7
94
D. Kumar, G. Patel, A. Kumar, and R. K. Roy
Vol 46
0
0
0
ꢁ
2-(2 ,6 -Dichlorophenyl)-2,3-dihydro-4(1H)-quinolinone
2e). Viscous liquid lit. [25]; IR (KBr): 3315 (NH), 1640
2-(4 -Chlorophenyl)-2,3-dihydro-4H-chromen-4-one (4e). mp
ꢁ
ꢂ1
1
(
(
95–96 C, lit. [25] 94–95 C; IR (KBr): 1690 (C ¼¼ O) cm ; H
ꢂ1
1
C ¼¼ O) cm ; H NMR (400 MHz, CDCl ): d ¼ 7.89 (d, J ¼
NMR (400 MHz, CDCl ): d ¼ 7.93 (dd, J ¼ 1.76, 7.72 Hz,
3
3
8
.0 Hz, 1H), 7.38–7.20 (m, 4H), 6.76 (t, J ¼ 7.8 Hz, 1H), 6.69
1H), 7.54–7.49 (m, 1H), 7.42–7.41 (m, 4H), 7.09–7.04 (m,
2H), 5.47 (dd, J ¼ 3.0, 12.08 Hz, 1H), 3.04 (dd, J ¼ 3.48,
(
(
d, J ¼ 8.4 Hz, 1H), 5.74 (dd, J ¼ 4.04, 15.24 Hz, 1H), 4.40
br s, 1H, NH), 3.65 (dd, J ¼ 15.42, 16.40 Hz, 1H), 2.59 (dd,
13
13.24 Hz, 1H), 2.88 (dd, J ¼ 3.12, 16.84 Hz, 1H); C NMR
1
3
J ¼ 4.00, 16.40 Hz, 1H); C NMR (CDCl ): d ¼ 193.03,
(CDCl ): d ¼ 191.51, 161.30, 137.27, 136.29, 134.59, 129.04,
3
3
1
1
51.28, 135.87, 135.52, 133.87, 130.09, 129.98, 127.94,
18.62, 118.21, 115.99, 54.17, 40.06.
127.50, 127.09, 121.81, 120.89, 118.08, 78.81, 44.58.
2-(2 ,6 -Dichlorophenyl)-2,3-dihydro-4H-chromen-4-one
0
0
ꢁ
ꢂ1
1
2
-(Furan-2-yl)-2,3-dihydro-4(1H)-quinolinone(2f). [25d,e]
(4f). [25c,e] mp 148–149 C; IR (KBr): 1680 (C ¼¼ O) cm ; H
ꢂ1
1
Viscous liquid; IR (KBr): 3325 (NH), 1690 (C ¼¼ O) cm ; H
NMR (400 MHz, CDCl
7.54–7.50 (m, 1H), 7.41–7.38 (m, 2H), 7.29–7.24 ( m, 1H),
3
): d ¼ 7.97 (d, J ¼ 7.85 Hz, 1H),
NMR (400 MHz, CDCl ): d ¼ 7.85 (d, J ¼ 8.0 Hz, 1H),
3
7
.38–7.26 (m, 2H), 6.79–6.69 (m, 2H), 6.32 (d, J ¼ 1.39 Hz,
H), 6.25 (d, J ¼ 1.53 Hz, 1H), 4.84–4.78 (m, 2H), 3.07–2.92
7.10–7.03 (m, 2H), 6.30 (dd, J ¼ 2.8, 14.8 Hz, 1H), 3.79 (dd,
13
1
J ¼ 3.33, 17.11 Hz, 1H), 2.70 (dd, J ¼ 3.02, 17.02 Hz, 1H);
13
(
m, 2H); C NMR (CDCl
3
): d ¼ 192.72, 153.48, 150.61,
C NMR (CDCl
130.29, 128.10, 127.53, 125.03, 119.40, 118.43, 115.91, 73.71,
37.37.
3
): d ¼ 189.22, 159.12, 134.07, 133.01,
1
1
42.59, 135.54, 127.56, 119.34, 118.69, 116.14, 113.25,
10.49, 50.72, 42.07.
0
Preparation of 2-aryl-2,3-dihydro-4H-chromen-4-one
0
2-(Furan-2 -yl)-2,3-dihydro-4H-chromen-4-one (4g). mp
ꢁ
ꢁ
ꢂ1 1
; H
(
[
4a-g). A neat mixture of 2 -hydroxychalcone (1 mmol) and
bmim]BF (50 mg) was subjected to microwave irradiation at
74–75 C, lit. [27] 80 C; IR (KBr): 1680 (C ¼¼ O) cm
4
NMR (400 MHz, CDCl
3
): d ¼ 7.92 (d, J ¼ 8.0 Hz, 1H),
5
0% power for 2 min with intermittent heating (20 s) and
7.51–7.48 (m, 2H), 7.06-7.01 (m, 2H), 6.46 (d, J ¼ 3.24 Hz,
1H), 6.40 (d, J ¼ 3.05 Hz, 1H), 5.55 (dd, J ¼ 3.28, 11.53 Hz,
1H), 3.27 (dd, J ¼ 11.56, 17.05 Hz, 1H), 2.98 (dd, J ¼ 3.50,
cooling (20 s). After completion of reaction, as indicated by
TLC, the product was extracted into diethyl ether (3 ꢃ 5 mL).
The combined organic phase was distilled off under reduced
pressure. The residue so obtained was percolated through a
bed of silica gel using hexane:ethyl acetate (8:2) as eluent to
afford pure product.
13
16.92 Hz, 1H); C NMR (CDCl
3
): d ¼ 191.24, 160.74,
150.89, 143.43, 136.24, 126.95, 121.73, 120.93, 118.12,
110.51, 109.34, 72.27, 40.80.
General procedure for recovery and reuse of ionic
liquid. After extracting the product using diethyl ether, the
recovered ionic liquid was dried under reduced pressure. The
flask containing recovered ionic liquid (50 mg) was again
charged with 2 -aminochalcone (1 mmol) and following the
aforementioned general procedure, 2-phenyl-2,3-dihydro-
4(1H)-quinolinone 2a was isolated in 81% yield.
2
ꢁ
-Phenyl-2,3-dihydro-4H-chromen-4-one (4a). mp 75–
ꢁ
ꢂ1
1
6 C, lit. [25] 77–78 C; IR (KBr): 1685 cm ; H NMR (400
7
MHz, CDCl
3
): d ¼ 7.94 (dd, J ¼ 1.28,7.8 Hz, 1H), 7.53–7.38
0
(
m, 6H), 7.07–7.04 (m, 2H), 5.48 (dd, J ¼ 2.8, 13.36 Hz, 1H),
3
1
1
4
.09 (dd, J ¼ 13.6, 16.8 Hz, 1H), 2.89 (dd, J ¼ 2.8, 16.8 Hz,
1
3
H); C NMR (CDCl
28.82, 128.74, 127.03, 126.12, 121.59, 120.92, 118.10, 79.57,
3.64.
3
): d ¼ 191.92, 161.53, 138.72, 136.16,
Acknowledgment. Financial supports from BITS, Pilani and
DRDO (No. ERIP/ER/0505034/M/01/902), New Delhi are grate-
fully acknowledged.
2
ꢁ
-(p-Tolyl)-2,3-dihydro-4H-chromen-4-one (4b). mp 82–
ꢁ
ꢂ1
1
3 C, lit. [25] 83–84 C; IR (KBr):1680 cm ; H NMR (400
8
MHz, CDCl
3
): d ¼ 7.9 (dd, J ¼ 2.0, 6.0 Hz, 1H), 7.5 (dd, J ¼
7
7
1
.6, 11.2 Hz, 1H), 7.3 (dd, J ¼ 1.6, 8.0 Hz, 2H,), 7.24 (d, J ¼
.2 Hz, 2H), 7.0 (d, J ¼ 7.2 Hz, 2H), 5.45 (d, J ¼ 13.6 Hz,
H,), 3.09 (dd, J ¼ 2.4, 15.2 Hz,1H), 2.8 (dt, J ¼ 2.4, 16.8
REFERENCES AND NOTES
1
3
[1] (a) Shimokororiyama, M.; In The Chemistry of Flavonoid
Compounds; Geissaman, T. A., Ed.; Pergamon: New York, 1962,
p 286. (b) Harborne, J. B.; Williams, C. A. Nat Prod Rep 1995, 12,
Hz, 1H), 2.30 (s, 3H); C NMR (CDCl ): d ¼ 192.12, 161.64,
3
1
1
38.69, 136.12, 135.77, 129.48, 127.03, 126.18, 121.52,
20.95, 118.14, 79.53, 44.56, 21.17.
6
39. (c) Harborne, J. B., Ed. The Flavonoids. Advances in Research
0
2
-(4 -Methoxyphenyl)-2,3-dihydro-4H-chromen-4-one (4c).
Since 1980; Chapman and Hall: New York, 1988. (d) Flavonoids:
Chemistry, Biochemistry and Applications; Andersen, Ø. M., Mark-
ham, K. R., Eds; Taylor & Francis Ltd.: London, 2006. (e) Chang, L.
C.; Kinghorn, A. D. In Bioactive Compounds from Natural Sources:
Isolation Characterisation and Biological Properties; Tringali, C., Ed.;
Taylor & Francis Ltd.: London, 2001, pp. 159–187.
ꢁ
ꢁ
ꢂ1
mp 87–88 C, lit. [25] 88-89 C; IR (KBr): 1690 (C ¼¼ O) cm
;
1
H NMR (400 MHz, CDCl ): d ¼ 7.93 ( d, J ¼ 7.8 Hz, 1H),
3
7
.50 (dd, J ¼ 1.4, 7.52 Hz, 1H), 7.41 (d, J ¼ 8.6 Hz, 2H),
.06–7.02 (m, 2H), 6.96 (d, J ¼ 8.6 Hz, 2H), 5.43 (dd, J ¼
.72, 13.36 Hz, 1H), 3.83 (s, 3H,), 3.11 (dd, J ¼ 13.44, 16.88
7
2
13
Hz, 1H), 2.86 (dd, J ¼ 2.76, 16.84 Hz, 1H); C NMR
[2] Kalinin, V. N.; Shostakovskii, M. V.; Ponomarev, A. B.
Tetrahedron Lett 1992, 33, 373.
(
CDCl ): d ¼ 192.23, 161.64, 159.99, 136.15, 130.78, 127.73,
3
[
3] (a) Bonhote, P.; Dias, A. P.; Papageorgiou, N.; Kalyanasun-
1
27.03, 121.52, 120.92, 118.13, 114.21, 79.35, 55.36, 44.46.
0
daram, K.; Gratzel, M. Inorg Chem 1996, 35, 1168. (b) Amstrong, D.;
He, W. L.; Liu, Y.-S. Anal Chem, 1999, 71, 3873. (c) Murphy, W. S.;
Watanasin, S. Synthesis, 1980, 647. (d) Edmont, V.; Stoyanov, Y.;
Champavier, A. S.; Basly, J.-P. Bioorg Med Chem Lett, 2002, 12,
2
-(4 -Fluorophenyl)-2,3-dihydro-4H-chromen-4-one (4d).
ꢂ1
ꢁ
ꢁ
mp 96–98 C, lit. [26] 79–80 C; IR (KBr): 1690 (C ¼¼ O) cm
.
1
H NMR (400 MHz, CDCl
.53-7.40 (m, 3H), 7.15-7.02 (m, 3H), 6.97–6.95 (m, 1H), 5.44
3
): d ¼ 7.94 ( d, J ¼ 7.62 Hz, 1H),
7
2
685.
(
dd, J ¼ 14.8, 17.2 Hz, 1H), 3.09 (dd, J ¼ 3.6, 13.2, Hz, 1H),
[
4] (a) Cheng, P. L.; Fournari, P.; Tirouflet, J. Bull Soc Chim
1
3
2
1
1
.92–2.85 (m, 1H); C NMR (CDCl ): d ¼ 192.31, 161.68,
3
Fr 1963, 2248. (b) Ahmed, N.; Lier, J.E.V. Tetrahedron Lett 2001, 47,
2725. (c) Ahmed, N.; Lier, J.E.V. Tetrahedron Lett 2007, 48, 13.
(d) Varma, R.S.; Saini, R.K. Synlett 1997, 857, and references cited
59.38, 136.29, 130.60, 128.08, 128.03, 127.05, 121.78,
20.94, 118.15, 79.41, 44.47.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet