Month 2018
Nanocatalyzed Multicomponent Synthesis
chromatography (7:3) to afford the pure product. The
catalyst was separated, dried, washed with ethanol, and
reused for subsequent runs.
126.11, 126.46, 128.60, 128.79, 128.86, 128.90, 128.92,
130.66, 131.42, 134.43, 136.97, 139.15, 140.47, 151.11,
153.99, 159.16, 166.18. Anal. Calcd for C H N O S ;
26 16 6 2 2
5
-Amino-3-benzothiazol-2-yl-7-(2-chloro-phenyl)-2-phenyl-
C, 61.40; H, 3.17; N, 16.52; Found; C, 61.47; H, 3.22;
2
,3-dihydro-thiazolo[4,5-b]pyridine-6-carbonitrile (7a).
N, 16.58; MS (EI): m/z 508.08 [M+].
5-Amino-3-benzothiazol-2-yl-7-(2-nitro-phenyl)-2-phenyl-
2,3-dihydro-thiazolo[4,5-b]pyridine-6-carbonitrile (7e).
Yield: 92%; Brown; m.p. 180–182°C; FTIR (KBr,
ꢀ
1
cm ): 3364 (N-H Str., NH ), 3072 (C-H Str., Ar), 2992
2
(
C-H Str., thiazolidine), 2200 (-CN Str.), 1614 (C=C,
Yield: 80%; Mustard Brown; m.p. 232–234°C; FTIR
1
ꢀ1
Ar). H-NMR (400 MHz, CDCl ) δ (ppm): 4.89 (s, 1H,
(KBr, cm ): 3380 (N-H Str., NH
), 3078 (C-H Str., Ar),
2
3
NCHS), 7.19–7.65 (m, 13H, ArH), 8.18 (s, 2H, NH ).
2983 (C-H Str., thiazolidine), 2262 (-CN Str.), 1634
2
1
3
1
C-NMR (400 MHz, CDCl ) δ (ppm): 66.24, 83.51,
(C=C, Ar). H-NMR (400 MHz, CDCl
) δ (ppm): 4.91
3
3
1
1
1
1
15.48, 119.76, 121.15, 124.64, 126.13, 127.16, 128.20,
28.19, 128.64, 128.70, 128.89, 128.92, 130.55, 130.66,
30.72, 130.74, 132.34, 134.44, 134.75, 136.95, 151.10,
55.57, 159.45, 165.63. Anal. Calcd for C H ClN S ;
(s, 1H, NCHS), 7.19–8.15 (m, 13H, ArH), 8.68 (s, 2H,
13
NH ). C-NMR (400 MHz, CDCl ) δ (ppm): 67.42,
2 3
84.93, 114.68, 119.76, 120.85, 121.99, 124.28, 126.91,
126.46, 126.71, 128.16, 128.33, 129.39, 128.59, 128.60,
128.64, 128.92, 130.64, 130.72, 134.46, 136.94, 148.37,
151.30, 153.78, 159.00, 164.34. Anal. Calcd for
C H N O S ; C, 61.40; H, 3.17; N, 16.52; Found; C,
2
6
16
5 2
C, 62.70; H, 3.24; N, 14.06; Found; C, 62.73; H, 3.28;
N, 14.12; MS (EI): m/z 497.05 [M+], 499.05 [M + 2].
5
-Amino-3-benzothiazol-2-yl-7-(3,4-dimethoxy-phenyl)-2-
phenyl-2,3-dihydro-thiazolo[4,5-b]pyridine-6-carbonitrile
7b).
26 16 6 2 2
6
1.51; H, 3.19; N, 16.64; MS (EI): m/z 508.08 [M+].
(
(
2
(
Yield: 88%; Brick red; m.p. 174–176°C; FTIR
5
-Amino-3-benzothiazol-2-yl-7-furan-2-yl-2-phenyl-2,3-
ꢀ
1
KBr, cm ): 3335 (N-H Str., NH ), 3045 (C-H Str., Ar),
dihydro-thiazolo[4,5-b]pyridine-6-carbonitrile (7f). Yield:
2
ꢀ
1
983 (C-H Str., CH ), 2933 (C-H Str., thiazolidine), 2243
91%; Red Violet; m.p. 154–156°C; FTIR (KBr, cm ):
3
1
-CN Str.), 1627 (C=C, Ar). H-NMR (400 MHz, CDCl )
3353 (N-H Str., NH ), 3045 (C-H Str., Ar), 2936 (C-H
3
2
1
δ (ppm): 3.79 (s, 3H), 3.86 (s, 3H), 4.24 (s, 1H, NCHS),
6
(
Str., thiazolidine), 2227 (-CN Str.), 1608 (C=C, Ar). H-
1
3
.95–7.65 (m, 12H, ArH), 8.37 (s, 2H, NH2). C-NMR
NMR (400 MHz, CDCl ) δ (ppm): 4.63 (s, 1H, NCHS),
3
400 MHz, CDCl ) δ (ppm): 56.15, 56.88, 64.76, 84.34,
6.50 (dd, 1H, J = 3.4, 1.8 Hz), 6.78 (dd, 1H, J = 3.4,
3
1
1
1
1
11.02, 112.24, 115.05, 119.39, 121.26, 124.88, 127.56,
28.22, 128.44, 128.60, 128.83, 128.90, 128.92, 130.52,
30.77, 134.40, 136.91, 139.15, 148.31, 149.17, 152.75,
0
0
.9 Hz), 7.20–7.62 (m, 9H, ArH), 7.90 (dd, 1H, J = 1.8,
.9 Hz), 8.52 (s, 2H, NH2). C-NMR (400 MHz,
13
CDCl ) δ (ppm): 66.06, 83.01, 106.8, 111.36, 115.19,
119.76, 120.19, 125.12, 126.44, 128.10, 128.29, 128.60,
1
1
C H N OS ; C, 63.56; H, 3.33; N, 15.44; Found; C,
6
3
54.16, 159.80, 165.59. Anal. Calcd for C H N O S ;
2
8
21
5
2
2
C, 64.22; H, 4.04; N, 13.37; Found; C, 64.45; H, 4.20;
N, 13.43; MS (EI): m/z 523.11 [M+].
28.77, 128.92, 130.61, 130.73, 134.42, 136.93, 142.28,
52.10, 152.50, 154.85, 159.43, 166.67. Anal. Calcd for
5
-Amino-3-benzothiazol-2-yl-7-(4-hydroxy-phenyl)-2-
phenyl-2,3-dihydro-thiazolo[4,5-b]pyridine-6-carbonitrile
7c). Yield: 92%; Brown; m.p. 202–204°C; FTIR (KBr,
24
15
5
2
3.59; H, 3.38; N, 15.46; MS (EI): m/z 453.07 [M+].
(
5
-Amino-3-benzothiazol-2-yl-2-phenyl-7-thiophen-2-yl-2,3-
ꢀ
1
cm ): 3420 (OH Str.), 3358 (N-H Str., NH ), 3,066 (C-H
Str., Ar), 2922 (C-H Str., thiazolidine), 2228 (-CN Str.),
2
dihydro-thiazolo[4,5-b]pyridine-6-carbonitrile (7g).
Yield:
ꢀ1
9
3
3%; Red brown; m.p. 176–178°C; FTIR (KBr, cm ):
1
1
4
2
8
1
1
1
612 (C=C, Ar). H-NMR (400 MHz, CDCl ) δ (ppm):
.66 (s, 1H, NCHS), 6.95–7.65 (m, 13H, ArH), 8.45 (s,
H, NH2). C-NMR (400 MHz, CDCl ) δ (ppm): 66.52,
3.68, 115.24, 119.76, 121.17, 124.52, 126.66, 127.16,
28.21, 128.47, 128.54, 128.60, 128.84, 128.92, 130.55,
30.64, 130.72, 130.74, 132.34, 132.90, 134.46, 136.90,
50.14, 156.25, 159.12, 166.83. Anal. Calcd for
3
367 (N-H Str., NH ), 3088 (C-H Str., Ar), 2974 (C-H
2
Str., thiazolidine), 2218 (-CN Str.), 1626 (C=C, Ar).
13
1
3
H-NMR (400 MHz, CDCl ) δ (ppm): 4.68 (s, 1H,
3
NCHS), 7.06 (dd, 1H, J = 7.9, 5.9 Hz), 7.19–7.42 (m,
9
1
H, ArH), 7.47 (dd, 1H, J = 7.9, 1.2 Hz), 7.75 (dd,
13
H, J = 5.9, 1.2 Hz), 8.22 (s, 2H, NH2). C-NMR
(400 MHz, CDCl ) δ (ppm): 65.18, 83.77, 116.72,
3
C H N OS ; C, 65.12; H, 3.57; N, 14.60; Found; C,
2
6
17
5
2
119.76, 122.34, 124.06, 125.49, 125.97, 127.78,
65.16; H, 3.61; N, 14.65; MS (EI): m/z 479.09 [M+].
1
1
1
28.20, 128.22, 128.57, 128.60, 128.63, 128.92,
30.16, 130.72, 134.45, 136.75, 142.69, 150.09,
55.19, 159.69, 165.76. Anal. Calcd for C H N S ;
5
-Amino-3-benzothiazol-2-yl-7-(4-nitro-phenyl)-2-phenyl-
2
,3-dihydro-thiazolo[4,5-b]pyridine-6-carbonitrile (7d).
24 15 5 3
Yield: 85%; Dark Coffee; m.p. 212–214°C; FTIR (KBr,
cm ): 3385 (N-H Str., NH ), 3098 (C-H Str., Ar), 2967
C, 61.38; H, 3.22; N, 14.91; Found; C, 61.43; H, 3.26;
N, 14.98; MS (EI): m/z 469.05 [M+].
ꢀ
1
2
(C-H Str., thiazolidine), 2249 (-CN Str.), 1627 (C=C,
5
-Amino-3-benzothiazol-2-yl-7-(1H-indol-3-yl)-2-phenyl-2,3-
1
Ar). H-NMR (400 MHz, CDCl ) δ (ppm): 4.95 (s, 1H,
dihydro-thiazolo[4,5-b]pyridine-6-carbonitrile (7h).
89%; Brown; m.p. 243–245°C; FTIR (KBr, cm ): 3410,
3285 (N-H Str., in NH indole, NH ), 3040 (C-H Str., Ar),
Yield:
3
ꢀ
1
NCHS), 7.19–8.24 (m, 13H, ArH), 8.63 (s, 2H, NH ).
2
1
3
C-NMR (400 MHz, CDCl ) δ (ppm): 65.83, 86.22,
3
2
116.56, 117.29, 118.14, 119.76, 121.11, 124.36, 125.45,
2925 (C-H Str., thiazolidine), 2232 (-CN Str.), 1665
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet