaroyl chlorides and subsequent rearrangement and cyclization [2,5]. Derivatives with hetaryl substituents at C-9 were obtained in our laboratory using the second approach by the reaction of 8-formyl-7-hydroxyisoflavones with hetarylacetonitriles [13]. 3-Hetaryl derivatives of this system have not yet been reported.In order to extend the range of heterocyclic derivatives of pyrano[2,3-f]chromene-4,8-dione we synthesized products containing azaheterocyclic substituents at C-3 and C-9.We used 6-ethyl-8-formyl-7-hydroxy-3-(4-phenyl-4H-1,2,4-triazol-3-yl)chromone (1) [14], which already has a heterocycle at C-3, as the starting compound. Chromone 1 was obtained by two methods: 1) formylation of 6-ethyl-7-hydroxy-3-(4-phenyl-4H-1,2,4-triazol-3-yl)chromone (2) using the Duff reaction and 2) heating the corresponding 8-diethylaminomethyl derivative 3 [15] in acetic acid at reflux in the presence of hexamethylenetetramine.The 1 H NMR spectrum of chromone 1 in DMSO-d 6 shows a singlet for the formyl proton at 10.54 ppm but lacks signals characteristic for the starting chromone 2 (6.91 ppm for H-8) and chromone 3 (Et 2 NCH 2 group signals). The signal for the 7-OH group is shifted downfield by 2 ppm as a consequence of formation of an

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supporting

confidence: 78%

“…2-Aryl, 3-aryl, and 2-hetaryl derivatives of this system have bactericidal activity [1,2]. Methyl derivatives have been proposed as photo reagents for DNA [3].…”

mentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis of 9-azolyl-3-(4-phenyl-4h-1,2,4-triazol-3-yl)-4h,8h-pyrano-[2,3-f]chromene-4,8-diones

Shokol

Лозинский

Туров

et al. 2009

Chem Heterocycl Comp

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“…The synthesis of compounds similar to angular α-pyrono [2,3-f]chromones is promising because they are active against S. aureus and E. coli [21,22]. Derivatives of this system were synthesized previously starting with 7-hydroxy-8-formylchromones using the Perkin [11,23,24] and Knoevenagel [24,25] reactions.…”

mentioning

confidence: 99%

“…The furo [2,3-h]chromone system is the basis of naturally occurring elliptone (20) [9,10] and caraniine (21) [12,13]. The α-pyrono [2,3-f]chromone core is found in clausenidin (22) [16,17], calomelanol D (23) [18], and schumanniophytine (24) [19,20].…”

mentioning

confidence: 99%

7-Hydroxy-3-phenoxy-8-formylchromones, analogs of natural flavonoids

et al. 2009

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UDC 547.814.5 7-Hydroxy-3-phenoxy-8-formylchromones were synthesized using the Duff reaction and were reacted with 2,4-dinitrophenylhydrazine to produce hydrazones and with an excess of hydrazine hydrate to produce the pyrazole recyclization products. Derivatives of α-pyrono[2,3-f]chromones were synthesized using the Knoevenagel condensation with 2-azahetarylacetonitriles and the Perkin reaction.Few 7-hydroxy-8-formylchromones (isounonal 1) and their partially hydrogenated derivatives, lavinal (2), and 4,7-dihydroxy-6-methyl-5-methoxy-8-formylflavan (3) have been discovered within the broad class of natural flavonoids. The first two occur together in plants of the family Annonaceae [1-6] such as Dasymaschalon rostratum [1], Desmos chinensis Lour [2], Desmos cochinchinensis [3], and Unona lawii Hook. f. & Thoms [4]. The last is found in roots of Desmos cochinchinensis [3]. A mixture of all three flavonoids isolated from D. cochinchinensis [3] exhibited antimalarial activity whereas lavinal itself was viewed as a potential AIDS agent [7]. Phenoxychromones are also found in nature [8]. This enabled us to combine these two classes into one in order to study properties different from those of each class individually but characteristic of the system as a whole.The classical method for synthesizing 7-hydroxy-8-formylchromones is the Duff reaction [9-15]. Starting 7-hydroxy-3-phenoxy-8-formylchromones 4-10 were synthesized using the Duff reaction by heating chromones 11-17 with urotropine in acetic acid with subsequent work up of the reaction mixture by HCl solution. PMR spectra of these compounds in DMSO-d 6 showed a singlet for the formyl group near 10.5 ppm and a broad singlet for the hydroxyl proton that was shifted to weak field relative to the resonance of the hydroxyl in the starting chromone by 1.6-1.7 ppm as a result of the formation of an intramolecular H-bond.The presence of the formyl group was also confirmed by formation of the 2,4-dinitrophenylhydrazone 18 upon reaction of 8 with 2,4-dinitrophenylhydrazine. The PMR spectrum of 18 exhibited resonances for aromatic protons characteristic of starting chromone 8; 1H doublets for H-5′′ and H-6′′ at 8.39 and 7.89 ppm, respectively; and a singlet for H-3′′ of the 2,4-dinitrophenyl group at 8.90 ppm.The reaction of 8-formylchromone 6 with an excess of hydrazine hydrate did not stop at the formation of the hydrazone but led to recyclization of theγ-pyrone ring to form pyrazole 19. This was confirmed by a broad singlet typical of the pyrazole NH proton at 12.90 ppm, singlets for two hydroxyls at 11.78 and 12.07, and a 2H singlet at 6.69 for the hydrazone amino group in the PMR spectrum recorded in DMSO-d 6 .

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Furyl analogs of α-pyrono[2,3-f]isoflavones with an azole substituent in the α-pyrone nucleus

Shokol

Лозинский

Tkachuk

et al. 2010

Chem Heterocycl Comp

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The pyrano[2,3-f]chromene-4,8-dione system is the basis of the natural compounds clauzenidine [1,2] and calomelanol D [3,4]. It enters into the composition of the pyridylchromone alkaloid schumanniophytin, isolated from the roots and bark of Schumanniophyton magnificum and S. problematicum [5][6][7].It is known that α-pyrono[2,3-f]flavones and isoflavones display bactericidal activity [8]. The same activity is also found for 2-hetarylpyrano[2,3-f]chromene-4,8-diones, including furyl analogs of α-pyrono-[2,3-f]flavones [9], which arouses interest in heterocyclic derivatives of this system.As a continuation of our investigations in the area of heterocyclic analogs of isoflavones [10] and complex flavonoids [11,12], in the present work we have synthesized furyl analogs of α-pyrono-[2,3-f]isoflavones containing azole substituents in position 9 of the molecule.3-Furyl-7-hydroxychromones 1 and 2 were used as starting compounds, and were formylated with hexamethylenetetramine in acetic acid according to the Daff reaction. The formation of the corresponding 8-formyl-substituted products 3 and 4 (Table 1) was confirmed by the absence from the 1 H NMR spectra of these compounds, recorded in DMSO-d 6 , of the singlet of the H-8 proton at 6.79 ppm characteristic of the initial chromones 1 and 2 ( Table 2). The singlet of the formyl group proton was found at 10.48-10.52 ppm, and the signal of the OH group proton was displaced relative to the analogous signal of compounds 1 and 2 by almost 2 ppm towards low field, as the result of the formation of a chelated intramolecular hydrogen bond. Confirmation of the chelate structure of compounds 3 and 4 is their red-brown coloration with an alcoholic solution of iron(III) chloride and the presence of a broad band at 3080-3090 cm -1 in their IR spectra.

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ChemInform Abstract: DIE SYNTH. VON 2‐(1‐NAPHTHYL)‐CUMARINO‐GAMMA‐PYRONEN

Abstract: Die Hydroxyacetylcumarine (I) reagieren mit 1‐Naphthoesäurechlorid (II) in Pyridin zu den Naphthoyloxyverbindungen (III), die sich in einer Lösung von Kaliumhydroxid in Pyridin zu den Propandionen (IV) umlagem.

Cited by 7 publications

References 0 publications

Synthesis of 9-azolyl-3-(4-phenyl-4h-1,2,4-triazol-3-yl)-4h,8h-pyrano-[2,3-f]chromene-4,8-diones

Synthesis of 9-azolyl-3-(4-phenyl-4h-1,2,4-triazol-3-yl)-4h,8h-pyrano-[2,3-f]chromene-4,8-diones

7-Hydroxy-3-phenoxy-8-formylchromones, analogs of natural flavonoids

Furyl analogs of α-pyrono[2,3-f]isoflavones with an azole substituent in the α-pyrone nucleus

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