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LETTER
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Acknowledgement
Authors thank Department of Science and Technology (DST), New
Delhi, for financial support and members of Sophisticated Analyti-
cal Instrumentation Facility (SAIF), CDRI, Lucknow, for providing
elemental analyses and spectroscopic data of synthesized com-
pounds.
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A mixture of 6-aryl-3-cyano-4-methylsulfanyl-2H-pyran-2-
ones (1, 1 mmol) and urea (2.3 mmol) was fused at 150 °C
for 5–15 min. After completion, the reaction was cooled to
r.t. and H2O was added (10 mL) to give the crude compound.
The pure compounds were isolated on silica gel column,
using CHCl3–hexane (1:1) as eluent.
(28) Spectroscopic and Elemental Analyses Data of Selected
Compounds.
Compound 2a: yellow solid; mp 136–138 °C. 1H NMR (200
MHz, CDCl3): d = 2.50 (s, 3 H, SCH3), 4.23 (br s, 2 H, NH2),
6.30 (s, 1 H, PyH), 6.90 (s, 1 H, PyH), 7.41–7.44 (m, 3 H,
ArH), 7.87–7.90 (m, 2 H, ArH). IR (KBr): 3430 cm–1 (NH2).
MS (FAB): 217 [M+ + 1]. Anal. Calcd for C12H12N2S: C,
66.63; H, 5.59; N, 12.95. Found: C, 66.69; H, 5.61; N, 12.83.
Compound 3a: CCDC No. 238556; white solid; mp
>250 °C. 1H NMR (200 MHz, DMSO-d6): d = 2.73 (s, 3 H,
SCH3), 6.61 (s, 1 H, CH), 7.56–7.59 (m, 3 H, ArH), 7.83–
7.87 (m, 2 H, ArH), 12.50 (br s, 1 H, NH). IR (KBr): 1645
(CO), 2214 (CN), 3444 cm–1 (NH). MS (FAB): 243 [M+ +
1]. Anal. Calcd for C13H10N2OS: C, 64.44; H, 4.16; N, 11.56.
Found: C, 64.66; H, 4.28; N, 11.62.
Compound 5c: white solid; mp 133-134 °C. 1H NMR (200
MHz, DMSO-d6): d = 2.44 (s, 3 H, CH3), 2.56 (s, 3 H,
SCH3), 6.12 (s, 1 H, CH), 6.47 (s, 1 H, CH), 7.31 (d, J = 8.0
Hz, 2 H, ArH), 7.62 (d, J = 8.0 Hz, 2 H, ArH), 11.50 (br s, 1
H, NH). IR (KBr): 1628 (CO), 3383 cm–1 (NH). MS (FAB):
232 [M+ + 1]. Anal. Calcd for C13H13NOS: C, 67.50; H, 5.66;
N, 6.06. Found: C, 67.62; H, 5.69; N, 6.18.
Synlett 2005, No. 4, 623–626 © Thieme Stuttgart · New York