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LETTER
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Figure 2 ORTEP diagram of 6a
In summary, we described a novel and practical method
for the synthesis of chromenoquinoline derivatives. In ad-
dition to its simplicity, this procedure has the advantage of
high yields, easy availability and flexibility of starting
materials, and short reaction times.18
(17) The CCDC deposition number of 3c is 753403; molecular
formula: C17H13NO2, chemical formula weight 263.28,
monoclinic, unit cell parameters: a = 13.037 (8), b = 7.587
(4), c = 13.158 (8), b = 97.576 (9), space group P21/c.
The CCDC deposition number of 6a is 753401; molecular
formula: C30H13NO, chemical formula weight 283.31,
monoclinic, unit cell parameters: a = 8.6729 (14), b = 15.418
(3), c = 10.8031 (18), b = 106.891 (2), space group P21/c.
The CCDC deposition number of 3b is 753402; molecular
formula: C17H13NO, chemical formula weight 247.29,
monoclinic, unit cell parameters: a = 12.9795 (11), b =
23.1902 (19), c = 8.4440 (7), b = 95.2790 (10), space group
P21/c.
Supporting Information for this article is available online at
Acknowledgment
We gratefully acknowledge DST for financial assistance (Project
number: SR/S1/OC-70/2008) and for providing single-crystal X-
ray diffractometer facility in our school. S.R. and G.V. thank CSIR
for Junior and Senior Research Fellowships.
References and Notes
The CCDC deposition number of 3f is 753404; molecular
formula: C16H10ClNO, chemical formula weight 267.71,
monoclinic, unit cell parameters: a = 31.333 (3), b = 3.8586
(4), c = 40.188 (5), b = 102.334 (4), space group C2/c.
(18) A Typical Procedure for the Preparation of 3a
In a round-bottom flask equipped with a magnetic stirring
bar, aniline (1a, 1.0 mmol), O-propargylated salicylaldehyde
(2a, 1.0 mmol) in MeCN (20 mL), was added La(OTf)3 (10
mol%) and CuI (10 mol%). Reaction mixture was stirred at
reflux temperature of MeCN for 4 h. After completion of the
reaction, as indicated by the TLC, the MeCN was evaporated
and H2O (20 mL) was added to the crude reaction mass.
Then aqueous layer was extracted with CH2Cl2 (3 × 20 mL),
and the combined organic layers were dried over anhyd
Na2SO4, filtered, and concentrated under reduced pressure.
The product was purified by column chromatography on
silica gel (eluent: hexane–EtOAc) afforded 3a (0.210 g,
90%); mp 126 °C. IR (KBr): 3051, 2295, 1649, 1033, 740
cm–1. 1H NMR (400 MHz, CDCl3, TMS): d = 8.48 (1 H, d,
J = 8.0 Hz), 8.11 (1 H, d, J = 8.0 Hz), 7.81 (1 H, s), 7.72 (1
H, d, J = 7.5 Hz), 7.67 (1 H, t, J = 7.5 Hz), 7.46 (1 H, t,
J = 6.5 Hz), 7.36 (1 H, t, J = 7.5 Hz), 7.16 (1 H, t, J = 7.5
Hz), 7.01 (1 H, d, J = 7.5 Hz), 5.32 (2 H, s). 13C NMR (100
MHz, CDCl3, TMS): d = 157.4, 149.0, 148.3, 131.8, 130.9,
129.5, 129.4, 127.5, 127.4, 126.2, 125.5, 125.2, 123.2,
122.5, 117.3 (arom. C); 68.4 (aliph. C). MS (+): m/z = 234
[M + H]. Anal. Calcd for C16H11NO: C, 82.38; H, 4.75; N,
6.00. Found: C, 82.25; H, 4.80; N, 6.12.
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