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5119
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15. CCDC number of the 3i is 720909. These data can be obtained free of charge
16. General procedure for the C-alkylation of 2-hydroxy-1,4-naphthoquinones:
A
mixture of 2-hydroxy-1,4-naphthoquinone (1) (3 mmol) and b-nitrostyrene
(2) (3.6 mmol) was suspended in 5 mL of water, and the reaction mixture was
heated at 80 °C. The progress of the reaction was monitored by TLC. After
completion of the reaction, solid product obtained was filtered and washed with
water (2 Â 10 mL) and n-hexane (3 Â 10 mL). Then the solid was dried under
vacuum to obtain the product (3) in almost pure form. In case of liquid
compounds, the crude reaction mixture was diluted with EtOAc (50 mL) and
washed with water (3 Â 10 mL). The organic layer was dried over anhydrous
MgSO4, followed by evaporation of the solvent to obtain the crude product,
which was passed through a small plug of silica gel to obtain the pure product (3).
17. Spectral data: 2-hydroxy-3-(4-methyl-1-nitropentan-2-yl)naphthalene-1,4-dione
(3a). Light brown solid; mp: 80–82 °C. 1H NMR (400 MHz, DMSO-d6) d 11.48
(br s, 1H), 7.99 (d, J = 7.4 Hz, 2H), 7.87–7.78 (m, 2H), 4.92 (dd, J = 12.3, 9.2 Hz,
1H), 4.75 (dd, J = 12.3, 6.0 Hz, 1H), 4.04–3.96 (m, 1H), 1.46–1.38 (m, 2H), 1.36–
1.29 (m, 1H), 0.86 (d, J = 6.4 Hz, 3H), 0.82 (d, J = 6.4 Hz, 3H). 13C NMR (100 MHz,
DMSO-d6) d 183.9, 180.7, 156.8, 134.7, 133.3, 131.9, 129.8, 126.0, 125.7, 120.7,
77.7, 38.7, 32.1, 25.5, 23.2, 21.7. MS (ESI) (m/z) (relative intensity) 303 (M+, 24),
256 (35), 241 (50), 231 (100), 200 (97), 187 (38). HRMS (ESI) calcd for
C16H17NO5Na (M+Na)+ 326.1015, found: 326.1004. 2-Hydroxy-3-(2-nitro-1-
phenylethyl)naphthalene-1,4-dione (3b). Yellow solid; m.p.: 154–156 °C. 1H
NMR (400 MHz, DMSO-d6) d 11.50 (br s, 1H), 7.94–7.92 (m, 2H), 7.77–7.71 (m,
2H), 7.40 (d, J = 6.9 Hz, 2H), 7.30 (t, J = 6.8 Hz, 2H), 7.21 (d, J = 6.7 Hz, 1H), 5.47
(dd, J = 13.2, 8.7 Hz, 1H), 5.31 (dd, J = 8.7, 6.9 Hz, 1H), 5.16 (dd, J = 13.2, 6.9 Hz,
1H). 13C NMR (100 MHz, DMSO-d6) d 183.8, 180.9, 156.4, 138.5, 134.8, 133.3,
131.7, 129.8, 128.6, 127.9, 127.1, 126.0, 125.8, 120.8, 76.7, 38.6. MS (ESI) (m/z)
(relative intensity) 323 (M+, 13), 322 (100), 275 (77). HRMS (ESI) calcd for
C18H13NO5Na (M+Na)+ 346.0713, found: 346.0691.
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´
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