NMR (CDCl3, 125 MHz) δ 167.2, 151.6. 137.7, 132.2,
129.4, 126.1, 102.3, 21.4; GC-MS (EI): m/z 190 (M+).
4-(4-Nitrophenyl)thiazol-2-amine (3ka);[17] Chemical
Formula: C9H7N3O2S; Appearance: Yellow powder; Yield:
40 mg (36 %); MP: 284-286 oC (lit. 285-286 oC)[17]; FT-IR
(neat): 3394, 3302, 3145, 3114, 1638, 1592, 1536, 1410,
1317, 1036, 1H NMR (DMSO-d6, 400 MHz) δ 8.23 (d, J =
8.0 Hz, 2H), 8.04 (d, J = 8.0 Hz, 2H), 7.40 (s, 1H), 7.25 (s,
2H); 13C NMR (DMSO-d6, 100 MHz) δ 168.6, 147.6,
146.0, 140.7, 126.3, 124.0, 106.6; GC-MS (EI): m/z 222
(M+H+).
4-(m-Tolyl)thiazol-2-amine (3ca);[17] Chemical Formula:
C10H10N2S; oAppearance: White Solid; Yield: 39 mg (41%);
o
MP: 84-86 C (lit. 88-91 C)[17]; H NMR (DMSO-d6, 500
MHz) δ 8.71 (bs, 2H), 7.55 (s, 1H), 7.51 (d, J = 10.0 Hz,
1H), 7.29 (t, J = 7.5 Hz, 1H), 7.17 (d, J = 7.5 Hz, 1H), 7.13
(s, 1H), 2.29 (s, 3H); 13C NMR (DMSO-d6, 125 MHz) δ
169.2, 139.6, 137.4, 128.9, 128.6, 128.0, 125.3, 121.9,
101.3, 20.1; GC-MS (EI): m/z 190 (M+).
4-(4-(Methylsulfonyl)phenyl)thiazol-2-amine
(3la);[21]
Chemical Formula: C10H10N2O2S2; Appearanoce: White
powder; Yield: 65 mg (51 %); MP: 225-227 C; FT-IR
(neat): 3417, 3278, 3108, 1646, 1532, 1280, 1035, 1H
NMR (DMSO-d6, 400 MHz) δ 8.04 (d, J = 8.0 Hz, 2H),
7.91 (d, J = 8.0 Hz, 2H), 7.30 (s, 1H), 7.18 (s, 2H), 3.22 (s,
3H); 13C NMR (DMSO-d6, 100 MHz) δ 168.5, 148.2,
139.4, 138.8, 127.4, 126.0, 105.2, 43.6; MS-MS (EI): m/z
255 (M+H+).
4-(4-Chlorophenyl)thiazol-2-amine (3da);[17] Chemical
Formula: C9H7ClN2S; Appearance: White Solid; Yield: 64
o
o
mg (61%); MP: 165-167 C (lit. 161-162 C)[17]; FT-IR
(neat): 3435, 3279, 3108, 2757, 1631, 1532, 1327, 1036,
1H NMR (CDCl3, 500 MHz) δ 7.71 (d, J = 8.5 Hz, 2H),
7.34 (d, J = 10.0 Hz, 2H), 6.71 (s, 1H), 5.05 (s, 2H); 13C
NMR (CDCl3, 125 MHz) δ 167.4, 150.4, 133.6, 133.3,
128.9, 127.4, 103.4; GC-MS (EI): m/z 210 (M+).
4-(Furan-2-yl)thiazol-2-amine
(3ma);[22]
Chemical
4-(3-Chlorophenyl)thiazol-2-amine (3ea);[18] Chemical
Formula: C7H6N2OS; Appearance: Whitoe Solid; 1Yield: 20
o
mg (24%); MP: 112-114 C (lit. 115 C) [23]; H NMR
Formula: C9H7ClN2S; Appearance: White Solid; Yield: 58
o
o
mg (55 %); MP: 128-130 C (lit. 126-128 C)[18]; FT-IR
(neat): 3310, 3127, 1632, 1517, 1337, 1050, 1H NMR
(CDCl3, 500 MHz) δ 7.69 (s, 1H), 7.56 (d, J = 7.5 Hz, 1H),
7.23-7.17 (m, 2H), 6.66 (s, 1H), 5.20 (s, 2H); 13C NMR
(CDCl3, 125 MHz) δ 167.6, 150.0, 136.5, 134.7, 130.0,
127.8, 126.3, 124.1, 104.0; GC-MS (EI): m/z 210 (M+).
(CDCl3, 500 MHz) δ 7.39 (s, 1H), 6.69 (s, 1H), 6.62 (d, J
= 3.5 Hz, 1H), 6.44 (m, 1H), 5.03 (s, 2H); 13C NMR
(CDCl3, 125 MHz) δ 167.6, 150.4, 143.0, 142.0, 111.5,
106.5, 102.5; GC-MS (EI): m/z 166 (M+).
N,4-Diphenylthiazol-2-amine
(3ab);[24]
Chemical
Formula: C15H12N2S; Appearance: Slightly yellow Solid;
Yield: 20 mg (16 %); MP: 138-140 oC (lit. 133-135 oC)[23]
;
4-(2,4-Dichlorophenyl)thiazol-2-amine
(3fa);[19]
1H NMR (CDCl3, 500 MHz) δ 7.86 (d, J = 10.0 Hz, 2H),
7.42-7.30 (m, 8H), 7.08 (t, J = 7.0 Hz, 2H), 6.84 (s, 1H);
13C NMR (CDCl3, 125 MHz) δ 164.5, 151.5, 140.4, 134.7,
129.6, 128.8, 128.0, 126.2, 123.1, 118.3, 102.0; GC-MS
(EI): m/z 252 (M+).
Chemical Formula: C9H6Cl2N2S; Appearance: White
o
Solid; Yield: 61 mg (50%); MP: 157-159 C (lit. 161-163
oC)[19];1FT-IR (neat): 3451, 3275, 3107, 1630, 1536, 1335,
1025, H NMR (CDCl3, 500 MHz) δ 7.81 (d, J = 10.0 Hz,
1H), 7.45 (d, J = 2.0 Hz, 1H), 7.27 (dd, J1 = 8.5 Hz, J2 =
2.0 Hz, 1H), 7.08 (s, 1H), 5.02 (s, 2H) 13C NMR (CDCl3,
125 MHz) δ 166.2, 146.6, 133.7, 132.5, 132.2, 132.0,
130.3, 127.3, 108.8; GC-MS (EI): m/z 244 (M+).
Acknowledgements
4-(4-Iodophenyl)thiazol-2-amine (3ga);[18] Chemical
SMU and NAH thank the University Grants Commission (UGC-
New Delhi), India and the Council of Scientific and Industrial
Research (CSIR-New Delhi), India for Junior Research
Fellowships respectively. GA and NM thank the Kerala State
Council for Science Technology and Environment (KSCSTE),
Formula: C9H7IN2S; Appearance: Pale Yellow Solid;
Yield: 73 mg (48 %); MP: 167-169 oC (lit. 176-177 oC)[18]
;
FT-IR (neat): 3420, 3279, 3107, 1627, 1530, 1326, 1034,
1H NMR (CDCl3, 500 MHz) δ 7.70 (d, J = 8.5 Hz, 2H),
7.52 (d, J = 8.5 Hz, 2H), 6.74 (s, 1H), 5.01 (s, 2H); 13C
NMR (CDCl3, 125 MHz) δ 167.4, 150.4, 137.8, 134.2,
127.9, 103.6, 93.3; GC-MS (EI): m/z 302 (M+).
Trivandrum, India for
a
research grant (Order No.
341/2013/KSCSTE dated 15.03.2013) and a research fellowship
respectively. The authors are also thankful to EVONIK
Industries, Germany for financial support (ECRP 2016 dated
6.10.2016). We also thank the Sophisticated Analytical
Instrument Facility (SAIF) Mahatma Gandhi University,
Kottayam for MS-MS analysis.
4-(4-Bromophenyl)thiazol-2-amine (3ha);[18] Chemical
Formula: C9H7BrN2S; Appearance: Pale Yellow Solid;
o
o
Yield: 61 mg (48%); MP: 184-186 C (lit. 179-181 C)[18]
;
FT-IR (neat): 3426, 3279, 3109, 2757, 1634, 1531, 1334,
1
1035, H NMR (CDCl3, 500 MHz) δ 7.65 (d, J = 8.5 Hz,
2H), 7.49 (d, J = 8.0 Hz, 2H), 6.73 (s, 1H), 5.02 (s, 2H) 13
C
References
NMR (CDCl3, 125 MHz) δ 167.4, 150.4, 133.8, 131.8,
127.7, 121.8, 103.5; GC-MS (EI): m/z 254 (M+).
[1] P. D. R. Guay, Clin Ther. 2002, 24, 473–489.
4-(4-Fluorophenyl)thiazol-2-amine (3ia);[18] Chemical
[2]. L. Laine, A. J. Kivitz, A. E. Bello, A. Y. Grahn, A. Y
Formula: C9H7FN2S; Appearance: White Solid; Yield: 53
o
o
mg (55%); MP: 100-102 C (lit. 103-104 C)[18]; FT-IR
(neat): 3469, 3306, 3126, 2767, 1639, 1533, 1338, 1037,
1H NMR (CDCl3, 500 MHz) δ 7.76-7.73 (m, 2H), 7.08-
7.04 (m, 2H), 6.65 (s, 1H), 5.02 (s, 2H); 13C NMR (CDCl3,
125 MHz) δ 167.3, 163.6, 161.6, 150.5, 140.1, 131.1 (2
peaks), 127.9, 127.8, 115.7, 115.5, 102.6 (2 peaks); GC-
MS (EI): m/z 194 (M+).
Schiff, A. S. Taha, Am. J. Gastro. 2012, 107, 379–386.
[3]. C. Borelli, M. Schaller, M. Niewerth, K. Nocker, B.
Baasner, D. Berg, R. Tiemann, K. Tietjen, B. Fugmann,
S. Lang-Fugmann, H. C. Korting, Chemotherapy 2008,
54, 245–259.
[4]. J. Pastre, D. L. Browne, M. O’Brien, S. V. Ley, Org
Proc Res Dev. 2013, 17, 1183-1191.
4-(3-(Trifluoromethyl)phenyl)thiazol-2-amine (3ja);[20]
Chemical Formula: C10H7F3N2S; Apopearance: White Solid;
1
Yield: 40 mg (33%); MP: 103-105 C; H NMR (DMSO-
[5]. C. De Battista, H. B. Solvason, J. A. Breen, A. F.
Schatzberg, J. Clin. Psychopharmacol. 2000, 20, 274–
275.
d6, 500 MHz) δ 8.13 (s, 1H), 8.09 (bs, 1H), 7.59 (bs, 2H),
7.25 (bs, 1H), 7.18 (s, 2H); 13C NMR (DMSO-d6, 125
MHz) δ 167.7, 147.2, 134.9, 130.2, 130.1, 130.0, 129.7,
129.6, 129.5, 128.0, 125.8, 124.0 (2 peaks), 123.7, 122.4 (2
peaks), 121.5; GC-MS (EI): m/z 244 (M+).
[6]. R. M. Dodson, L. C. King, J. Am. Chem. Soc. 1946,
68, 871–871.
5
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