1
Benzodioxane 1 was obtained in 71% yield; mp 94-95°C (ethanol). H NMR spectrum, δ, ppm: 0.91
(2H, m); 1.16 (2H, m) and 2.48 (1H, m) cyclopropane protons; 4.22 (2H, m) and 4.31 (2H, m, OCH2CH2O);
5.89 (2H, br. s, NH2); 6.12 (1H, s, H-5); 7.48 (1H, s, H-8). Found, %: C 65.55; H 5.81; N 6.19. C12H13NO3.
Calculated, %: C 65.74; H 5.96; N 6.39.
Benzodioxane 2 was obtained in 87% yield; mp 124-125°C (ethanol). 1H NMR spectrum, δ, ppm: 4.17
(2H, m) and 4.31 (2H, m, OCH2CH2O); 5.91 (2H, br. s, NH2); 6.21 (1H, s, H-5); 6.91 (1H, s, H-8); 7.21 (1H,
m); 7.32 (1H, m) and 7.41 (2H, m, ArH'). Found, %: C 65.64; H 4.26; N 4.93. C15H12FNO3. Calculated, %:
C 65.93; H 4.43; N 5.13.
6-N-Phenacylamino-7-cyclopropylcarbonyl-1,4-benzodioxane (3) was obtained from amine 1 as
1
described in our previous work [10] in 84% yield; mp 137-138°C (ethanol). H NMR spectrum, δ, ppm: 0.98
(2H, m); 1.18 (2H, m) and 2.51 (1H, m) cyclopropane protons; 3.69 (2H, s, benzyl CH2); 4.25 (2H, m) and 4.33
(2H, m, OCH2CH2O); 7.31 (1H, m) and 7.35 (4H, m, ArH'); 7.58 (1H, s, H-8); 8.31 (1H, s, H-5); 11.61 (1H, s,
NH). Found, %: C 71.01; H 5.42; N 3.91. C20H19NO4. Calculated, %: C 71.20; H 5.68; N 4.15.
6-N-Phenacylamino-7-(m-fluorobenzoyl)-1,4-benzodioxane (4) was obtained analogously from
amine 2 in 91% yield; mp 157-158°C (ethanol). 1H NMR spectrum, δ, ppm: 3.77 (2H, s, benzyl CH2); 4.21 (2H,
m) and 4.34 (2H, m, OCH2CH2O); 7.01 (1H, s, H-8); 7.21-7.45 (9H, m, ArH'); 8.26 (1H, s, H-5); 11.06 (1H, s,
NH). Found, %: C 70.32; H 4.43; N 3.39. C23H18FNO4. Calculated, %: C 70.58; H 4.63; N 3.58.
4-Cyclopropyl-6,7-ethylenedioxy-3-phenyl-2-quinolone (5). Compound 3 (0.67 g, 2 mmol) was added
to a solution of sodium ethylate prepared from sodium (46 mg, 0.002 g-at) and ethanol (25 ml), stirred for 2 h at
20°C, poured into water (120 ml), and neutralized by adding 2 N hydrochloric acid. The precipitate formed was
filtered off, washed with ethanol and ether, and dried in the air to give compound 5 (0.61 g, 91%);
mp 301-302°C. IR spectrum, ν, cm-1: 3000-2400 (N–H), 1640 (C=O). 1H NMR spectrum, δ, ppm: 0.02 (2H, m);
0.65 (2H, m) and 1.95 (1H, m) cyclopropane protons; 4.32 (4H, m, OCH2CH2O); 6.76 (1H, s, H-5); 7.35 (5H,
m, ArH'); 7.57 (1H, s, H-8); 11.55 (1H, s, NH). Found, %: C 74.92; H 5.28; N 4.24. C20H17NO3. Calculated, %:
C 75.22; H 5.37; N 4.39.
6,7-Ethylenedioxy-3-phenyl-4-(m-fluorophenyl)-2-quinolone (6) was obtained in 91% yield (0.35 g)
analogously from compound 4 (0.39 g) upon stirring the reaction mixture for 4 h, mp 354-355°C. IR spectrum,
1
ν, cm-1: 3000-2400 (N–H), 1650 (C=O). H NMR spectrum, δ, ppm: 4.19 (2H, m) and 4.29 (2H, m,
OCH2CH2O); 6.35 (1H, s, H-5); 6.88 (1H, s, H-8); 6.95 (2H, m); 7.06 (6H, m) and 7.31 (1H, m, ArH); 11.80
(1H, s, NH). Found, %: C 73.82; H 4.35; N 3.71. C23H16FNO3. Calculated, %: C 73.98; H 4.32; N 3.75.
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