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R. Cruz-Almanza et al. / Spectrochimica Acta Part A 55 (1999) 1035–1048
121.3 (C-3); 137.8 (C3a); 149.1 (C-4); 141.1 (C-
6); 118.7 (C-7); 147.7 (C-7a); 16.4 (CH3ꢀC-2);
165.0 (COO); 61.8 (CH2Oꢀ); 14.4 (CH3ꢀCH2);
127.0 (C-1%); 160.0 (C-2%) 115.8 (C-3%); 130.0 (C-
4%); 124.5 (C-5%); 132.0 (C-6%).
2985, 2923, 1726, 1712, 1598, 1502, 1390, 1369,
1284, 1143, 1128, 1022, 889. MS m/z (%) 348
M+(55), 276 (100); C20H16O2N2S; MW=348.
Yield 50%. 1HNMR l, ppm 1.50
t J=7
(CH3ꢀCH2ꢀ); 4.52 q J=7 (CH2ꢀOꢀ); 2.73 d
J=1 (CH3ꢀC-2); 8.57 q J=1 (H-3); 8.61 d J=
1 (H-7); 8.70, d J=8.5 (H-3%); 8.32 d J=8.5
(H-4%); 7.88 bd (H-5%); 7.60 ddd J=1.5, 7.0, 8.0
(H-6%); 7.76 ddd J=1.5, 7.0, 8.5 (H-7%); 8.20 bd
J=8.5 (H-8%). 13CNMR l, ppm 146.7 (C-2);
16.6 (CH3ꢀC2); 123.5 (C-3); 136.9 (C-3a); 150.0
(C-4);140.2 (C-6); 119.5 (C-7); 157.3 (C-2%);
121.4 (C-3%); 136.6 (C-4%); 127.9 (C-4%a);127.7 (C-
5%); 127.0 (C-6%); 129.4 (C-7%); 129.7 (C-8%); 165.6
(COO); 61.7 (CH2ꢀOꢀ); 14.4 (CH3ꢀCH2ꢀ).
5.3. 6-Carboethoxy-4-(2%,4%-difluorophenyl)-
thieno[3,2-c]pyridine (5)
Melting point 155-156°C. IR (cm−1)
;
max
2989, 2872, 1727, 1615, 1507, 1316, 1278, 1094,
868. MS m/z (%) 319 M+(63), 248 (100);
1
C16H11NO2SF2 MW=319. Yield 42%. HNMR,
l, ppm; 1.45 t, J=7.0, (CH3ꢀCH2ꢀOꢀ); 4.52, q,
J=7.0 (CH2ꢀOꢀ); 6.97 ddd J=2.5, 9.0, 10.0
(H-3%); 7.07 m, J=0.5, 2.5. 6.5, 10.0 (H-5%); 7.36
ddd J=1.0, 4.0, 5.5 (H-3); 7.70 d, J=5.5 (H-2);
7.73, ddd J=6.5, 8.0, 8.0 (H-6%). 13CNMR, l,
ppm. 130.7 (C-2); 123.6 (C-3); 136.9 (C-3a);
149.6 (C-4); 141.8 (C-6); 119.3 (C-7); 148.0 (C-
7a); 123.5 (C-1%); 162.2 (C-2%); 104.2 (C-3%); 163.7
(C-4%); 112.0 (C-5%); 133.4 (C-6%); 165.5 (COO);
61.9 (CH2ꢀOꢀ); 14.4 (CH3ꢀCH2).
5.6. 6-carboethoxy-4-(2%-carbomethoxy-5%-thieno-
[2,3-b]pyridine)thieno[3,2-c]pyridine (8)
Melting point 214–215°C; IR (cm−1)
;
max
2993, 2956, 1716, 1597, 1510, 1367, 1319, 1269,
1257, 1170, 1076, 852. MS m/z (%) 398
M+(35), 326 (100); C19H14O4N2S2; MW=398.
Yield 43%. 1HNMR l, ppm 1.50
t
q
J=7
J=7
(CH3ꢀCH2ꢀ); 4.0
s
(OCH3); 4.55
5.4. 6-carboethoxy-2-methyl-4-(4%-quinoline)-
thieno[3,2-c]pyridine (6)
(CH2ꢀOꢀ); 7.85 d J=5.5 (H-2); 7.70 dd J=1.0,
5.5 (H-3); 8.70 d J=2(H-4%) 8.74 d J=1 (H-7);
9.19 d J=2 (H-6%); 8.12 s (H-3%). 13CNMR l,
ppm 131.7 (C-2); 122.4 (C-3); 135.6 (C-3a);
151.4 (C-4); 141.6 (C-6); 118.9 (C-7); 148.7 (C-
7a); 149.5 (C-6%); 132.0 (C-3%); 133.4 (C-4%); 134.3
(C-3%a);128.1 (C-3%); 131.9 (C-2%); 163.0 (C-
7%a);162.5 (COOꢀC6); 165.0 (COOꢀ); 14.4
(CH3ꢀCH2ꢀ); 52.6 (MeOOCꢀ); 61.8 (CH2ꢀO).
Melting point 164–165°C. IR (cm−1)
;
max
3080, 2985, 1730, 1712, 1591, 1558, 1517, 1506,
1465, 1436, 1396, 1276, 1176, 1120. MS m/z (%)
348 M+(43), 276 (100); C20H16O2N2S MW=
1
348. Yield 53%. HNMR l, ppm 1.45 t, J=7.0
(CH3ꢀCH2ꢀOꢀ); 4.50 q, J=7.0 (CH2ꢀOꢀ); 2.57
d J=1 (CH3ꢀC2); 6.75 q, J=1 (H-3); 8.70 d
J=1.0 (H-7); 9.06 d J=4.5 (H-2%); 7.57 d, J=
4.5 (H-3%);7.67 bd J=8.0 (H-5%); 7.75 ddd J=
1.5, 6.5, 8.5 (H-7%); 7.47 ddd J=1.0, 6.5, 8.0
(H-6%); 8.21 bd J=8.5 (H-8%). 13CNMR l, ppm
146.8 (C-2); 120.7 (C-3); 138.0 (C-3a); 150.9 (C-
4); 141.1 (C-6); 119.1 (C-7); 148.1 (C-7a); 149.9
(C-2%);121.9 (C-3); 144.8 (C-4%); 166.4 (C-4%a);
125.7 (C-5%); 127.0 (C6%); 129.6 (C-7%); 129.9 (C-
8%); 148.8 (C-8%a); 165.5 (COO); 61.9 (CH2ꢀOꢀ);
14.4 (CH3ꢀCH2ꢀO); 16.3 (CH3ꢀC2).
5.7. 6-carboethoxy-4-(2%Cl,6%-methoxy-3%-
quinoline)thieno[3,2-c]pyridine (9)
Melting point 161–162°C. IR (cm−1)
;
max
3695, 2987, 1730, 1714, 1624, 1595, 1496, 1323,
1274, 1166, 1137, 1033, 854. MS m/z (%) 398
M+(12), 326 (100); C20H15O3N2SCl; MW=398.
1
Yield 63%. HNMR l, ppm 1.47 t J=7 (CH3–
CH2ꢀ); 4.54 q J=7 (CH2ꢀOꢀ); 3.93 s (OCH3ꢀ);
7.72 d J=5.0 (H-2); 7.27 dd J=1.0, 5.0 (H-3);
8.80 d J=1 (H-7); 8.28 bs (H-4%); 7.13 d J=3
(H-5%); 7.46 dd J=3.0, 9.0 (H-7%); 8.08 d J=9
(H-8%). 13CNMR l, ppm 131.2 (C-2); 123.3 (C-3);
137.1 (C-3a); 151.8 (C-4); 141.5 (C-6); 119.8 (C-7);
5.5. 6-carboethoxy-2-methyl-4-(2%-quinoline)-
thieno[3,2-c]pyridine (7)
Melting point 167–168°C. IR (cm−1)
;
max