1072
KULATHOORAN et al., Orient. J. Chem., Vol. 32(2), 1067-1073 (2016)
6.38 (s, 1H, furyl-H), 7.44-7.47 (m, 1H, Ar-H), 7.59- NH). 13C NMR (75.46 MHz, DMSO-d6, ä, ppm):
7.63 (m, 2H, Ar-H), 7.65 (b, 1H, NH), 7.72-7.74 (m, 175.90, 151.81, 150.71, 149.71, 146.80, 129.10,
1H, Ar-H), 8.02 (b, 1H, NH). 13C NMR (75.46 MHz, 127.34, 127.14, 125.03, 125.49, 124.21, 113.10,
DMSO-d6, d, ppm): 175.20, 151.81, 150.73, 149.74, 107.26, 66.61, 41.10, 14.71, 13.41. IR (KBr, v cm-1):
138.01, 131.94, 127.54, 127.30, 125.81, 125.01, 3444, 1594, 1478, 1367, 1324, 1064 cm-1. HR mass
119.14, 107.26, 106.42, 59.61, 41.41, 14.71, 13.41. Calcd. For C17H16F3N3OS: 367.1. Found: m/z 368.1
IR (KBr, v cm-1): 3450, 1579, 1483, 1422, 1306, (M+H)+.
1057cm-1. HR mass Calcd. for C17H16F3N3OS: 367.1.
Found: m/z 368.1 (M+H)+.
CONCLUSION
1-Thiocarbamoyl-3-(2,5-dimethylfuran-3-yl)-5-(3-
(trifluoromethyl)phenyl)-2-pyrazoline (4e)
In conclusion, we have developed a
simple, rapid and efficient green synthesis of
1H NMR (300 MHz, DMSO-d6, d, ppm): 1-thiocarbamoyl-3-(2,5-dimethylfuran-3-yl)-5-
2.22 (s, 3H, CH3), 2.44 (s, 3H, CH3), 3.07 (1H, dd, (fluoro/trifluoromethylphenyl)-2-pyrazolines from
pyrazoline HA, JAB: 17.7 Hz, JAX: 3.67 Hz), 3.91 (1H, commercially available acetylacetone in good yield
dd, pyrazoline HB, JAB: 17.9 Hz, JBX: 11.61 Hz), 5.98 under mild reaction condition. Microwave irradiation
(1H, dd, pyrazoline HX, JAx: 3.67 Hz, JBX: 11.61 Hz), solvent-free method shortened the reaction time and
6.40 (s, 1H, furyl-H), 7.39-7.46 (m, 2H, Ar-H), 7.55- improves yield of products (5-8 min. and 69-84%)
7.60 (m, 3H, Ar-H), 7.62 (b, 1H, NH), 7.99 (b, 1H, NH). than conventional method (5-6 hr and 54-64%).
13C NMR (75.46 MHz, DMSO-d6, ä, ppm): 175.90, The synthesized compounds were evaluated for
151.80, 150.73, 149.74, 143.81, 130.84, 130.13, their in vitro antimicrobial activity against various
128.94, 124.90, 125.81, 124.51, 113.14, 107.26, pathogenic bacterial and fungal strains. Compound
66.41, 41.41, 14.71, 13.41. IR (KBr, v cm-1): 3479, 4b showed valuable inhibitory activity against most
1569, 1482, 1348, 1320, 1073 cm-1. HR mass Calcd. of the microbial strains compared with standards.
for C17H16F3N3OS: 367.1. Found: m/z 368.1 (M+H)+.
ACKNOWLEDGMENTS
1-Thiocarbamoyl-3-(2,5-dimethylfuran-3-yl)-5-(4-
(trifluoromethyl)phenyl)-2-pyrazoline (4f)
The authors are gratefully acknowledged
1H NMR (300 MHz, DMSO-d6, d, ppm): to Hi-Tech research foundation, Tharangambadi,
2.22 (s, 3H, CH3), 2.43 (s, 3H, CH3), 3.07 (1H, dd, Tamilnadu, India for providing the financial and
pyrazoline HA, JAB: 17.6 Hz, JAX: 3.7 Hz), 3.91 (1H, laboratory facilities.Authors also thank Sophisticated
dd, pyrazoline HB, JAB: 17.7 Hz, JBX: 11.64 Hz), 5.95 Test & Instrumentation Centre, Cochin University of
(1H, dd, pyrazoline HX, JAx: 3.6 Hz, JBX: 11.64 Hz), Science and Technology, Cochin, Kerala, India for
6.39 (s, 1H, furyl-H), 7.32-7.34 (m, 2H, Ar-H), 7.62 spectral studies.
(b, 1H, NH), 7.68-7.70 (m, 2H, Ar-H), 7.99 (b, 1H,
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