780
K.P. Nandre et al. / Chinese Chemical Letters 22 (2011) 777–780
Acknowledgments
The authors are thankful to the DAE-BRNS (No. 2009/37/39/BRNS/2268), Mumbai, India for financial assistance
and Principal Dr. K.B. Patil, Vice-chancellor, North Maharashtra University, Jalgaon for providing necessary
facilities.
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[15] General method for synthesis of (3): A mixture of an aromatic aldehyde (1.0 mmol), 1,3-cyclohexadionone (2.0 mmol) and 10 mol% CsF in
ethanol (10 mL) was stirred at room temperature for 15–35 min. The progress of the reaction was monitored by thin-layer chromatography,
TLC (eluent, ethyl acetate–hexane 1:1) after completion of the reaction, the white solid precipitated out from ethanol, filtered, washed with
water (25 mL) and purified by recrystallization from ethanol.
[16] General method for synthesis of (4): A mixture of an aromatic aldehyde (1.0 mmol), 1,3-cyclohexadionone (2.0 mmol) and 10 mol% CsF in
ethanol (10 mL) was heated at 80 8C for 60–120 min. The progress of the reaction was monitored by thin-layer chromatography, TLC (eluent,
ethyl acetate–hexane 2:1) after completion of the reaction, ethanol was removed by reduced pressure. Suspended white solid in 3 mol/L HCl,
filtered, washed with water (25 mL) and purified by recrystallization from ethanol.
[17] Spectral data for the selected compounds: 2,20-((3-nitrophenyl)methylene)-dicyclohexane-1,3-dione (3c): 1H NMR (400 MHz, CDCl3): d
12.30 (br s, 2H, OH), 8.01 (d, 1H, J = 8.0 Hz, ArH), 7.57 (s, 1H, ArH), 7.35 (m, 2H, ArH), 5.50 (s, 1H, CH), 2.74–2.58(m, 4H, CH2), 2.52–2.36 (m,
4H, CH2),2.12–2.04(m, 4H, CH2);IR(KBr, cmꢀ1):3316, 2955, 1720, 1627,1516;MS(ESI):m/z357.1(M+);slightyellowsolid;M.P. 196–198 8C.
9-(3-Nitrophenyl)-1,8-dioxooctahydroxanthene (4c): 1H NMR (400 MHz, CDCl3): d 8.0 (d, 1H, J = 7.8 Hz, ArH), 7.86 (s, 1H, ArH), 7.43 (m, 2H,
ArH), 4.88(s, 1H, CH), 2.75–2.59 (m, 4H, CH2), 2.39–2.32 (m, 4H, CH2), 2.12–1.96(m, 4H, CH2);IR(KBr, cmꢀ1): 2953, 2896, 1658, 1517, 1328;
MS(ESI): m/z 339.1(M+); white solid; M.P. 286–288 8C. 2,20-((4-Methoxyphenyl)methylene)-dicyclohexane-1,3-dione (3i): 1H NMR (400 MHz,
CDCl3):d12.35(br s, 2H, OH), 7.08(t, 2H, J = 8.2 Hz, ArH),6.81(d, 2H, J = 8.4 Hz, ArH), 5.45(1, 1H, CH),3.8 (s, 3H, OCH3),2.72–2.54(m, 4H,
CH2), 2.52–2.36 (m, 4H, CH2), 2.1–1.98 (m, 4H, CH2); IR (KBr, cmꢀ1): 3390, 2958, 1722, 1602, 1510; MS(ESI): m/z 342.1(M+); off-white solid;
M.P. 180–182 8C. 9-(4-Methoxyphenyl)-1,8-dioxoocta-hydroxanthene (4i):1H NMR (400 MHz, CDCl3):d 7.22(d, 2H, J = 8.1 Hz, ArH), 6.77 (d,
2H, J = 8.1 Hz, ArH), 4.75 (s, 1H, CH), 3.73 (s, 3H, OCH3), 2.63–2.55 (m, 4H, CH2), 2.37–2.30 (m, 4H, CH2), 2.03–1.98 (m, 4H, CH2); IR (KBr,
cmꢀ1): 2956, 2360, 1720, 1658, 1510; MS(ESI): m/z 324.1(M+); white solid; M.P. 200–202 8C.