MODIFIED HANTZSCH REACTION IN THE PRESENCE OF CHIRAL ORGANIC CATALYSTS
705
(OCH3), 102.06 (C), 108.94 (C), 123.03 (2Ph), 128.90
(2Ph), 145.54 (CNO2), 145.87 (CPh), 150.46 (2C),
155.05 (CPh), 167.09 (COO), 194.52 (CO). Found, %:
C 64.81; H 5.90; N 7.54. C20H22N2O5. Calculated, %:
C 64.86; H 5.94; N 7.56.
REFERENCES
1. Cosconati, S., Marinelli, L., Lavecchia, A., and
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vol. 71, p. 217.
3,3,6,6-Tetramethyl-9-(4-nitrophenyl)-3,4,6,7,9,10-
hexahydroacridine-1,8(2H,5H)-dione (2). H NMR
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2008, vol. 10, p. 3627.
spectrum (CDCl3), δ, ppm: 0.98–1.09 s (12H, 4CH3),
2.15–2.44 d.d.d.d (8H, 4CH2, J 16.8, 17.2, 18.0, 18.0 Hz),
5.47 s (1H, CH), 7.11–8.05 d.d (4H, Ph, J 8.4, 8.4 Hz),
11.73 s (1H, NH). 13С NMR spectrum (CDCl3), δ,
ppm: 25.45 (2CH3), 27.16 (2CH3), 29.39 (2C), 31.35
(CH), 44.78 (2CH2), 45.08 (2CH2), 112.71 (2C),
121.82 (2Ph), 122.13 (2Ph), 125.45 (CNO2), 144.04
(2C), 144.73 (CPh), 187.50 (2CO). Found, %: C 70.09;
H 6.63; N 7.16. C23H26N2O4. Calculated, %: C 70.05;
H 6.59; N 7.10.
4. Mekheimer, R.A., Hameed, A.A., and Sadek, K.U.,
Green Chem., 2008, vol. 10, p. 592.
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Martín, N., Quinteiro, M., Seoane, C., Soto, J., Novoa, H.,
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8. Liu, N., Cao, S., Wu, J., Yu, J., Shen, L., Feng, X., and
Dimethyl 2,6-dimethyl-4-(4-nitrophenyl)-1,4-
dihydropyridine-3,5-dicarboxylate (3). 1H NMR
spectrum (CDCl3), δ, ppm: 2.29 s (6H, 2CH3), 3.57 s
(3H, CH3), 5.03 s (1H, CH), 5.83 s (1H, NH), 7.35–
8.02 d.d (4H, Ph, J 8.7, 8.7 Hz). 13С NMR spectrum
(CDCl3), δ, ppm: 18.60 (2CH3), 38.91 (CH), 50.00
(2ОCH3), 101.95 (2C), 122.50 (2CHPh), 127.12
(2CHPh), 143.38 (2CNH), 145.33 (CNO2), 153.16
(CPh), 166.57 (2CO). Found, %: C 58.99; H 5.27; N
8.13. C17H18N2O6. Calculated, %: C 58.96; H 5.20; N 8.09.
Qian, X., Tetrahedron, 2008, vol. 64, p. 3966.
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3,3,6,6-Tetramethyl-9-(4-nitrophenyl)-3,4,5,6,7,9-
hexahydro-1H-xanthene-1,8(2H)-dione (4). 1H NMR
spectrum (400 МHz, CDCl3), δ, ppm: 1.05–1.17 s (12H,
4CH3), 2.17–2.40 d.d.d.d (4H, 2CH2, J 16.9, 17.3,
17.9, 17.9 Hz), 5.44 s (1H, CH), 7.19–8.08 d.d (4H,
Ph, J 8.8, 8.8 Hz). 13С NMR spectrum (100 МHz,
CDCl3), δ, ppm: 24.81 (2CH3), 27.16 (2CH3), 29.11
(2C), 30.70 (CH), 43.49 (2CH2), 44.47 (2CH2), 112.04
(2C), 121.82 (2Ph), 122.49 (2Ph), 125.13 (CNO2),
144.33 (CPh), 145.03 (2C), 186.52 (CO). Found, %: C
69.91; H 6.41; N 3.58. C23H25NO5. Calculated, %: C
69.87; H 6.32; N 3.54.
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2012, vol. 23, p. 1694.
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Detector Absorption Correction Program. Bruker AXS,
Madison, Wisconsin, USA, 2003.
17. Sheldrick, G.M., SHELXTL, v. 6.12, Structure Determina-
tion Software Suite. Bruker AXS, Madison, Wisconsin,
USA, 2001.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 52 No. 5 2016