SCOPUS 정보 검색 플랫폼

Volumn , Issue 20, 2007, Pages 3113-3116

A novel and efficient route for the synthesis of hydroxylated 2,3-diarylxanthones

(3) Santos, Clementina M M a,b Silva, Artur M S b Cavaleiro, José A S b

a INSTITUTO POLITÉCNICO DE BRAGANÇA (Portugal)

Author keywords

3 bromo 2 styryl chromones; Demethylation; Heck reaction; Hydroxylated diarylxanthones; Phenyltrimethylammonium tribromide

Indexed keywords

2 (4 HYDROXYPHENYL) 3 (3,4 DIHYDROXYPHENYL)XANTHONE; 2 (4 METHOXYPHENYL) 3 (3,4 DIMETHOXYPHENYL) 3,4 DIHYDROXANTHONE; 2 (4 METHOXYPHENYL) 3 (3,4 DIMETHOXYPHENYL)XANTHONE; 3 BROMO 2 STYRYLCHROMONE; 3 BROMO 3',4' DIMETHOXY 2 STYRYLCHROMONE; CHROMONE DERIVATIVE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; DEMETHYLATION; HECK REACTION; HYDROXYLATION; METHYLATION; NUCLEAR MAGNETIC RESONANCE; ONE POT SYNTHESIS; SUBSTITUTION REACTION; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 37749014302 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-990900 Document Type: Article

Times cited : (21)

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- Typical Experimental Procedure: Phenyltrimethylammonium tribromide (PTT; 2.1 g, 5.5 mmol) was added to a THF (60 mL) solution of the appropriate 5-aryl-3-hydroxy-1-(2-hydroxyphenyl)-2,4-pentadien-1-ones 4a-c (5 mmol, The reaction mixture was stirred and allowed to stand at r.t. for 12 h. After that period, the solution was poured into ice (50 g) and H2O (80 mL, stirred for 20 min and the yellow solid was removed by filtration. The residue was taken in CHCl3 (50 mL) and washed with H2O (3 x 50 mL, The organic layer was collected, the solvent was evaporated to dryness and the residue was purified by silica gel column chromatography using CH 2Cl2 as eluent. The solvent was evaporated and the residue was recrystallized from EtOH to give the 3-bromo-2-styrylchromones 5a-c in good yields 5a: 67, 5b: 53, 5c: 64
- 2 as eluent. The solvent was evaporated and the residue was recrystallized from EtOH to give the 3-bromo-2-styrylchromones 5a-c in good yields (5a: 67%; 5b: 53%; 5c: 64%).

31
- 37749039214
- Physical Data of 3-Bromo-3′,4′-dimethoxy-2-styryl-chromone (5c, mp 187-189°C 1H NMR (300.13 MHz, CDCl3, δ, 3.95 (s, 3 H, 4′-OMe, 3.98 (s, 3 H, 3′-OMe, 6.92 (d, J, 8.3 Hz, 1 H, H-5′, 7.14 (d, J, 2.0 Hz, 1 H, H-2′, 7.24 (dd, J, 2.0, 8.3 Hz, 1 H, H-6′, 7.33 (d, J, 15.8 Hz, 1 H, H-α, 7.41 (ddd, J, 0.8, 7.7, 7.8 Hz, 1 H, H-6, 7.53 (d, J, 7.9 Hz, 1 H, H-8, 7.66 (d, J, 15.8 Hz, 1 H, H-β, 7.70 (ddd, J, 1.6, 7.7, 7.9 Hz, 1 H, H-7, 8.23 (dd, J, 1.6, 7.8 Hz, 1 H, H-5, 13C NMR (75.47 MHz, CDCl 3, δ, 55.96, 55.99 (3′-OMe, 4′-OMe, 109.0 (C-3, 109.6 (C-2′, 111.1 (C-5′, 116.9 (C-α, 117.4 (C-8, 122.1 (C-10, 122.6 (C-6′, 125.3 (C-6, 126.4 (C-5, 127.9 (C-1′, 133.9 (C-7, 139.6 (C-β, 149.3 (C-3′, 151.2 (C-4′, 154.9 C-9, 158.7
- 4: C, 58.93; H, 3.90. Found: C, 58.53; H, 3.84.

32
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33
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34
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36
- 37749001889
- Typical Experimental Procedure: To a mixture of the appropriate 3-bromo-2-styrylchromones 5a-c (0.4 mmol, triphenylphosphine (10.5 mg, 0.04 mmol, tetrakis(triphenylphosphine)palladium(0, 23.1 mg, 0.02 mmol) and triethylamine (55.8 μL, 0.4 mmol) in N-methyl-2-pyrrolidinone (6 mL) was added the appropriate styrene 6a-c (2 mmol for styrene 6a and 0.8 mmol for styrenes 6b,c, The reaction mixture was stirred under different conditions of time and temperature according to the substituents in the compounds (Table 1, Then, the mixture was poured into H2O (20 mL) and ice (10 g) and extracted with Et2O (4 x 25 mL) and dried over anhyd Na2SO4. The residue was evaporated, taken in CH2Cl2 (15 mL) and purified by TLC eluent: CH 2Cl2-light petroleum, 7:3, Two spots were collected in each case: the major one, having higher Rf value, consisted of
- f value, consisted of 2,3-diaryl-3,4-dihydroxanthones 8a-i. The 2,3-diarylxanthones 7a-i were recrystallized from EtOH in yields presented in Table 1.

37
- 37749022293
- Physical Data of 2-(4-Methoxyphenyl)-3-(3,4-dimethoxyphenyl)xanthone (7h, mp 148-150°C 1H NMR (300.13 MHz, CDCl3, δ, 3.60 (s, 3 H, 4″-OMe, 3.80 (s, 3 H, 4′-OMe, 3.90 (s, 3 H, 3″-OMe, 6.61 (d, J, 2.0 Hz, 1 H, H-2″, 6.81 (d, J, 8.8 Hz, 2 H, H-3′, H-5′, 6.83 (d, J, 8.0 Hz, 1 H, H-5″, 6.90 (dd, J, 2.0, 8.0 Hz, 1 H, H-6″, 7.11 (d, J, 8.8 Hz, 2 H, H-2′, H-6′, 7.40 (ddd, J, 0.9, 7.7, 7.8 Hz, 1 H, H-7, 7.52 (dd, J, 0.9, 8.1 Hz, 1 H, H-5, 7.56 (s, 1 H, H-4, 7.75 (ddd, J, 1.7, 7.7, 8.1 Hz, 1 H, H-6, 8.33 (s, 1 H, H-1, 8.37 (dd, J, 1.7, 7.8 Hz, 1 H, H-8, 13C NMR (75.47 MHz, CDCl3, δ, 55.2 (4′-OMe, 55.6 (4″-OMe, 55.8 (3″-OMe, 110.7 (C-5′, 113.2 (C-2″, 113.6 (C-3′, C-5′, 118.0 (C-5, 119.0 (C-4, 120.4 (C-9a, 121.9 C-8a, C-6, 123.9
- 5: C, 76.70, H, 5.06. Found: C, 76.41; H, 5.42.

38
- 37749016482
- Physical Data of 2-(4-Methoxyphenyl)-3-(3,4-dimethoxyphenyl)-3,4- dihydroxanthone (8h, yellow oil. 1H NMR (300.13 MHz, CDCl 3, δ, 2.98 (dd, J, 1.3, 17.2 Hz, 1 H, H-4 trans, 3.62 (dd, J, 8.8, 17.2 Hz, 1 H, H-4 cis, 3.76 (s, 3 H, 3″-OMe, 3.79 (s, 6 H, 4′-OMe, 4″-OMe, 4.22 (dd, J, 1.3, 8.8 Hz, 1 H, H-3, 6.71 (d, J, 8.1 Hz, 1 H, H-5″, 6.81-6.86 (m, 2 H, H-2″, H-6″, 6.83 (d, J, 8.9 Hz, 2 H, H-3′, H-5′, 7.36 (d, J, 8.0 Hz, 2 H, H-5, 7.38 (ddd, J, 1.4, 7.6, 7.7 Hz, 1 H, H-7, 7.44 (s, 1 H, H-1, 7.44 (d, J, 8.9 Hz, 2 H, H-2′, H-6′, 7.60 (ddd, J, 1.6, 7.7, 8.0 Hz, 1 H, H-6, 8.28 (dd, J, 1.6, 7.6 Hz, 1 H, H-8, 13C NMR (75.47 MHz, CDCl3, δ, 36.8 (C-4, 41.4 (C-3, 55.3, 55.75, 55.80 (4′-OMe, 3″-OMe, 4″-OMe, 110.4 C-2″
- 5: 440.1624; found: 440.1624.

39
- 4344580502
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40
- 0345254945
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41
- 37749007480
- Typical Experimental Procedure: A solution of the appropriate 2,3-diarylxanthones 7b-i in freshly distilled CH2Cl 2 (3 mL) was cooled to, 78°C under nitrogen. A solution of BBr3 in 0.1 M CH2Cl2 (2.5 equiv for each methyl group to be cleaved) was gradually added. The reaction mixture was stirred at r.t. for a period of time according to the substituents in the compounds (1 h for each group to be cleaved, After that period, the solution was poured into H2O (20 mL) and vigorously stirred until the formation of a yellow precipitate. The solid was washed abundantly with H2O (4 x 50 mL) and then with light petroleum (4 x 20 mL) to afford the hydroxylated 2,3-diarylxanthones 9b-i in good yields 9b: 72, 9c: 80, 9d: 82, 9e: 94, 9f: 80, 9g: 80, 9h: 94, 9i: 70
- 2O (4 x 50 mL) and then with light petroleum (4 x 20 mL) to afford the hydroxylated 2,3-diarylxanthones 9b-i in good yields (9b: 72%; 9c: 80%; 9d: 82%; 9e: 94%; 9f: 80%; 9g: 80%; 9h: 94%; 9i: 70%).

42
- 37749019413
- Physical Data of 2-(4-Hydroxyphenyl)-3-(3,4-dihydroxyphenyl)xanthone (9h, mp 277-279°C 1H NMR (300.13 MHz, DMSO-d 6, δ, 6.50 (dd, J, 2.0, 8.1 Hz, 1 H, H-6″, 6.62 (d, J, 2.0 Hz, 1 H, H-2″, 6.67 (d, J, 8.1 Hz, 1 H, H-5″, 6.70 (d, J, 8.4 Hz, 2 H, H-3′, H-5′, 6.99 (d, J, 8.4 Hz, 2 H, H-2′, H-6′, 7.50 (dd, J, 7.6, 7.7 Hz, 1 H, H-7, 7.52 (s, 1 H, H-4, 7.68 (d, J, 8.1 Hz, 1 H, H-5, 7.89 (ddd, J, 1.5, 7.6, 8.1 Hz, 1 H, H-6, 8.01 (s, 1 H, H-1, 8.22 (dd, J, 1.5, 7.7 Hz, 1 H, H-8, 8.97 (s, 1 H, 4″-OH, 9.15 (s, 1 H, 3″-OH, 9.51 (s, 1 H, 4′-OH, 13C NMR (75.47 MHz, DMSO-d6, δ =115.1 (C-3′, C-5′, 115.5 (C-5″, 116.9 (C-2″, 118.3 (C-5, 118.9 (C-4, 119.6 (C-9a, 120.8 (C-6″, 121.3 (C-8a, 124.4 (C-7, 126.1 (C-8, 127.0 (C-1, 130.5 C-1′
- 5: 396.0998; found: 396.0996.

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