1294
Russ.Chem.Bull., Int.Ed., Vol. 51, No. 7, July, 2002
Morzherin et al.
NH protons also decreases strongly. For the Z,Zꢀisomer
of 1с the addition of NaI does not result in any substanꢀ
tial changes in the NMR spectra. We can conclude that
the effects observed in the case of the E,Zꢀisomer of 1c
1
Table 3. Н NMR spectra of compounds Z,Zꢀ1f—s and E,Zꢀ1f—s
Comꢀ
pound
δ (J/Hz)
Z,Zꢀ1f 10.23 (t, 1 H, NH); 6.52 (s, 1 H, CH=C(5)); 5.87 (s, 1 H, CH=C(2)); 3.77 (s, 3 H, OMe); 2.51 (d+s, 3 H, NMe)
Z,Zꢀ1g 12.16 (br.s, 1 H, NH); 7.80—7.90 (m, 4 H, ArH); 6.52 (s, 1 H, CH=C(5)); 5.46 (t, 1 H, CH=C(5), J = 7.6);
4.28 (d, 2 H, CH2, J = 7.6); 3.73 (s, 3 H, OMe)
Z,Zꢀ1h 12.18 (s, 1 H, NH); 7.99 (d, 1 H, NH, J = 7.6); 6.48 (s, 1 H, CH=C(5)); 5.87 (s, 1 H, CH=C(2)); 3.76 (s, 3 H,
OMe); 3.40—3.50 (m, 1 H, NCH); 1.00—2.00 (m, 10 H, C5H10)
Z,Zꢀ1i 12.16 (br.s, 1 H, NH); 8.62 (t, 1 H, NH, J = 6.2); 7.20—7.36 (m, 5 H, Ph); 6.50 (s, 1 H, CH=C(5)); 5.94 (s, 1 H,
CH=C(2)); 4.36 (d, 2 H, CH2, J = 6.2); 3.77 (s, 3 H, OMe)
Z,Zꢀ1j 12.29 (s, 1 H, NH); 10.05 (s, 1 H, NH); 7.60 (d, 2 H, ArH, J = 7.4); 7.25 (dd, 2 H, ArH, J = 7.4, J = 8.0); 7.00 (t,
1 H, ArH, J = 8.0); 6.54 (s, 1 H, CH=C(5)); 6.06 (s, 1 H, CH=C(2)); 3.80 (s, 3 H, OMe)
Z,Zꢀ1k 12.36 (br.s, 1 H, NН); 10.05 (s, 1 H, NН); 7.53 (d, 2 H, ArH, J = 9.2); 6.97 (d, 2 H, ArH, J = 9.2); 6.54 (s, 1 H,
СН=С(5)); 6.05 (s, 1 H, СН=С(2)); 3.78 (s, 3 H, OMe); 3.73 (s, 3 H, OMe)
Z,Zꢀ1l 12.4 (br.s, 1 H, NН); 10.15 (s, 1 H, NН); 7.10—7.36 (m, 3 H, ArН); 6.30—6.33 (m, 1 H, ArН); 6.56 (s, 1 H,
СН=С(5)); 6.07 (s, 1 H, СН=С(2)); 3.75 (s, 3 H, OMe); 3.74 (s, 3 H, OMe)
Z,Zꢀ1m 11.6 (br.s, 1 H, NН); 10.09 (s, 1 H, NН); 7.48 (d, 2 H, ArH, J = 8.2); 7.10 (d, 2 H, ArH, J = 8.2); 6.54 (s, 1 H,
СН=С(5)); 6.06 (s, 1 H, СН=С(2)); 3.78 (s, 3 H, OMe); 2.25 (s, 3 H, Me)
Z,Zꢀ1n 12.40 (s, 1 H, NH); 10.10 (s, 1 H, NH); 7.51 (s, 1 H, ArH); 7.38 (d, 1 H, ArH, J = 7.9); 7.18 (dd, 1 H, ArH,
J = 7.9, J = 7.5); 6.86 (d, 1 H, ArH, J = 7.5); 6.55 (s, 1 H, CH=C(5)); 6.08 (s, 1 H, CH=C(2)); 3.79 (s, 1 H,
OMe); 2.28 (s, 3 H, Me)
Z,Zꢀ1o 12.8 (s, 1 H, NH); 10.1 (s, 1 H, NH); 7.62—7.69 (m, 2 H, ArH); 7.08—7.19 (m, 2 H, ArH); 6.56 (s, 1 H, CH=C(5));
6.06 (s, 1 H, CH=C(2)); 3.79 (s, 3 H, OMe)
Z,Zꢀ1p 12.44 (s, 1 H, NH); 10.00 (s, 1 H, NH); 7.95—8.10 (m, 1 H, ArH); 7.10—7.30 (m, 3 H, ArH); 6.56 (s, 1 H,
CH=C(5)); 6.30 (s, 1 H, CH=C(2)); 3.78 (s, 3 H, OMe)
Z,Zꢀ1r 12.70 (s, 1 H, NH); 9.70 (s, 1 H, NH); 8.52 (s, 1 H, ArH); 7.62 (s, 1 H, ArH); 6.55 (s, 1 H, CH=C(5));
6.32 (s, 1 H, CH=C(2)); 3.81 (s, 3 H, OMe)
Z,Zꢀ1s 12.48 (s, 1 H, NH); 10.50 (s, 1 H, NH); 7.90 (d, 9.2, 2 H, ArH); 7.75 (d, 9.2, 2 H, ArH); 6.58 (s, 1 H, CH=C(5));
6.10 (s, 1 H, CH=C(2)); 4.28 (q, 2 H, OMe, J = 7.1); 3.79 (s, 3 H, OMe); 1.31 (t, 3 H, Me, J = 7.1)
E,Zꢀ1f 9.65 (t, 1 H, NH); 6.85 (s, 1 H, CH=C(5)); 5.46 (s, 1 H, CH=C(2)); 3.78 (s, 3 H, OMe); 2.53 (d+s, 3 H, NMe)
E,Zꢀ1g 11.88 (br.s, 1 H, NH); 7.80—7.90 (m, 4 H, ArH); 6.53 (s, 1 H, CH=C(5)); 5.00 (t, 1 H, CH=C(5), J = 7.3);
4.50 (d, 2 H, CH2, J = 7.3); 3.72 (s, 3 H, OMe)
E,Zꢀ1h 12.10 (s, 1 H, NH); 8.02 (d, 7.5, 1 H, NH); 6.72 (s, 1 H, CH=C(5)); 5.45 (s, 1 H, CH=C(2)); 3.77 (s, 3 H, OMe);
3.40—3.50 (m, 1 H, NCH); 1.00—2.00 (m, 10 H, C5H10)
E,Zꢀ1i 12.6 (br.s, 1 H, NH); 8.65 (t, 1 H, NH, J = 6.2); 7.20—7.36 (m, 5 H, Ph); 6.77 (s, 1 H, CH=C(5)); 5.73 (s, 1 H,
CH=C(2)); 4.37 (d, 2 H, CH2, J = 6.2); 3.76 (s, 3 H, OMe)
E,Zꢀ1j 11.79 (s, 1 H, NH); 9.51 (s, 1 H, NH); 7.58 (d, 2 H, ArH, J = 7.6); 7.28 (dd, 2 H, ArH, J = 7.6, J = 7.9); 7.09 (t,
1 H, ArH, J = 7.9); 6.84 (s, 1 H, CH=C(5)); 5.86 (s, 1 H, CH=C(2)); 3.77 (s, 3 H, OMe)
E,Zꢀ1k 12.33 (br.s, 1 H, NН); 9.85 (s, 1 H, NН); 7.52 (d, 2 H, ArH, J = 9.2); 6.87 (d, 2 H, ArH, J = 9.2); 6.69 (s, 1 H,
СН=С(5)); 5.85 (s, 1 H, СН=С(2)); 3.77 (s, 3 H, OMe); 3.72 (s, 3 H, OMe)
E,Zꢀ1l 11.9 (br.s, 1 H, NН); 10.15 (s, 1 H, NН); 7.10—7.36 (m, 3 H, ArН); 6.70 (s, 1 H, СН=С(5)); 6.30—6.35 (m, 1 H,
ArН); 5.70 (s, 1 H, СН=С(2)); 3.79 (s, 3 H, OMe); 3.78 (s, 3 H, OMe)
E,Zꢀ1m 12.38 (br.s, 1 H, NН); 10.08 (s, 1 H, NН); 7.50 (d, 8.2, 2 H, ArH); 7.11 (d, 8.2, 2 H, ArH); 6.70 (s, 1 H,
СН=С(5)); 5.70 (s, 1 H, СН=С(2)); 3.78 (s, 3 H, OMe); 2.25 (s, 3 H, Me)
E,Zꢀ1n 12.00 (s, 1 H, NH); 10.05 (s, 1 H, NH); 7.51 (s, 1 H, ArH); 7.37 (d, 1 H, ArH, J = 7.9); 7.17 (dd, 1 H, ArH,
J = 7.9, J = 7.5); 6.85 (d, 1 H, ArH, J = 7.5); 6.85 (s, 1 H, CH=C(5)); 5.68 (s, 1 H, CH=C(2)); 3.77 (s, 3 H,
OMe); 2.29 (s, 3 H, Me)
E,Zꢀ1o 12.68 (s, 1 H, NH); 10.21 (s, 1 H, NH); 7.62—7.69 (m, 2 H, ArH); 7.08—7.19 (m, 2 H, ArH); 6.71 (s, 1 H,
CH=C(5)); 5.70 (s, 1 H, CH=C(2)); 3.78 (s, 3 H, OMe)
E,Zꢀ1p 12.48 (s, 1 H, NH); 10.00 (s, 1 H, NH); 7.95—8.10 (m, 1 H, ArH); 7.10—7.30 (m, 3 H, ArH); 6.76 (s, 1 H,
CH=C(5)); 5.80 (s, 1 H, CH=C(2)); 3.79 (s, 3 H, OMe)
E,Zꢀ1r 12.57 (s, 1 H, NH); 9.74 (s, 1 H, NH); 8.52 (s, 1 H, ArH); 7.62 (s, 1 H, ArH); 6.78 (s, 1 H, CH=C(5));
5.82 (s, 1 H, CH=C(2)); 3.81 (s, 3 H, OMe)
E,Zꢀ1s 12.00 (s, 1 H, NH); 10.46 (s, 1 H, NH); 7.91 (d, 2 H, ArH, J = 9.2); 7.74 (d, 2 H, ArH, J = 9.2); 6.85 (s, 1 H,
CH=C(5)); 5.95 (s, 1 H, CH=C(2)); 4.27 (q, 2 H, OCH2, J = 7.1); 3.77 (s, 3 H, OMe); 1.25 (t, 3 H, Me, J = 7.1)