Mendeleev Commun., 2007, 17, 247–248
AKB is grateful to the Director, NCL, Pune for financial
encouragement and support. KCR is grateful to the Council of
Scientific and Industrial Research (CSIR), New Delhi for a
research fellowship.
support (MLP008626) and to Dr. Mukund K. Gurjar, Head,
Division of Organic Chemistry and Prof. Krishna N. Ganesh,
J. C. Bose Fellow and Director, IISER, Pune for constant
References
†
General experimental procedure. To a mixture of an aldehyde (1 mmol)
1
T. Hideo, Jpn. Tokkyo Koho JP 56005480, 1981 (Chem. Abstr., 1981,
95, 80922b).
and 2-naphthol (2 mmol), methanesulfonic acid (10 mol%) was added, and
the mixture was microwaved (Kenstar Model No. OM-9918C; 2450 MHz,
2350 W) for a specified period (Table 1) in an open vessel. After com-
pletion (TLC), the reaction mass was cooled to room temperature, water
was added and extracted with dichloromethane (3×50 ml). The combined
extracts were dried (anhydrous Na2SO4) and evaporated to dryness. The
crude was subjected to column chromatography (SiO2, 230–400 mesh,
EtOAc–hexane) to furnish pure compounds. All the products were
characterised by spectral data and comparison with authentic samples.
2
R. W. Lambert, J. A. Martin, J. H. Merrett, K. E. B. Parkes and G. J.
Thomas, PCT Int. Appl. WO 9706178, 1997 (Chem. Abstr. 1997, 126,
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3
4
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1
14-Phenyl-14H-dibenzo[a,j]xanthene 3a: H NMR (200 MHz, CDCl3)
d: 6.48 (s, 1H), 6.93–7.13 (m, 3H), 7.36–7.61 (m, 8H), 7.76–7.83 (m,
4H), 8.38 (d, 2H, J 8.8 Hz). 13C NMR (50 MHz, CDCl3) d: 38.1, 117.4,
118.1, 122.7, 124.3, 126.4, 126.8, 128.3, 128.5, 128.8, 128.9, 131.1,
131.5, 145.1, 148.8. IR (CHCl3, n/cm–1): 2923, 1591, 1461, 1377, 1249.
Found (%): C, 90.30; H, 4.98. Calc. for C27H18O (%): C, 90.47; H, 5.06.
14-(3-Methoxyphenyl)-14H-dibenzo[a,j]xanthene 3b: 1H NMR (200 MHz,
CDCl3) d: 3.61 (s, 3H), 6.41 (s, 1H), 6.48–6.53 (m, 1H), 7.01–7.13
(m, 3H), 7.34–7.60 (m, 6H), 7.74–7.82 (m, 4H), 8.38 (d, 2H, J 8.4 Hz).
13C NMR (50 MHz, CDCl3) d: 38.0, 55.1, 111.0, 115.0, 117.2, 118.0,
120.8, 122.8, 124.3, 126.8, 128.8, 128.9, 129.3, 131.1, 131.5, 146.6,
148.8, 159.6. IR (CHCl3, n/cm–1): 3018, 2958, 2933, 1593, 1487, 1458,
1431, 1400, 1251. Found (%): C, 86.45; H, 5.06. Calc. for C28H20O2 (%):
C, 86.57; H, 5.19.
14-(4-Methoxyphenyl)-14H-dibenzo[a,j]xanthene 3c: 1H NMR (200 MHz,
CDCl3) d: 3.57 (s, 3H), 6.41 (s, 1H), 6.64 (d, 2H, J 8.5 Hz), 7.33–7.58
(m, 8H), 7.72–7.81 (m, 4H), 8.35 (d, 2H, J 8.5 Hz). 13C NMR (50 MHz,
CDCl3) d: 37.1, 55.1, 113.9, 117.5, 118.0, 122.7, 124.2, 126.8, 128.8,
128.8, 129.2, 131.1, 131.4, 137.4, 148.7, 157.8. IR (CHCl3, n/cm–1):
3018, 2399, 1602, 1508, 1423, 1215. Found (%): C, 86.46; H, 5.13.
Calc. for C28H20O2 (%):C, 86.57; H, 5.19.
14-(4-Methylphenyl)-14H-dibenzo[a,j]xanthene 3d: 1H NMR (200 MHz,
CDCl3) d: 2.12 (s, 3H), 6.45 (s, 1H), 6.94 (d, 2H, J 8.1 Hz), 7.35–7.61
(m, 8H), 7.75–7.83 (m, 4H), 8.38 (d, 2H, J 8.4 Hz). 13C NMR (50 MHz,
CDCl3) d: 21.0, 37.7, 117.5, 118.1, 122.8, 124.3, 126.9, 128.2, 128.9,
129.3, 131.2, 131.6, 136.0, 142.2, 148.8. IR (CHCl3, n/cm–1): 2943,
2852, 2362, 1591, 1461, 1377, 1242. Found (%): C, 90.12; H, 5.36.
Calc. for C28H20O (%): C, 90.29; H, 5.41.
14-(4-Hydroxy-3-methoxyphenyl)-14H-dibenzo[a,j]xanthene 3e: 1H NMR
(200 MHz, CDCl3) d: 3.64 (s, 3H). 5.32 (s, 1H), 6.42 (s, 1H), 6.71 (d,
1H, J 8.0 Hz), 6.82 (d, 1H, J 2.14 Hz), 7.12–7.16 (m, 1H), 7.37–7.58 (m,
6H), 7.76–7.84 (m, 4H), 8.39 (d, 2H, J 8.30 Hz). 13C NMR (50 MHz,
CDCl3) d: 40.8, 58.9, 114.6, 117.5, 120.8, 121.1, 124.2, 126.0, 127.5,
129.9, 132.0, 134.3, 134.7, 140.2, 147.5, 150.5, 151.9. IR (CHCl3, n/cm–1):
3020, 2399, 1593, 1508, 1431, 1215. Found (%): C, 83.02; H, 4.88.
Calc. for C28H20O3 (%): C, 83.15; H, 4.98.
6
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14-(3-Chlorophenyl)-14H-dibenzo[a,j]xanthene 3f: 1H NMR (200 MHz,
CDCl3) d: 6.46 (s, 1H), 6.94–7.12 (m, 2H), 7.39–7.64 (m, 8H), 7.79–7.86
(m, 4H), 8.32 (d, 2H, J 8.4 Hz). 13C NMR (50 MHz, CDCl3): 37.8, 116.6,
118.1, 122.5, 124.4, 126.5, 126.8, 127.0, 128.4, 129.0, 129.2, 129.7,
131.1, 131.3, 134.4, 147.0, 148.8. IR (CHCl3, n/cm–1): 2918, 2852,
2362, 2335, 1596, 1458, 1377, 1251. Found (%): C, 82.26; H, 4.18.
Calc. for C27H17ClO (%): C, 82.54; H, 4.36.
15 S. C. Baker, Nature, 1991, 350, 627.
1
14-(4-Flourophenyl)-14H-dibenzo[a,j]xanthene 3g: H NMR (200 MHz,
CDCl3) d: 6.48 (s, 1H), 6.77–7.86 (m, 2H), 7.38–7.62 (m, 8H), 7.78–7.86
(m, 4H), 8.34 (d, 2H, J 8.2 Hz). 13C NMR (50 MHz, CDCl3): 37.2, 115.1,
115.6, 117.1, 118.0, 122.5, 124.4, 126.9, 128.9, 129.0, 129.6, 129.7,
131.1, 131.3, 140.8, 140.8, 148.7. IR (CHCl3, n/cm–1): 2952, 2852, 2362,
2331, 1591, 1458, 1377, 1247, 1213. Found (%): C, 86.02; H, 4.28.
Calc. for C27H17FO (%): C, 86.15; H, 4.55.
Received: 15th January 2007; Com. 07/2860
The English language edited by Valentin V. Makhlyarchuk, Moscow
Typeset by Sergei I. Ososkov, Moscow
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