552 Letters in Organic Chemistry, 2011, Vol. 8, No. 8
Kuarm et al.
(CDCl3) ꢀ=14.5, 19.5, 19.7, 37.2, 61.8, 112.9, 155.8, 164.2,
168.9; ESI-MS; m/z =263 (100) [M+1]+. Anal. Calcd for
C9H14N2O2Se: C, 41.39; H, 5.40; N, 10.73. Found: C, 41.25;
H, 5.25; N, 10.93.
for C12H12N2O2S: C, 58.05; H, 4.87; N, 11.28; S, 12.91.
Found: C, 58.17; H, 5.07; N, 11.45; S, 12.75.
Ethyl 2-amino-4-phenyl selenazole-5-carboxylate (Table 1,
entry-10)
Benzyl 2-amino-4-isopropylthiazole-5-carboxylate (Table 1,
entry-5)
White solid.
Mp 178-180 oC. IR (KBr): 3404, 3274, 1648, 1513, 1292,
White solid.
1
1071 cm-1. HNMR (CDCl3, 300 MHz): ꢀ= 1.15(t, J = 7.41
Mp 166-168 oC. IR (KBr): 3380, 3316, 3161, 2957, 1692,
1645, 1518, 1470, 1306, 1264, 1193, 1087 cm-1.1HNMR
(CDCl3, 300 MHz): ꢀ= 1.17(d, J = 7.53Hz. 6H), 3.85 (sept, J
= 7.53 Hz, 1H), 5.21 (s, 2H), 5.51 (br s, 2H), 7.25-7.40 (m,
5H); 13CNMR (CDCl3) ꢀ=23.1, 23.2, 32.4, 68.4, 115.7,
127.2, 127.3, 127.7, 129.0, 129.1, 141.5, 150.4, 166.4, 169.3;
ESI-MS; m/z = 277 (100) [M+1] +. Anal. Calcd for
C14H16N2O2S: C, 60.85; H, 5.84; N, 10.14; S, 11.60. Found:
C, 60.73; H, 5.98; N, 10.29; S, 11.48.
Hz. 3H), 2.95 (br s, 2H), 4.05 (q, J = 7.41 Hz, 2H), 7.20-
7.30(m, 2H), 7.50-7.60 (m, 3H); 13CNMR (CDCl3) ꢀ=14.3,
61.9, 115.0, 126.4, 126.5, 128.0, 128.5, 128.6, 136.7, 152.8,
165.4, 169.0; ESI-MS; m/z = 297 (100) [M+1]+. Anal. Calcd
for C12H12N2O2Se: C, 48.82; H, 4.10; N, 9.49. Found: C,
48.95; H, 4.27; N, 9.32.
CONCLUSIONS
In conclusion, we have developed an efficient method for
the synthesis of 2-amino thiazole and selenazole-5-
carboxylates in good yields with high purity under Solvent
free conditions. The notable factors of this reaction are an
extremely simple experimental procedure, mild reaction
conditions, environmentally friendly synthesis with no prod-
uct wastes or toxic solvents, and a reusable catalyst.
Benzyl 2-amino-4-isopropylselenazole-5-carboxylate (Table
1, entry-6)
White solid.
Mp 176-178 oC. IR (KBr): 3385, 3285, 3135, 2962, 2926,
1
2860, 1664, 1633, 1501, cm-1. HNMR (CDCl3, 300 MHz):
ꢀ= 1.17(d, J = 7.64Hz. 6H), 3.90 (sept, J =7.64, 1H), 5.20 (s,
2H), 5.65 (brs, 2H).7.25-7.40 (m, 5H); 13CNMR (CDCl3) ꢀ=
19.1, 19.3, 37.2, 68.6, 114.9, 127.3, 127.5, 127.8, 129.1,
129.3, 141.8, 153.4, 165.8, 169.0; ESI-MS; m/z = 325 (100)
[M+1]+. Anal. Calcd for C14H16N2O2S: C, 52.02; H, 4.99; N,
8.67. Found: C, 52.24; H, 5.12; N, 8.79.
ACKNOWLEDGMENTS
The author (B.S.K) is grateful to Council of Scientific
and Industrial Research (CSIR), New Delhi, Republic of
India for providing financial support in the form of CSIR-
Senior Research Fellowship (SRF)
Methyl 2-amino-4-4-tert-butylthiazole-5-carboxylate (Table
1, entry-7)
White solid.
REFERENCES
Mp 161-163 oC. IR (KBr): 3442, 3285, 1691, 1504, 1256,
1085 cm-1.1HNMR (CDCl3, 300 MHz): ꢀ= 1.40(s, 9H),
3.75(s, 3H), 5.50(br s, 2H); 13CNMR (CDCl3) ꢀ=31.3, 31.4,
31.6, 31.9, 59.5, 115.9, 151.4, 166.5, 169.5; ESI-MS; m/z =
215 (100) [M+1]+. Anal. Calcd for C9H14N2O2S: C, 50.45; H,
6.59; N, 13.07; S, 14.96. Found: C, 50.26; H, 6.37; N, 13.19;
S, 15.16.
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Methyl 2-amino-4-tert-butylselenazole-5-carboxylate (Ta-
ble 1, entry-8)
White solid.
Mp 146-148 oC. IR (KBr): 3403, 3308, 3156, 2956, 1687,
1642, 1468 cm-1.1HNMR (CDCl3, 300 MHz): ꢀ = 1.40(s,
9H), 3.70(s, 3H), 7.30 (brs, 2H); 13CNMR (CDCl3) ꢀ=28.4,
28.5, 28.6, 44.9, 62.0, 114.9, 152.4, 165.9, 169.5; ESI-MS;
m/z = 263 (100) [M+1]+. Anal. Calcd for C9H14N2O2Se: C,
41.39; H, 5.40; N, 10.73. Found: C, 41.54; H, 5.65; N, 10.59.
[4]
[5]
Bell, F. W.; Cantrell, A. S.; Hoberg, M.; Jaskunas, S. R.; Johans-
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Badorc, A.; Borders, M. F.; Cointet, P. D.; Savi, P.; Bernat, A.;
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Ethyl 2-amino-4-phenylthiazole-5-carboxylate (Table 1,
entry-9)
[7]
[8]
Rudolph, J.; Theis, H.; Hanke, R.; Endermann, R.; Johannsen, L.;
Geschke, F. U. J. Med. Chem., 2001, 44, 619.
White solid.
Mp 170-172 oC. IR (KBr): 3394, 3280, 1658, 1515, 1302,
1169, 1087 cm-1. 1HNMR (CDCl3, 300 MHz): ꢀ= 1.25 (t, J =
7.32 Hz, 3H), 4.18 (q, J = 7.32 Hz, 2H), 5.59 (brs, 2H), 7.30-
7.40(m, 3H), 7.60-7.70(m, 2H); 13CNMR (CDCl3) ꢀ=14.1,
61.4, 115.4, 127.4, 127.5, 128.7, 129.4, 129.5, 133.2, 153.9,
166.4, 169.7; ESI-MS; m/z = 249 (100) [M+1]+. Anal. Calcd
(a) Kim, K. S.; Kimball, S. D.; Misra, R. N.; Rawlins, D. B.; Hunt,
J. T.; Xiao, H. Y.; Lu, S.; Qian, L.; Han, W. C.; Shan, W.; Mitt, T.;
Cai, Z. W.; Poss, M. A.; Zhu, H.; Sack, J. S.; Tokarski, J. S.;
Chang, C. Y.; Pavletich, N.; Kamath, A.; Humphreys, W. G.;
Marathe, P.; Bursuker, I.; Kellar, K. A.; Roongta, U.; Batorsky, R.;
Mulheron, J. G.; Bol, D.; Fairchild, C. R.; Lee, F. Y.; Webster, K.
R. J. Med. Chem. 2002, 45, 3905; (b) Misra, R. N.; Xiao, H. Y.;