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Letters in Organic Chemistry

Volumn 4, Issue 5, 2007, Pages 366-369

Syntheses of the ammonium salts of 7-Carbamate derivatives of quercetin

(7) Wu, Chenglong a Cheng, Li a Li, Ying b Guo, Dong a Yu, Shuyan a Wu, Xianxue c Wei, Yuquan d

a SICHUAN UNIVERSITY (China)

b CHINA WEST NORMAL UNIVERSITY (China)

c YUXI NORMAL UNIVERSITY (China)

d SICHUAN UNIVERSITY (China)

Author keywords

7 carbamate derivatives of quercetin; Ammonium salt; Dichlorodiphenylmethane; Isocyanate; Quercetin

Indexed keywords

EID: 36148929032 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/157017807781212021 Document Type: Article

Times cited : (8)

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23
- 36148998139
- Synthesis of compound 2 and 3 see lit. [9].
- Synthesis of compound 2 and 3 see lit. [9].

24
- 36148978068
- +].
- +].

25
- 36149000299
- 2Ph), 6.34 (d, J=2.0 Hz, 1H, aromatic H), 6.41 (d, J=2.0 Hz, 1H, aromatic H), 6.94 (d, J=8.4 Hz, 1H, aromatic H), 7.15-7.29, (m, 5H, aromatic H), 7.42-7.60 (m, 10H, aromatic H), 7.62 (dd, J=8.4, 3.2 Hz, 1H, aromatic H), 7.63 (d, J=3.2 Hz, 1H, aromatic H). ESI-MS (+): 557.2 [M].
- 2Ph), 6.34 (d, J=2.0 Hz, 1H, aromatic H), 6.41 (d, J=2.0 Hz, 1H, aromatic H), 6.94 (d, J=8.4 Hz, 1H, aromatic H), 7.15-7.29, (m, 5H, aromatic H), 7.42-7.60 (m, 10H, aromatic H), 7.62 (dd, J=8.4, 3.2 Hz, 1H, aromatic H), 7.63 (d, J=3.2 Hz, 1H, aromatic H). ESI-MS (+): 557.2 [M].

26
- 36148968550
- General synthesis of 7-carbamate derivatives of partly protected quercetin. H-Gly-OBzl·Tos 4a (0.895 mmol) was added in a mixture of CH2Cl2-saturated aqueous NaHCO3 30 mL (1:1, The biphasic mixture was cooled in an ice bath and stirred vigorously while BTC (0.320 mmol) was added in a single portion. The reaction mixture was stirred in the ice bath for 10 min, collecting the organic layer, the aqueous layer was extracted with three 5 mL portions of CH2Cl2. The combined organic layers were dried with Na2SO4 1 h and concentrated to give yellow oil 5a. Compound 3 (0.404 mmol) was dissolved in 3 mL THF under argon, then TEA (0.804 mmol) was added, 5a not separated, dissolved in 3 mL THF injecting slowly, then stirred at rt. 5 h. The residue resulting from the solvent evaporation was purified by flash column chromatography using CH2Cl2 to give 6a
- 2 to give 6a.

27
- 36148955540
- Compound 2-(2,2-Diphenylbenzol[1,3]dioxol-5-yl)-3-benzyloxy-7-(benzyl acetate-2-yl)carbamate-5-hydroxychromen-4-one 6a: 1H NMR (400 MHz, CDCl3) δ(ppm, 4.12 (d, J=5.6 Hz, 2H, CH2-(NH), 5.04 (s, 2H, OCH2Ph, 5.24 (s, 2H, OCH2Ph, 5.63 (t, J=5.6 Hz, 1H, NH, 6.58 (d, J=2.0 Hz, 1H, aromatic H, 6.82 (d, J=2.0 Hz, 1H, aromatic H, 6.91 (d, J=8.4 Hz, 1H, aromatic H, 7.12-7.26 (m, 5H, aromatic H, 7.34-7.57 (m, 10H, aromatic H, 7.59 (m, 1H, aromatic H, 7.61 (m, 1H, aromatic H, 12.69 (brs, 1H, 5-OH, ESI-MS, 749.4 [M+2, 2-(2,2-Diphenylbenzo[1,3]dioxol-5-yl)-3- benzyloxy-7-(methyl propionate-2-yl)carbamate-5-hydroxychromen4-one 6b: 1H NMR (400 MHz, CDCl3) δ(ppm, 1.52 (d, J=7.2 Hz, 3H, CH3-(CH), 3.81 (s, 3H, OCH3, 4.46 (m, 1H, CH, NH), 5.04 (s, 2H, OCH2Ph, 5.71 (d, J=7.6, Hz, 1H, NH, 6.58 (d, J=2.0 Hz, 1H, aromatic H, 6.84 d, J=2.0
- 2Ph), 5.87 (d, J=8.4 Hz, 1H, -NH-), 6.56 (d, J=2.0 Hz, 1H: aromatic H), 6.80 (d, J=2.0 Hz, 1H, aromatic H), 6.91 (d, J=8.4 Hz, 1H, aromatic H), 7.12-7.57 (m, 25H, aromatic H), 7.59 (m, 1H, aromatic H), 7.61 (m, 1H, aromatic H), 12.68 (brs, 1H, 5-OH). ESI-MS (+): 910.4 [M].

28
- 36148975465
- Compound 7, acetic-2-yl)carbamate-3,3′,4′,5-tetrahydroxy-chromen- 4-one 7a: ESI-MS, 404.2 [M+1, ESI-MS, 402.0 [M-1, 7-(methyl propionate-2-yl)carbamate-3,3′,4′, 5-tetrahydroxychrom en4-one 7b: ESI-MS, 430.1 [M-1, 7-(3-methylbutyric-2-yl) carbamate-3,3′,4′, 5-tetrahydroxychromen-4-one 7c: ESI-MS, 445.2 [M, ESI-MS, 444.1 [M-1, 7-(4-methylvalerianic-2-r) carbamate-3,3′, 4′,5-tetrahydroxychromen-4-one 7d: 1H NMR (400 MMz, DMSO-d6) δ(ppm, 0.84-0.90 (m, 6H, 2CH3-(CH), 1.45 (m, 1H, CH-(CH3)2, 1.51-1.81 (m, 2H, CH2, 4.36 (m, 1H, CH-(NH), 6.17 (d, J=2.0 Hz, 1H, aromatic H, 6.39 (d, J=2.0 Hz, 1H, aromatic H, 6.88 (d, J=8.4 Hz, 1H, aromatic H, 7.53 (dd, J=8.4, 2.4 Hz, 1H, aromatic H, 7.67 (d, J=2.4 Hz, 1H, aromatic H, 8.21 (brs, 1H, NH, 9.45 brs, 3H, 3-OH, 3′-OH, 4′-OH, 12
- 2-(CH)-), 4.03 (m, 1 H, -CH-(NH)-), 6.19 (d, J=2.0 Hz, 1 H, aromatic H), 6.41 (d, J=2.0 Hz, 1H, aromatic H), 6.88 (d, J=8.4 Hz, 1H, aromatic H), 7.54 (dd, J=8.4, 2.0 Hz, 1H, aromatic H), 7.68 (d, J=2.0 Hz, 1H, aromatic H), 7.89 (brs, 1H, -NH-), 9.44 (brs, 3H, 3-OH, 3′-OH, 4′-OH), 12.50 (s, 1H, 5-OH). ESI-MS (-): 474.0 [M-1].

29
- 36148999138
- General method of deprotection. Compound 6a (0.171 mmol) was dissolved in 15 mL THF-ethanol (1.5:1), 10% Palladium hydroxide was added under a hydrogen flow at room temperature for 24 h. The residue resulting from the solvent evaporation was recrysted in methanol-chloroform to afford 7a.
- General method of deprotection. Compound 6a (0.171 mmol) was dissolved in 15 mL THF-ethanol (1.5:1), 10% Palladium hydroxide was added under a hydrogen flow at room temperature for 24 h. The residue resulting from the solvent evaporation was recrysted in methanol-chloroform to afford 7a.

30
- 36148943654
- Compound 7-(acetic-2-yl)carbamate-3,3′,4′,5-tetrahydroxy- chromen-4-one 7a: 1H NMR (400 MHz, DMSO-d6) 8(ppm, 3.78 (m, 2H, CH2-(NH), 6.18 (d, J, 2.0 Hz, 1H, aromatic H, 6.40 (d, J, 2.0 Hz, 1H, aromatic H, 6.88 (d, J, 8.4 Hz, 1H, aromatic H, 7.54 (dd, J, 8.4, 2.0 Hz, 1H, aromatic H, 7.67 (d, J, 2.0 Hz, 1H, aromatic H, 8.14 (m, 1 H, NH, 9.31 (s, 1 H, 3′-OH, 9.37 (s, 1 H, 3-OH, 9.60 (s, 1H, 4′-OH, 12.50 (s, 1II, 5-OH, ESI-MS, 404.2 [M+1, ESI-MS, 402.0 [M-1, 7-(methyl propionate-2-yl)carbamate-3,3′, 4′,5-tetrahydroxychromen-4-one 7b: 1H NMR (400 MHz, DMSO-d6) 2d(ppm, 1.36 (d, J, 7.2 Hz, 3H, CN3-(CH), 3.67 (s, 3H, OCH3, 4.16 (m, 1H, CH, NH, 6,18 (d, J, 2.0 Hz, 1H, aromatic H, 6.40 (d, J, 2.0 Hz, 1 H, aromatic H, 689 d, J, 8.4 Hz, 1H, aromatic
- 2-(CO)-), 4.03 (m, 1H, -CH-(NH)-), 6.19 (d, J = 2.0 Hz, 1H, aromatic H), 6.41 (d, J = 2.0 Hz, 1H, aromatic H), 6.88 (d, J = 8.4 Hz, 1H, aromatic H), 7.54 (dd, J = 8.4, 2.0 Hz, 1H, aromatic H), 7.68; (d, J = 2.0 Hz, 1H, aromatic H), 7.89 (brs, 1H, -NH-), 9.44 (brs, 3H, 3-OH, 3′-OH, 4′-OH), 12.50 (s, 1H, 5-OH). ESI-MS (-): 474.0 [M-1].

31
- 36148959088
- 3, was then added in the flask. Stirred at room temperature for 1 h, the residue resulting from the solvent evaporation was recrysted in methanol- chloroform to afford 8c (0.097 mmol) in high yield.
- 3, was then added in the flask. Stirred at room temperature for 1 h, the residue resulting from the solvent evaporation was recrysted in methanol- chloroform to afford 8c (0.097 mmol) in high yield.

32
- 36148965917
- Compound 7-(3-methylbutyric-2-yl) carbamate-3,3′, 4′,5-tetrahydroxychromen4-one ammonium 8c: 1H NMR (400 MHz, DMSO-d6) δ(ppm, 0.84 (m, 6H, CH, CH3)2, 1.96 m, 1H, CH-(CH3)2, 3.93 (s, 1H, CH-(NH), 5.76 (s, 1H, NH, 6.18 (d, J, 2.0 Hz, 1H, aromatic H, 6.40 (d, J= 2.0 Hz, 1H, aromatic H, 6.88 (d, J, 8.4 Hz, 1H, aromatic H, 7.54 (dd, J, 8.4, 2.0 Hz, 1H, aromatic H, 7.67 (d, J, 2.0 Hz, 1H, aromatic H, ESI-MS, 444.3 [M-NH4, ESI-MS, 446.3 [M-NH4+2, 7-(4-methyl-valerianic-2-yl)carbamate-3, 3′,4′,5-tetrahydroxychromen4-one ammonium 8d: 1H NMR (400 MHz, DMSO-d6) 2d(ppm, 0.84-0.93 (m, 6H, 2CH3-(CH), 1.37-1.51 (m, 1H, CH-(CH3)2, 1.53,1.74 (m, 2H, CH2, 3.93 (s, 1H, CH-(NH), 5.76 s, 1H, NH
- +2].

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