TABLE 2 (continued)
1
2
3
2f
3380 (NH2),
3460 (NH2),
1600, 1500,
1220, 745, 685
7.56 (2H, d, 3J = 7.2, H-2',6'); 7.30 (2H, t, 3J = 8.0, H-3',5'); 7.22-7.10
(7Н, m, H-4', H-2''–H-6'', α-H); 7.06 (1H, td, 3J = 7.2, 4J = 0.8, H-4);
6.92 (1H, dd, 3J = 7.6, 4J = 0.8, H-6); 6.79 (1H, d, 3J = 7.2, H-3);
6.77 (1H, d, J = 1.6, β-H); 6.53 (1H, t, 3J = 7.6, H-5); 4.66 (2H, s, NH2)
2g
3465 (OH),
1603, 1454,
1402, 760, 697
9.73 (1H, s, OH); 7.57 (2H, d, 3J = 7.2, H-2',6'); 7.32 (2H, t, 3J = 8.0,
H-3',5'); 7.22 (1H, d, J = 2.0, α-H); 7.19-7.12 (7Н, m, H-4', H-2''–H-6'',
H-4); 7.03 (1H, d, 3J = 8.8, H-6); 6.96 (1H, d, 3J = 8.2, H-3);
6.77 (1H, t, 3J = 8.6, H-5); 6.72 (1H, d, J = 2.0, β-H)
2h
2i
1602, 1497,
1228, 754, 694
7.59 (2H, d, 3J = 7.2, H-2',6'); 7.35-7.25 (6Н, m, Ar–H); 7.22 (1H,
d, J = 1.6, α-H); 7.18-7.10 (6Н, m, Ar–H); 6.80 (1H, d, J = 1.6, β-H);
1.96 (3H, s, CH3)
1700 (C=O),
1600, 1270
(C–O), 745, 680
7.96 (2Н, d, 3J = 8.0, H-3,5); 7.59 (2H, d, 3J = 7.2, H-2',6'); 7.52 (1H,
d, J = 1.6, α-H); 7.33 (4H, m, H-2,6,3',5'); 7.27-7.13 (6Н, m, H-4',
H-2''–H-6''); 6.77 (1H, d, J = 1.6, β-H); 3.86 (3H, s, CH3)
2j
2240 (CN),
1600, 1495,
1230, 755, 694
7.85 (1H, d, 3J = 7.2, H-3); 7.73 (1H, t, 3J = 8.0, H-5); 7.61 (2H, d,
3J = 7.2, H-2',6'); 7.57 (1H, t, 3J = 8.0, H-4); 7.47 (2H, m, α-H, H-6);
7.35 (2H, t, 3J = 8.0, H-3',5'); 7.23-7.17 (4Н, m, H-4', H-3''–H-5'');
7.09 (2H, d, 3J = 7.0, H-2'',6''); 6.86 (1H, d, J = 1.6, β-H)
2k
2l
3433 (OH),
7.93 (2H, m, H-2,4); 7.61 (2H, d, 3J = 7.6, H-2',6'); 7.61 (1H, d,
J = 1.6, α-H); 7.38-7.31 (3H, m, H-6,3',5'); 7.28-7.15 (7H, m,
H-4', H-2''–H-6'', H-5); 6.76 (1H, d, J = 1.6, β-H); 5.0 (br.,
ОН + Н2О)
1670 (C=O),
1602, 1486,
1096, 759, 697
3435 (OH),
1650 (C=O),
1600, 1475,
760, 703
10.85 (1H, br. s, OH); 8.38 (2H, m, H-3,5); 7.92 (1H, d, J = 1.6,
α-H); 7.62 (2H, d, 3J = 7.2, H-2',6'); 7.54–7.42 (3H, m, H-4,3',5');
7.41-7.13 (5H, m, H-4', H-2''–H-6''); 6.95 (1H, d, 3J = 7.2, H-6);
6.75 (1H, d, J = 1.6, β-H)
4a
4b
3027, 2937,
1600, 1358,
1194, 763,
747, 696
7.43 (4H, d, 3J = 8.2, H-2',6'); 7.31-7.24 (10Н, m, H-3'–H-5',
H-3'',5''); 7.10 (2H, t, 3J = 8.0, H-4''); 7.06 (4Н, d, 3J = 8.0,
H-2'',6''); 7.00 (2H, d, J = 1.6, α-H); 6.35 (2H, d, J = 1.6, β-H);
4.18 (4H, s, CH2)
3026, 2938,
1600, 1360,
1190, 763,
745, 690
7.47 (4H, d, 3J = 7.6, H-2',6'); 7.36-7.25 (14Н, m, Ar–H);
7.13 (2H, d, J = 1.6, α-H); 7.10 (2H, t, 3J = 8.0, H-4''); 6.41 (2H, d,
J = 1.6, β-H); 3.91 (4H, t, 3J = 7.0, CH2); 2.04 (2H, q,
3J = 7.0, CH2)
5
1735 (C=O),
1600, 1200
(C–O), 750, 685
7.50 (2H, d, 3J = 7.2, H-2',6'); 7.42–7.27 (7Н, m, Ar–H);
7.24 (1H, d, J = 1.6, α-H); 7.11 (1H, t, 3J = 7.6, H-4''); 6.47 (1H, d,
J = 1.6, β-H); 4.79 (2H, s, CH2); 3.69 (3H, s, OCH3)
_______
* Numbering of H atoms: 1-Ar, 2-6; 2-Ar, 2'-6'; 3, β; 4-Ar, 2"-6"; 5, α.
*2 The spectral data of 2c correspond to data published in [7].
It was also interesting to obtain functionalized N-alkyl-2,4-diphenylpyrroles. For this purpose
ethylenediamine and 1,3-diaminopropane were used in reaction with γ-bromodypnone 1. The reaction takes
place quickly without heat at both amino groups with the formation of 1-[2-(2,4-diphenyl-1H-pyrrol-1-yl)ethyl]-
and 1-[2-(2,4-diphenyl-1H-pyrrol-1-yl)propyl]-2,4-diphenyl-1H-pyrroles 4a,b. Attempts to obtain the products
from cyclization at one amino group using an excess of the amine or the conditions described in [7] (benzene,
without sodium acetate) were unsuccessful.
The reaction of γ-bromodypnone with glycine in the presence of sodium acetate gave the furan 3, while
the reaction with glycine methyl ester gave a mixture of the furan 3 and methyl 2-(2,4-diphenyl-1H-pyrrol-1-
yl)acetate 5, which were purified by fractional crystallization.
744