January 2010
Microwave-Assisted Synthesis and Evaluation of Antimicrobial Activity
of 3-{3-(s-Aryl and s-Heteroaromatic)acryloyl}-2H-chromen-2-one Derivatives
185
(0.81 g, 5.3 mmoles), piperidine (0.2 mL). Conditions: MWI
for 1 min, 140ꢀC. Purification: recrystallization (ethanol). kmax
(Log e): 208 (4.03), 244 (3.91), 352 (3.42). IR (KBr): 1740,
183.7 (C¼¼O), 159.4 (C¼¼O), 153.0, 151.5, 147.2, 143.7, 138.9,
134.2, 129.3, 128.3, 127.9, 125.4, 118.1, 116.1, 113.8, 112.7.
MS: m/z 266 (Mþ, 25%), 199 (75%), 68 (33%).
1685, 1600, 1338 cmꢁ1 1H-NMR (CD3OD, 400 Hz): d 3.83
.
3-(3-(5-Nitrofuran-2-yl)acryloyl)-2H-chromen-2-one (3b). Reagents:
Compound 1 (1.0 g, 5.3 mmoles), 5-nitrofurfural (0.47 mL,
5.3 mmoles), piperidine (0.2 mL). Conditions: MWI for 1.5
min, 140ꢀC. Purification: recrystallization (aqueous ethanol,
1:1). kmax (Log e): 216 (4.03), 372 (3.77). IR (KBr): 1734,
(s, 3H, OCH3), 5.35 (s, 1H, OH, D2O exchangeable), 6.79 (d,
1H, Ar-H), 6.99 (d, 1H, Ar-H), 7.03 (d, 1H, J ¼ 8.5 Hz,
COACH¼¼C), 7.16 (s, 1H, Ar-H), 7.42–7.84 (m, 4H, Benzo-
fused coumarin-H), 7.82 (d, 1H, J ¼ 8.5 Hz, COAC¼¼CH),
8.57 (s, 1H, Coumarin-H). 13C-NMR (CD3OD, 400 Hz): d
183.7 (C¼¼O), 159.4 (C¼¼O), 153.0, 149.1 (CAOCH3), 147.9
(CAOH), 147.2, 142.2, 134.2, 128.3, 127.9, 127.6, 125.4,
125.4, 122.9, 118.1, 116.8, 116.1, 111.9, 56.1 (OCH3) ppm.
MS: m/z 323 (Mþ, 68%), 275 (60%), 199 (50%).
1685, 1600, 1376 cmꢁ1 1H-NMR (CD3OD, 400 Hz): d 7.03
.
(d, 1H, J ¼ 8.7 Hz, COACH¼¼C), 7.42–7.85 (m, 5H, Benzo-
fused coumarin-4H & Furan-1H), 7.66 (d, 1H, J ¼ 8.7 Hz,
COAC¼¼CH)), 7.94 (d, 1H, Furan-H), 8.57 (s, 1H, Coumarin-
H). 13C-NMR (CD3OD, 400 Hz): d 183.7 (C¼¼O), 159.4
(C¼¼O), 155.4, 153.8, 153.0, 147.2, 138.9, 134.2, 129.3, 128.3,
127.9, 125.4, 118.1, 117.5, 116.1, 114.5. MS: m/z 311 (Mþ,
20%), 265 (45%).
3-(3-(4-Dimethylaminophenyl)acryloyl)-2H-chromen-2-one
(2i). Reagents: Compound 1 (1.0 g, 5.3 mmoles), 4-(N,N-
dimethylamino)benzaldehyde (1.27 g, 5.3 mmoles), piperidine
(0.2 mL). Conditions: MWI for 2.5 min, 140ꢀC. Purification:
recrystallization (ethanol). kmax (Log e): 208 (4.00), 327
(3.90s), 344 (3.97), 448 (3.84). IR (KBr): 1746, 1685, 1594,
3-(3-(5-Chlorofuran-2-yl)acryloyl)-2H-chromen-2-one (3c). Reagents:
Compound 1 (1.0 g, 5.3 mmoles), 5-chlorofurfural (0.69 g, 5.3
mmoles), piperidine (0.2 mL). Conditions: MWI for 1 min,
140ꢀC. Purification: recrystallization (ethanol). kmax (Log e):
216 (4.28), 368 (4.41), 388 (3.95). IR (KBr): 1744, 1648,
1375 cmꢁ1 1H-NMR (CD3OD, 400 Hz): d 3.06 (s, 6H,
.
2ꢂCH3), 6.71 (d, 2H, Ar-H), 7.03 (d, 1H, J ¼ 8.5 Hz,
COACH¼¼C), 7.72 (d, 2H, Ar-H), 7.42–7.84 (m, 4H, Ar-H),
7.82 (d, 1H, J ¼ 8.5 Hz, COAC¼¼CH), 8.57 (s, 1H, Couma-
rin-H). 13C-NMR (CD3OD, 400 Hz): d 183.7 (C¼¼O), 159.4
(C¼¼O), 153.0, 150.3, 147.2, 142.2, 134.2, 129.7, 129.7, 128.3,
127.9, 125.4, 125.4, 124.7, 118.1, 116.1, 111.7, 111.7, 41.3
(2ꢂCH3) ppm. MS: m/z 319 (Mþ, 70%), 199 (100%).
1
1605, 1380 cmꢁ1. H-NMR (CD3OD, 400 Hz): d 6.89 (d, 1H,
J ¼ 9.3 Hz, Furan-H), 7.03 (d, 1H, J ¼ 8.7 Hz, COACH¼¼C),
7.24 (d, 1H, J ¼ 9.3 Hz, Furan-H), 7.42–7.84 (m, 4H, Benzo-
fused coumarin-H ), 7.66 (d, 1H, J ¼ 8.7 Hz, COAC¼¼CH),
8.57 (s, 1H, Coumarin-H). 13C-NMR (CD3OD, 400 Hz): d
183.7 (C¼¼O), 159.4 (C¼¼O), 153.0, 151.9, 147.2, 138.9, 138.7,
134.2, 129.3, 128.3, 127.9, 125.4, 118.1, 116.1, 114.1, 109.8.
MS: m/z 300.5 (Mþ, 60%), 199 (80%), 103.5 (38%).
3-(5-Phenylpenta-2,4-dienoyl)-2H-chromen-2-one (2j). Reagents:
Compound 1 (1.0 g, 5.3 mmoles), cinnamaldehyde (0.67 mL,
5.3 mmoles), piperidine (0.2 mL). Conditions: MWI for 1 min,
140ꢀC. Purification: recrystallization (ethanol). kmax (Log e):
212 (3.72), 300 (3.49), 330 (3.49), 347 (3.53), 360 (3.53), 366
3-(3-(5-Methylfuran-2-yl)acryloyl)-2H-chromen-2-one
(3d). Reagents: Compound 1 (1.0 g, 5.3 mmoles), 5-methyl-
furfural (0.53 mL, 5.3 mmoles), piperidine (0.2 mL). Condi-
tions: MWI for 2.5 min, 140ꢀC. Purification: recrystallization
(methylated spirit). kmax (Log e): 208 (4.03), 244 (3.91), 352
(3.53), 369 (4.01). IR (KBr): 1740, 1648, 1612, 1375 cmꢁ1
.
1H-NMR (CD3OD, 400 Hz): d 6.69 (d, 1H, J ¼ 8.5 Hz,
(3.42). IR (KBr): 1740, 1685, 1600, 1338 cmꢁ1 1H-NMR
.
COACH¼¼C), 6.71 (d, 1H,
J
¼
8.5 Hz, 9.2 Hz,
(CD3OD, 400 Hz): d 2.30 (s, 3H, CH3), 6.43 (d, 1H, J ¼ 9.5
Hz, Furan-H), 7.03 (d, 1H, J ¼ 8.5 Hz, COACH¼¼C), 7.28
(d, 1H, J ¼ 9.5 Hz, Furan-H), 7.42–7.84 (m, 4H, Benzofused
coumarin-H), 7.66 (s, 1H, COAC¼¼CH). 13C-NMR
(CD3OD, 400 Hz): d 183.7, 159.4, 157.6, 153.0, 152.4, 147.2,
138.9, 134.2, 129.3, 128.3, 127.9, 125.4, 118.1, 117.5,
116.1, 109.5, 13.8 (CH3). MS: m/z 280 (Mþ, 83%), 265
(52%), 68 (30%).
COAC¼¼CACH), 7.02 (d, 1H, J ¼ 9.2 Hz, COC¼¼CAC¼¼CH),
7.52 (d, 1H, J ¼ 8.5 Hz, 9.2 Hz, COAC¼¼CH), 7.33–7.84 (m,
9H, Benzofused coumarin-4H and Ar-5H), 8.57 (s, 1H, Cou-
marin-H). 13C-NMR (CD3OD, 400 Hz): d 183.7 (C¼¼O), 159.4
(C¼¼O), 153.0, 151.9, 147.2, 141.0, 135.2, 134.2, 128.6, 128.6,
128.5, 128.5, 128.3, 127.9, 127.9, 125.4, 125.2, 121.2, 118.1,
116.1 ppm. MS: m/z 302 (Mþ, 55%).
General procedure for synthesis of (3a–e) and (4a–e). A
catalytic amount of piperidine (0.2 mL, 1.64 mmoles) was cau-
tionly added to a well-ground mixture of 3-acetyl coumarin
1(1.0 g, 5.3 mmoles) and substituted heteroaromatic aldehyde
(5.3 mmoles). The reaction mixture was irriadiated in micro-
wave oven at an emitted power of 400 W for an appropriate
time. Then, it was poured in crushed ice and the product was
filtered and recrystallized from appropriate solvent to give 3a–
e and 4a–e.
3-(3-(5-Ethylfuran-2-yl)acryloyl)-2H-chromen-2-one (3e). Reagents:
Compound 1 (1.0 g, 5.3 mmoles), 5-ethyl-2-furaldehyde (0.63
mL, 5.3 mmoles), piperidine (0.2 mL). Conditions: MWI for 2
min, 140ꢀC. Purification: recrystallization (methylated spirit).
kmax (Log e): 212 (4.07), 248 (3.84), 368 (3.42). IR (KBr):
1
1734, 1648, 1606, 1380 cmꢁ1. H-NMR (CD3OD, 400 Hz): d
1.25 (t, 3H, J ¼ 6.0 Hz, CH3), 2.44 (q, 2H, J ¼ 6.0 Hz, CH2),
6.43 (d, 1H, J ¼ 10.0 Hz, Furan-H), 7.03 (d, 1H, J ¼ 8.6 Hz,
COACH¼¼C), 7.28 (d, 1H, J ¼ 10.0 Hz, Furan-H), 7.42–7.84
(m, 4H, Benzofused coumarin-H), 7.66 (d, 1H, J ¼ 8.6 Hz,
COAC¼¼CH), 8.57 (s, 1H, Coumarin-H). 13C-NMR (CD3OD,
400 Hz): d 183.7 (C¼¼O), 159.4 (C¼¼O), 157.4, 153.0, 151.8,
147.2, 138.9, 134.2, 129.3, 128.3, 127.9, 125.4, 120.0, 118.1,
116.1, 108.7, 21.4 (CH2), 12.7 (CH3). MS: m/z 294 (Mþ,
40%). 280 (45%).
3-(3-(Furan-2-yl)acryloyl)-2H-chromen-2-one (3a). Reagents:
Compound 1 (1.0 g, 5.3 mmoles), furfural (0.33 mL, 5.3
mmoles), piperidine (0.2 mL). Conditions: MWI for 3 min,
140ꢀC. Purification: recrystallization (methylated spirit). kmax
(Log e): 220 (3.88), 348 (3.49), 368 (3.65). IR (KBr): 1734,
1648, 1606, 1380 cmꢁ1 1H-NMR (CD3OD, 400 Hz): d 6.87
.
(t, 1H, Furan-H), 7.03 (d, 1H, J ¼ 8.7 Hz, COACH¼¼C),
7.42–7.84 (m, 5H, Benzofused coumarin-4H & Furan-1H),
7.66 (d, 1H, J ¼ 8.7 Hz, COAC¼¼CH), 8.17 (d, 1H, Furan-H),
8.57 (s, 1H, Coumarin-H). 13C-NMR (CD3OD, 400 Hz): d
3-(3-(1H-Pyrrol-2-yl)acryloyl-2H-chromen-2-one (4a). Reagents:
Compound 1 (1.0 g, 5.3 mmol), pyrrole-2-carboxaldehyde
(0.50 g, 5.3 mmol), piperidine (0.2 mL). Conditions: MWI for
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet