1314
Russ.Chem.Bull., Int.Ed., Vol. 53, No. 6, June, 2004
Glukhareva et al.
1
Table 2. H NMR spectra (DMSOꢀd6) of 1,2,3ꢀtriazoleꢀ4ꢀcarbothioamides 1a—z
Comꢀ
pound
δ (J/Hz)
C(5)H
R2
R1
NCH2
Other signals
1a
1b
8.40
8.77
13.94 (br.s, 1 H, ОH)
4.25 (s, 3 H, OCH3)
3.76 (t, 2 H, NCH2, J = 4.6);
3.68 (t, 2 H, NCH2, J = 4.6)
3.77 (t, 2 H, NCH2, J = 4.9);
3.67 (t, 2 H, NCH2, J = 4.9)
4.30 (t, 2 H, ОCH2, J = 4.6);
4.07 (t, 2 H, ОCH2 J = 4.6)
4.20—4.35 (m, 2 H, OCH2);
4.03 (t, 2 H, OCH2, J = 4.9)
1c
1d
8.83
8.77
11.88 (br.s, 1 H, NH); 8.92 (d, 1 H,
ArH, J = 2.8); 8.35 (dd, 1 H, ArH, J =
9.5, J = 2.8); 6.46 (d, 1 H, ArH, J = 9.5)
7.67 (dd, 1 H, ArH, J = 6.7, J = 1.8);
7.55 (ddd, 1 H, ArH, J = 7.6, J = 7.9,
J = 1.5); 7.33 (ddd, 1 H, ArH, J = 7.6,
J = 7.8, J = 1.6); 7.16 (dd, 1 H, ArH,
J = 7.6, J = 1.2); 3.87 (s, 3 H, OMe)
7.77—7.72 (m, 2 H, 2 ArH); 7.29—7.81
(m, 2 H, 2 ArН)
3.81 (t, 2 H, NCH2, J = 4.6);
3.75 (t, 2 H, NCH2, J = 4.6)
4.35 (t, 2 H, ОCH2, J = 4.6);
4.12 (t, 2 H, ОCH2, J = 4.6)
3.79 (t, 2 H, NCH2, J = 4.6);
3.71 (t, 2 H, NCH2, J = 4.6)
4.35 (t, 2 H, OCH2, J = 4.6);
4.12 (t, 2 H, OCH2, J = 4.6)
1e
1f
8.55
8.14
8.86
8.58
3.94—3.82 (m, 4 H, N(СH2)2)
4.48—4.38 (m, 4 H, O(СH2)2)
4.09 (s, 3 H, Me)
3.89 (t, 2 H, NCH2, J = 4.6);
3.82 (t, 2 H, NCH2, J = 4.6)
3.82 (t, 2 H, N(СH)2 J = 4.5);
3.75 (t, 2 H, N(СH)2, J = 4.5)
4.42 (t, 2 H, OCH2 J = 4.6);
4.35 (t, 2 H, OCH2, J = 4.6)
4.37 ( t, 2 H, О(CH)2, J = 4.5);
4.10 (t, 2 H, О(СH)2, J = 4.5)
4.46 (t, 2 H, O(CH)2, J = 4.8);
4.40 (t, 2 H, O(CH)2, J = 4.8);
3.93—3.84 (m, 7 H,
1g
1h
8.05—7.78 (m, 4 H, ArH)
7.43 (dd, 1 H, ArH, J = 8.1, J = 8.1); 7.26—7.34
(m, 2 H, 2 ArH); 7.0 (dd, H, ArH, J = 6.3, J = 1.5);
3.93—3.84 (m, 7 H, OCH3 and N(СН2)2)
Me and N(СН2)2)
1i
8.50
8.52
8.91
7.65 (d, 2 H, 2 ArH, J = 9.2); 7.03 (d,
2 H, 2 ArH, J = 9.2); 3.85 (s, 3 H, OCH3) 3.72 (t, 2 H, N(СH)2, J = 4.4)
4.40—4.55 (m, 1 H, СH); 2.00—2.20 (m, 3.76 (t, 2 H, N(СH)2, J = 4.9); 4.31 (t, 2 H, О(CH)2, J = 4.9);
2 Н, СН2); 1.20—2.00 (m, 8 Н, 4 (СН2)) 3.68 (t, 2 H, N(СH)2, J = 4.9)
3.80 (t, 2 H, N(СH)2, J = 4.4); 3.75—3.88 (m, 4 Н, О(CН2)2)
1j
4.10 (t, 2 H, О(СH)2, J = 4.9)
3.81 (t, 2 Н, N(СН)2, J = 4.8); 4.36 (t, 2 H, O(СН)2, J = 4.8);
3.72 (t, 2 Н, N(СН)2, J = 4.8) 4.08 (t, 2 Н, O(СН)2, J = 4.8)
1k
7.88 (ddd, 1 H, ArH, J = 6.4, J = 6.0,
J = 1.6); 7.56—7.66 (m, 2 H, 2 ArH);
7.10 (dd, 1 H, ArH, J = 7.6, J = 7.6)
10.53 (уш.s, 1 H, ОH); 7.69 (dd, 1 H,
ArH, J = 8.0, J = 1.2); 7.29 (ddd, ArH,
J = 8.0, J = 8.0, J = 1.6); 7.12 (dd,
1 H, ArН, J = 7.2, J = 1.2); 6.97 (ddd,
1 Н, ArН, J = 7.2, J = 8.0, J = 1.2)
7.96 (d, 2 H, 2 ArH, J = 8.8); 7.72 (d,
2 H, 2 ArH, J = 8.8)
7.39—7.35 (m, 5 H, Ph); 5.62 (s, 2 H,
СН2)
12.00 (br.s, 1 H, NH); 7.62 (d, 2 H,
2 ArH, J = 8.5); 7.44 (d, 2 H, 2 ArH,
J = 8.5); 2.42 (s, 3 Н, Me)
1l
8.74
3.83 (t, 2 Н, N(СН)2, J = 4.4); 4.36 (t, 2 Н, O(СН)2, J = 4.8);
3.77 (t, N(СН)2, J = 4.8) 4.26 (t, 2 Н, O(СН)2, J = 4.4)
1m
1n
1o
8.55
8.59
8.42
3.83 (t, 2 Н, N(СН)2, J = 4.8); 4.36 (t, 2 H, O(CH)2, J = 4.8);
3.75 (t, 2 Н, NСН2, J = 4.7) 4.15 (t, 2 H, O(CH)2, J = 4.6)
3.76 (t, 2 H, N(CH)2, J = 4.8); 4.31 (t, 2 H, O(СH)2, J = 4.9);
3.67 (t, 2 H, N(CH)2, J = 4.9) 4.11 (t, 2 H, О(СH)2, J = 4.8)
3.76 (t, 2 H, N(CH)2, J = 4.9); 4.28 (t, 2 H, О(CH)2, J = 4.9);
3.67 (t, 2 Н, N(СН)2, J = 4.9)
3.91 (t, 2 H, О(CH)2, J = 4.9)
1p
1q
8.55
8.08
7.65 (d, 2 H, 2 ArH, J = 8.0); 7.61 (d,
2 H, 2 ArH, J = 8.0); 2.43 (s, 3 H, Me)
3.83—3.93 (m, 4 H, N(CH2)2)
4.38—4.47 (m, 4 H, O(СН2)2)
7.33—7.41 (m, 5 H, Ph); 5.45—5.43 (m, 3 H, СH2 and NCH);
5.15 (d, 1 H, NCH, J = 6.5); 3.04 (dd, 1 H, NCH, J = 13.1,
J = 10.7); 2.83 (dd, 1 H, NCH, J = 13.1, J = 10.7)
3.73—3.81 (m, 2 H, O(CH)2);
1.21 (d, 3 H, Me, J = 6.1)
1r
9.11
7.84 (d, 2 H, 2 ArH, J = 8.2); 7.41 (d,
2 H, 2 ArH, J = 8.2); 2.39 (s, 3 Н, Me)
5.36 (dd, 1 H, NCH, J = 13.2,
J = 0.6); 4.54 (d, 1 H, NCH,
3.63—3.72 (m, 2 H, О(CH)2);
1.22 (d, 3 H, Me, J = 6.4);
J = 13.2); 3.13 (dd, 1 Н, NCH, 1.19 (d, 3 H, Me, J = 6.1)
J = 12.8, J = 10.7); 2.93 (dd,
1 Н,NCH, J = 12.8, J = 10.7)
(to be continued)