CASCADE HETEROCYCLIZATION IN THE SYNTHESIS
99
Table 3. IR spectra and 1H NMR spectra of compounds IV, V, IX, XI, XII, XIII, XVI, XVII, and XX
IR spectrum, ν, cm–1
1H NMR, δ, ppm (J/Hz)
Compound
3185 (NH, N+H2);
IV
1.62, 1.85, 2.13, 2.53 (four m, 12H, (CH2)6); 3.02 (m, 4H, N(CH2)2);
2175 (C≡N); 1620 (C=O) 4.84 (s, 1H, C(4)H); 7.12 (m, 3H, H-Ar); 7.21 (d, 1H, H-Ar, 3J = 8.2); 8.33 (s, 1H, NH)
3214 (NH); 2239 (C≡N); 1.95, 2.23, 2.62 (three m, 6H, (CH2)3); 4.59 (s, 1H, C(4)H); 7.16, 7.25
V
(both d, 4H, H-Ar, 3J = 8.1); 10.09 (s, 1H, NH)
1622 (C=O)
IXa
IXb
3155 (NH); 2194 (C≡N); 1.96, 2.22, 2.59 (three m, 6H, (CH2)3); 2.52 (s, 3H, SMe); 5.04 (s, 1H, C(4)H);
7.22 (m, 3H, H-Ar); 7.33 (d, 1H, H-Ar, 3J = 8.2); 9.57 (s, 1H, NH)
1625 (C=O)
1.25 (t, 3H, Me, 3J = 6.5); 1.97, 2.23, 2.58 (three m, 6H, (CH2)3); 2.98 (m, 2H,
3213 (NH); 2203 (C≡N);
1620 (C=O)
SCH2); 5.07 (s, 1H, C(4)H); 7.23 (m, 3H, H-Ar); 7.34 (d, 1H, H-Ar, 3J = 8.2);
9.62 (s, 1H, NH)
1.98, 2.23, 2.59 (three m, 6H, (CH2)3); 3.59, 3.68 (both d, 2H, SCH2, 2J = 14.1);
IXc
IXd
3159, 3308 (NH, NH2);
2193 (C≡N); 1622,
1648 (2C=O)
5.07 (s, 1H, C(4)H); 7.22 (m, 3H, H-Ar); 7.32 (d, 1H, H-Ar, 3J = 8.3); 7.53, 7.88
(both br s, 2H, NH2); 10.69 (s, 1H, NH)
1.96, 2.22, 2.58 (three m, 6H, (CH2)3); 3.81, 3.95 (both d, 2H, SCH2, 2J = 16.2);
5.07 (s, 1H, C(4)H); 7.21 (m, 3H, H-Ar); 7.31 (d, 1H, H-Ar, 3J = 8.2); 7.43, 7.54
(both d, 4H, H-Ar, 3J = 8.3); 10.03, 10.42 (both s, 2H, 2NH)
3154–3318 (2NH);
2192 (C≡N); 1605,
1616, 1624 (2C=O)
IXe
IXf
3390 (NH); 2198
1.92, 2.23, 2.55 (three m, 6H, (CH2)3); 2.51 (s, 3H, SMe); 4.51 (s, 1H, C(4)H);
7.16, 7.28 (both d, 4H, H-Ar, 3J = 8.1); 9.56 (s, 1H, NH)
(C≡N); 1823 (C=O)
1.26 (t, 3H, Me, 3J = 6.7); 1.93, 2.22, 2.57 (three m, 6H, (CH2)3); 2.99 (m, 2H, SCH2);
3214 (NH); 2201 (C≡N);
1638 (C=O)
4.53 (s, 1H, C(4)H); 7.17, 7.28 (both d, 4H, H-Ar, 3J = 8.1); 9.64 (s, 1H, NH)
1.33 (s, 9H, Me3C); 2.31 (s, 3H, Me); 2.51 (m, 4H, CH2NCH2);
3.82 (m, 4H, CH2OCH2); 4.39 [s, 1H, C(4)H]; 7.35, 7.55
(both d, 4H, Ar, 3J = 8.7); 9.45 (br s, 1H, NH)
1.32 (s, 9H, Me3C); 2.29*, 2.38**, 2.42*** (three s, Me); 4.19** (3J = 8.1),
4.28*** (3J = 4.0) (both d, C(4)H); 4.39*** (3J = 4.0), 4.91** (3J = 8.1)
(both d, C(3)H); 4.44* (s, C(4)H); 7.12–7.32 (m, 4H, Ar); 9.53*, 11.94**, 12.13***
(three br s, NH) (major stereoisomer : minor stereoisomer : thiol = 2 : 1 : 2)
3270–3330 (NH, +NH2);
2160 (C≡N); 1708 (C=O)
XI
XII
3240–3255 (NH);
2190, 2253 (C≡N);
1638 (C=O)
XIIIa
XIIIb
3300 (NH); 2194 (C≡N); 1.31 (s, 9H, Me3C); 2.28 (s, 3H, Me); 2.47 (s, 3H, SMe); 4.48 [s, 1H, C(4)H);
7.14, 7.31 (both d, 4H, Ar, 3J = 8.7); 9.15 (s, 1H, NH)
1706 (C=O)
1.24 (t, 3H, MeCH2, 3J = 7.3); 1.29 (s, 9H, Me3C); 2.28 (s, 3H, Me);
3240–3296 (NH);
2200 (C≡N); 1705 (C=O)
2.77, 3.06 (both m, 2H, SCH2); 4.46 (s, 1H, C(4)H); 7.15, 7.32
(both d, 4H, Ar, 3J = 8.6); 9.24 (s, 1H, NH)
1.31 (s, 9H, Me3C); 2.29 (s, 3H, Me); 3.56, 3.65 (both d, 2H, SCH2, 2J = 14.1);
XIIIc
XIIId
3274–3364 (NH, NH2);
2185 (C≡N);
1690–1706 (2C=O)
4.45 [s, 1H, C(4)H]; 7.17 and 7.32 (both d, 4H, Ar, 3J = 8.4); 7.53 and 7.88
(both br s, 2H, NH2); 10.39 (s, 1H, NH)
1.31 (s, 9H, Me3C); 2.31 (s, 3H, Me); 3.81, 3.89 (both d, 2H, SCH2, 2J = 15.4);
3210–3304 (2NH);
2193 (C≡N); 1620,
1684 (2C=O)
4.47 [s, 1H, C(4)H]; 7.16, 7.31 (both d, 4H, 4-ClC H , 3J = 8.5); 7.43, 7.53
6
4
(both d, 4H, 4-BrC H , 3J = 8.4); 9.68, 10.39 (both s, 2H, 2NH)
6
4
3348 (NH, N+H);
0.91 (d, 3H, C(4)Me, 3J = 6.1); 1.65 (s, 3H, C(6)Me); 2.65 (s, 3H, NMe);
XVI
2179 (C≡N); 1692 (C=O) 2.98, 3.74 (both m, 8H, morpholinium fragment); 3.19 (q, 1H, C(4)H,
3J = 6.1); 7.47–7.94 (m, 6H, Ph, N(1)H)
0.98 (d, 3H, C(4)Me, 3J = 6.2); 1.70 (s, 3H, C(6)Me); 2.65 (s, 1H, SMe);
3.39 (q, 1H, C(4)H, 3J = 6.2); 7.57–7.83 (m, 5H, Ph); 9.29 (s, 1H, NH)
1.02 (d, 3H, C(4)Me, 3J = 6.3); 1.73 (s, 3H, C(6)Me); 3.42 (q, 1H, C(4)H, 3J = 6.3);
3.54, 3.67 (both d, 2H, SCH2, 2J = 14.2); 7.43–7.63 (m, 6H, Ph, CONH2);
7.88 (s, 1H, CONH2); 10.31 (s, 1H, NH)
XVIIa
XVIIb
3222 (NH); 2197 (C≡N);
1680 (C=O)
3157–3390 (NH, NH2);
2196 (C≡N); 1695,
1620 (2C=O)
0.98 (d, 3H, C(4)Me, 3J = 6.4); 2.21 (br s, 6H, 2Me); 3.43 (q, 1H, C(4)H,
3J = 6.4); 3.51, 3.64 (both d, 2H, SCH2, 2J = 14.1); 7.52, 7.88
(both s, 2H, CONH2); 10.37 (s, 1H, NH)
XX
3180, 3421 (NH, NH2);
2195 (C≡N); 1708 (2C=O)
Note: An asterisk marks individual thiol signals, two asterisks mark the signals of the major stereoisomer, and three asterisks correspond
to the signals of the minor stereoisomer.
DOKLADY CHEMISTRY Vol. 377
Nos. 4–6
2001