SYNTHESIS OF NOVEL BI-HETEROCYCLES
595
and the products (VIIa–m) were filtered, washed with 163.05 (C-2), 143.90 (C-4), 138.61 (C-1'''), 128.70
distilled water and dried for further use.
(C-3'' and C-5''), 123.64 (C-4'''), 119.15 (C-2''' and C-6'''),
103.13 (C-5), 36.67 (C-2''), 27.53 (C-6); EI MS: m/z
375 [M]+, 301 [[C15H15N3O2S]+, 262 [C12H12N3O2S]+,
2-({5-[(2-Amino-1,3-thiazol-4-yl)methyl]-1,3,4-
oxadiazol-2-yl}sulfanyl)-N-benzylacetamide (VIIa).
Light brown solid; Yield: 89%; mp: 229–230°C; Mol.
Formula: C15H15N5O2S2; Mol. Mass.: 361 g mol–1; IR:
3345 (N–H stretching), 3050 (C–H of aromatic ring),
2915 (–CH2– stretching), 1675 (C=O stretching ),
1570 (C=C stretching of aromatic ring), 1515 (C=N
stretching); 1H NMR: 10.37 (s, 1H, N–H), 7.56 (br.d,
J = 8.0, 2H, H-2''' & H-6'''), 7.32 (br.t, J = 7.8, 2H, H-
3''' and H-5'''), 7.07 (br.t, J = 7.2, 1H, H-4'''), 6.99
(2H, –NH2), 6.39 (s, 1H, H-5), 4.26 (s, 2H, CH2-2''),
235 [C11H11N2O2S]+, 195 [C10H13NOS]+, 163
[C10H13NO]+, 141 [C5H5N2OS]+, 121 [C8H11N]+, 114
[C4H6N2S]+.
2-({5-[(2-Amino-1,3-thiazol-4-yl)methyl]-1,3,4-
oxadiazol-2-yl}sulfanyl)-N-(2,3-dimethylphenyl)acet-
amide (VIId). Brown solid; Yield: 87%; mp: 241–
242°C; Mol. Formula: C16H17N5O2S2; Mol. Mass:
375 g mol–1; IR: 3352 (N–H stretching), 3050 (C–H
of aromatic ring), 2930 (–CH2 stretching), 1675 (C=O
stretching), 1575 (C=C stretching of aromatic ring),
4.04 (s, 2H, CH2-6); 13C NMR: 168.75 (C-2'), 165.69 (C-
5'), 164.71 (C-1''), 163.05 (C-2), 143.90 (C-4), 138.61 (C-
1'''), 128.70 (C-3''' and C-5'''), 123.64 (C-4'''), 119.15
(C-2''' and C-6'''), 103.13 (C-5), 36.67 (C-2''), 27.53
(C-6); EI MS: m/z 361 [M]+, 287 [C14H13N3O2S]+,
1
1520 (C=N stretching); H NMR: 10.21 (s, 1H, N–
H), 7.26 (br.d, J = 8.1 Hz, 1H, H-4'''), 7.06 (br.d, J =
8.1, 1H, H-5'''), 7.26 (br.d, J = 8.1 Hz, 1H, H-6'''),
6.99 (br.s, 2H, –NH2), 6.38 (s, 1H, H-5), 4.23 (br.s,
2H, CH2-2''), 4.03 (br.s, 2H, CH2-6), 2.18 (s, 3H,
248
[C11H10N3O2S]+, 228 [C7H8N4OS2]+, 221
[C10H9N2O2S]+, 194 [C9H10N2OS]+, 181 [C9H11NOS],
141 [C5H5N2OS]+, 114 [C4H6N2S]+, 91 [C7H7].
CH3-8'''), 2.16 (s, 3H, CH3-7'''); 13C NMR: 168.74 (C-2'),
165.66 (C-5'), 164.37 (C-1''), 163.03 (C-2), 143.90
(C-4), 138.34 (C-1'''), 136.41 (C-3'''), 131.41(C-4'''),
129.62 (C-5'''), 120.35 (C-2'''), 116.68 (C-6'''), 103.12
(C-5), 36.64 (C-2''), 27.52 (C-6), 19.57 (C-7'''), 18.74
(C-8'''); EI MS: m/z 375 [M]+, 301 [C15H15N3O2S]+,
2-({5-[(2-Amino-1,3-thiazol-4-yl)methyl]-1,3,4-
oxadiazol-2-yl}sulfanyl)-N-(3,4-dimethylphenyl)acet-
amide (VIIb). Dark brown gummy solid; Yield: 84%;
mp: 278–279°C; Mol. Formula: C16H17N5O2S2; Mol.
262 [C12H12N3O2S]+, 235 [C11H11N2O2S]+, 195
[C10H13NOS]+, 163 [C10H13NO]+, 141 [C5H5N2OS]+,
121 [C8H11N]+, 114 [C4H6N2S]+.
Mass: 375 g mol–1; IR: 3360 (N–H stretching), 3045
(C–H of aromatic ring), 2920 (–CH2 stretching),
1660 (C=O stretching), 1570 (C=C stretching of aro-
1
matic ring), 1545 (C=N stretching); H NMR: 10.21
2-({5-[(2-Amino-1,3-thiazol-4-yl)methyl]-1,3,4-
oxadiazol-2-yl}sulfanyl)-N-(3,5-dimethylphenyl)acet-
amide (VIIe). Light brown amorphous solid; Yield:
82%; mp: 297–298°C; Mol. Formula: C16H17N5O2S2;
(s, 1H, N–H), 7.34 (br.s, 1H, H-2'''), 7.26 (br.d, J =
8.1 Hz, 1H, H-6'''), 7.06 (br.d, J = 8.1, H-5'''), 6.99
(br.s, 2H, –NH2), 6.38 (s, 1H, H-5), 4.23 (br.s, 2H,
CH2-2''), 4.03 (br.s, 2H, CH2-6), 2.18 (s, 3H, CH3-
Mol. Mass: 375 g mol–1; IR: 3367 (N–H stretching),
3040 (C–H of aromatic ring), 2940 (‒CH2 stretch-
ing), 1665 (C=O stretching), 1570 (C=C stretching of
13
8'''), 2.16 (s, 3H, CH3-7'''); C NMR: 168.74 (C-2'),
165.66 (C-5'), 164.37 (C-1''), 163.03 (C-2), 143.90
(C-4), 138.34 (C-1'''), 136.41 (C-3'''), 131.41 (C-4'''),
129.62 (C-5'''), 120.35 (C-2'''), 116.68 (C-6'''), 103.12
(C-5), 36.64 (C-2''), 27.52 (C-6), 19.57 (C-7'''), 18.74
(C-8'''); EI MS: m/z 375 [M]+, 301 [[C15H15N3O2S]+,
1
aromatic ring), 1530 (C=N stretching); H NMR:
10.21 (s, 1H, N–H), 7.34 (br.s, 1H, H-2'''), 7.26 (br.d,
J = 8.1 Hz, 1H, H-6'''), 7.06 (d, J = 8.1, H-4'''), 6.99
(br.s, 2H, –NH2), 6.38 (s, 1H, H-5), 4.23 (br.s, 2H,
CH2-2''), 4.03 (br.s, 2H, CH2-6), 2.18 (s, 3H, CH3-8'''),
262 [C12H12N3O2S]+, 235 [C11H11N2O2S]+, 195
[C10H13NOS]+, 163 [C10H13NO]+, 141 [C5H5N2OS]+,
121 [C8H11N]+, 114 [C4H6N2S]+.
2.16 (s, 3H, CH3-7'''); 13C NMR: 168.75 (C-2'), 165.67
(C-5'), 164.39 (C-1''), 163.05 (C-2), 143.90 (C-4),
138.34 (C-1'''), 136.41 (C-3'''), 131.41 (C-4'''), 129.62
(C-5'''), 120.35 (C-2'''), 116.68 (C-6'''), 103.12 (C-5),
36.64 (C-2''), 27.52 (C-6), 19.57 (C-7'''), 18.74 (C-
8'''); EI MS: m/z 375 [M]+, 301 [[C15H15N3O2S]+, 262
2-({5-[(2-Amino-1,3-thiazol-4-yl)methyl]-1,3,4-
oxadiazol-2-yl}sulfanyl)-N-(2,5-dimethylphenyl)acet-
amide (VIIc). Dull white amorphous solid; Yield:
83%; mp: 207–208°C; Mol. Formula: C16H17N5O2S2;
[C12H12N3O2S]+,
235
[C11H11N2O2S]+,
195
Mol. Mass: 375 g mol–1; IR: 3340 (N–H stretching),
3060 (C–H of aromatic ring), 2915 (‒CH2 stretch-
ing), 1570 (C=C stretching of aromatic ring), 1520
[C10H13NOS]+, 163 [C10H13NO]+, 141 [C5H5N2OS]+,
121 [C8H11N]+, 114 [C4H6N2S]+.
1
(C=N stretching); H NMR: 10.37 (s, 1H, N–H),
2-({5-[(2-Amino-1,3-thiazol-4-yl)methyl]-1,3,4-
7.56 (br.d, J = 8.0 Hz, 2H, H-2''' and H-6'''), 7.32 oxadiazol-2-yl}sulfanyl)-N-phenylacetamide
(VIIf).
(br.t, J = 7.8 Hz, 2H, H-3''' and H-5'''), 7.07 (br.t, J = Brick brown amorphous solid; Yield: 87%; mp: 190–
7.2 Hz, 1H, H-4'''), 6.99 (s, 2H, –NH2), 6.39 (s, 1H, 191°C; Mol. Formula: C14H13N5O2S2; Mol. Mass:
H-5), 4.26 (s, 2H, CH2-2''), 4.04 (s, 2H, CH2-6); 13C 347 g mol–1; IR: 3350 (N–H stretching), 3052 (C–H
of aromatic ring), 2923 (–CH2 stretching), 1576 (C=C
NMR: 168.75 (C-2'), 165.69 (C-5'), 164.71 (C-1''),
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY Vol. 46 No. 4 2020