Nov-Dec 2007
Synthesis and Reactions of Some New Allyl Furobenzopyranone Derivatives
1313
Table 2 (continued)
No
4a
Spectral data
ir (Cm-1) ꢀ = 3600 (OH), 1620 (C=O), 1580 (C=C).
1H nmr (CDCl3) ꢁ: (d, 2H, 2H-1', J = 4.68 Hz), 4.09 (s, 3H, OCH3), 5.02 (dd, 1H, 1H-3', Jgem= 1.83 Hz, Jcis= 10.15 Hz), 5.11
(dd, 1H, 1H-3', Jgem= 1.83 Hz, Jtrans= 15.43 Hz), 6.07 (m, 1H, H-2'), 6.86 (d, 1H, H-3) , 7.38-7.91 (m, 8H, Ar-H, ꢂ-H, ꢃ-H, H-
2), and 12.96 ppm (s, 1H, OH).
4b
ir (Cm-1) ꢀ = 3600-3470 (br,OH) , 1624 (C=O), 1603 (C=C), 1546 (Ar.).
1H nmr (CDCl3) ꢁ: 3.62 (d, 2H, 2H-1', J = 4.88 Hz) , 3.86 (s, 3H, OCH3), 4.09 (s, 3H, OCH3), 5.04 (dd, 1H, 1H-3', Jgem= 1.80
Hz, Jcis= 10.17 Hz)), 5.12 (dd, 1H, 1H-3', Jgem= 1.80 Hz, Jtrans= 17.13 Hz), 6.75 (m, 1H, H-2'), 6.80-7.87 (m, 8H, Ar -H and ꢂ,ꢃ-
H),13.11 (s, 1H, OH).
ms m/z (%) 365 (m+1)+(13), 364 (m)+ (58) , 324 (16) [M-(cyclopropene), 230 (75), 215 ( 39), 203 (20) , 201 (31), 190 (99.9)[
M-(cyclopropene, 4-methoxy styryl)], 187(34), 173 (100) , 161 (30), 147 (39), 145 (49), 91 (76) and 78 ppm (86).
ir (Cm-1) ꢀ = 3520(OH), 1650 (C=O), 1585 (C=C).
4c
1H nmr (CDCl3) ꢁ: 3.64 (d, 2H, 2H-1', J = 5.11 Hz), 4.11 (s, 3H, OCH3), 5.00 (dd,1H, 1H-3', Jgem= 1.82 Hz, Jcis= 10.22 Hz),
5.16 (dd,1H, 1H-3', Jgem= 1.82 Hz, Jtrans= 17.33 Hz), 6.08 (m, 1H, H-2'), 6.88 (d, 1H, H-3) , 7.38-7.91 (m, 9 H, Ar-H, ꢂ-H, ꢃ-H)
and 13.09 ppm (s, 1H, OH).
4d
ir (Cm-1) ꢀ = 3650-3500 (br, OH), 1627 (C=O), 1526 (C=C).
1H nmr (CDCl3) ꢁ: 3.05 (s, 6H , N(CH3)2 ) , 3.62 (d, 2H, 2H-1') 4.06 (s, 3H, OCH3), 5.02 (dd, 1H, 1H-3', Jgem= 1.56 Hz, Jcis
=
10.04 Hz), 5.10 (dd, 1H, 1H-3', Jgem= 1.58 Hz, Jtrans= 17.08 Hz), 6.08 (m, 1H, H-2'), 6.70 (d, 2H, H-3",5" J = 8.8 Hz), 6.86 (d,
1H, H-3, J= 2.3 Hz), 7.49 (d, 1H, H-2, J= 2.3 Hz), 7.56 (d, 2H, H-2", 6", J= 8.4 Hz), 7.74 (d, 1H, H-ꢀ, J = 15.4 Hz) 7.90 (d,
1H, H-ꢄ, J = 15.4 Hz) and 13.31 ppm (s, 1H, OH)
ms m/z (%) 378 (m+1)+ (2) , 377 (m+) (8), 337 (23) [M-(cyclopropene), 230 (55), 215 ( 39), 190 (99.9)[ M-(cyclopropene, 4-
N,N-dimethyl styryl)].
ir (Cm-1) ꢀ = 1670 (C=O), 1600 (C=C), 1590 (Ar).
6
1H nmr (CDCl3) ꢁ: 3.80 (s, 3H, OCH3), 4.05 (s, 3H, OCH3), 4.56 (d, 2H, 2H-1', J = 4.53 Hz), 5.31 (dd, 1H, 1H-3', Jgem= 2.12
Hz, Jcis= 10.30 Hz), 5.43 (dd, 1H, 1H-3', Jgem= 2.10 Hz, Jtrans= 17.19 Hz), 6.08 (m, 1H, H-2',), 6.70 (s, 1H, H-7), 6.88 (d, 1H, H-
3, J= 2.07 Hz), 7.11-7.39 (m, 4H, Ar-H) and 7.49 ppm (d,1H, H-2, J = 2.07 Hz).
ir (Cm-1) ꢀ = 3500-3450 (br, OH, NH), 1580 (Ar).
7a
1H nmr (CDCl3) ꢁ: 1.01 (t, 3H, CH3CH2CH2, J = 7.36 Hz), 1.70 (m, 2H, CH3CH2CH2), 2.87 (t, 2H, CH3CH2CH2, J = 7.45 Hz),
3.40 (dd, 1H, CH2 of pyrazoline, J = 9.08 Hz, 8.98 Hz), 3.82 (dd, 1H, CH2 of pyrazoline, J = 10.45 Hz), 3.96 (s, 3H, OCH3),
4.82 (t, 1H, CH of pyrazoline, J = .9.65), 5.85 (s, br., 1H, NH), 6.80 (m, 1H, H-4 phenyl group), 7.29-7.46 (m, 6H, Ar.H), and
12.38 ppm (s, 1H, OH).
7b
ir (Cm-1) ꢀ = 3520 (OH), 1588(C=C), 1579 (Ar).
1HNMR (CDCl3) ꢁ: 3.33 (d, 2H, 2H-1', J= 5.02 Hz), 3.45 (dd, 1H, CH2 of pyrazoline, J = 9.05 Hz, 8.95 Hz), 4.07 (s, 3H,
OCH3) , 4.18 (dd, 1H, CH2 of pyrazoline, J = 10.40 Hz), 4.89 (t, , 1H, CH of pyrazoline, J = 9.75), 5.03 (dd, 1H, H-3', Jgem
=
1.59 Hz, Jcis=10.23 Hz) , 5.14 (dd,1H, H-3', Jgem= 1.67 Hz, Jtrans= 16.87 Hz) , 6.12 (m, 1H, H-2'), 7.01 (d, 1H, H-3), 6.89-7.30
(m, 10H , Ar.-H ), 7.49 (d, 1H, H-2), and 12.18 ppm (s, br, 1H, OH).
7c
7d
7e
ir (Cm-1) ꢀ = 3510-3470 (br, OH, NH ), 1590 (C=C), 1580 (Ar).
1HNMR (CDCl3) ꢁ: 0.98 (t, 3H, CH3CH2CH2, J = 7.33 Hz), 1.75 (m, 2H, CH3CH2CH2), 2.83 (t, 2H, CH3CH2CH2, J = 7.41 Hz),
3.35 (dd, 1H, CH2 of pyrazoline, J = 9.18 Hz), 3.80 (dd, 1H, CH2 of pyrazoline, J = 10.55 Hz, 10.73 Hz), 3.90 (s, 3H, OCH3),
4.80 (t, 1H, CH of pyrazoline, J = .9.60), 5.80 (s, br., 1H, NH), 6.79-7.53 (m, 6H , Ar.-H ), and 12.18 ppm (s, 1H, OH).
ir (Cm-1) ꢀ = 3560 (OH), 15810 (C=C), 1577 (Ar).
1H nmr (CDCl3) ꢁ: 3.42 (dd, 1H, CH2 of pyrazoline, J = 9.28 Hz), 3.70 (d, 2H, 2H-1', , J= 4.81 Hz), 4.00 (s, 3H, OCH3) , 4.20
(dd, 1H, CH2 of pyrazoline, J = 10.44 Hz), 5.00-5.10 (m, 3H, CH of pyrazoline ,2x H-3'), 6.14 (m, 1H, H-2'), 6.80-7.50 (m,
11H, Ar.-H ), and 12.04 ppm (s,1H, OH).
ir (Cm-1) ꢀ = 3540-3500 (br, OH, NH), 1583 (Ar).
1H nmr (CDCl3) ꢁ: 1.0 (t, 3H, CH3CH2CH2, J = 7.38 Hz), 1.67 (m, 2H, CH3CH2CH2), 2.86 (t, 2H, CH3CH2CH2, J = 7.49 Hz),
2.94 (s, 6H, 2 x CH3), 3.40 (dd, 1H, CH2 of pyrazoline, J = 9.03 Hz, 8.88 Hz), 3.74 (dd, 1H, CH2 of pyrazoline, J = 10.85 Hz),
3.97 (s, 3H, OCH3), 4.74 (t, 1H, CH of pyrazoline, J = .9.15), 5.80 (s, br., 1H, NH), 6.71 (d, 2H, H-3",5", J = 8.6 Hz), 6.79 (d,
1H, H-3, J = 2.2 Hz), 7.25 (d, 2H, H-2", H-6", J = 8.6 Hz), 7.45 (d, 1H, H-2, J = 2.2 Hz) and 12.33 ppm (s, 1H, OH).
ir (Cm-1) ꢀ = 3530 (OH), 1590 (C=C), 1588 (Ar).
7f
1H nmr (CDCl3) ꢁ: 2.85 (s, 6H, 2 x CH3 ), 3.30 (d, 2H, 2H-1', J = 4.90 Hz), 3.40 (dd, 1H, CH2 of pyrazoline, J = 9.00 Hz, 9.08
Hz), 3.99 (s, 3H, OCH3) , 4.20 (dd, 1H, CH2 of pyrazoline, J = 10.45 Hz), 5.00 (t, 1H, CH of pyrazoline, J = .9.65), 5.05 (dd,
1H, H-3', Jgem= 1.86 Hz, Jcis= 9.97 Hz) , 5.22 (dd, 1H, H-3', Jgem= 1.89 Hz, Jtrans=17.18 Hz) , 6.00 (m, 1H, H-2'), 6.90 (d, 1H, H-
3), 6.89-7.30 (m, 9H , Ar.-H ), 7.80 (d, 1H, H-2) and 12.10 ppm (s,1H, OH).
ir (Cm-1) ꢀ = 3421 (br., OH ), 3109 (CH), 1659 (C=O), 1600 (C=C), 1585 (Ar).
9
1H nmr (CDCl3) ꢁ: 2.40 (s, 3H, CH3) , 3.69 (d, 2H, 2H-1, J = 4.92 Hz), 5.00 (dd, 1H, H-3', Jgem= 1.54 Hz, Jcis= 9.89 Hz), 5.04
(dd, 1H, H-3', Jgem= 1.60 Hz, Jtrans=17.23 Hz) , 5.98 (m, 1H, H-2'), 6.09 ( s, 1H , H-6) , 6.97 (d, 1H, H-3, J = 2.4 Hz), 7.58 (d,
1H, H-2, J = 2.4 Hz) and 13.45 ppm (s,1H, OH).
ir (Cm-1) ꢀ = 3100 (CH), 1670 (C=O), 1605 (C=C, Ar).
11
13
1H nmr (CDCl3) ꢁ: 2.33 (s, 3H, CH3), 4.97 (d, 2H, 2H-1'', J = 4.76 Hz), 4.79 (dd, 1H, H-3' Jgem= 2.2 Hz, Jcis=10.36 Hz) , 5.47
(dd, 1H, H-3' Jgem=2.2 Hz, Jtrans= 17.15 Hz) , 6.03 ( s, 1H , H-6) , 6.18 (m, 1H, H-2'), 6.95 (d, 1H, H-3, J = 2.36 Hz) and 7.58
ppm (d, 1H, H-2, J = 2.36 Hz).
ir (Cm-1) ꢀ = 3317(br, sharp, OH), 1785 (lactone COO), 1643 (C=C), 1596 (Ar. ).
1H nmr (CDCl3) ꢁ: 3.61 (d, 2H, 2H-1', J= 5.03Hz), 4.32 (s, 3H, OCH3), 5.02 (dd, 1H, 1H-3', Jgem= 1.44 Hz, Jcis= 9.90 Hz), 5.08
(dd, 1H, 1H-3', Jgem=1.46 Hz, Jtrans= 16.65 Hz), 6.03 (m, 1H, H-2'), 6.87 (d, 1H, H-3, J = 2.46 Hz), 7.55 (d, 1H, H-2, J = 2.46
Hz), 11.5 (s, br., 1H, H-6) and 12.40 ppm (s, 1H, OH).