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Synthesis of 4-methylsulfanyl-2-oxo-5,6-dihydro-2H-benzo-
[h]chromene-3-carbonitriles (3): These were obtained by
stirring an equimolar mixture of methyl 2-cyano-3,3-
dimethylthioacrylate 1 (0.05 mol, 10.1 g) and 1-tetralone 2
(0.05 mol, 7.3 mL) in the presence of powdered KOH
(0.06 mol, 3.3 g) in DMSO (50 mL) for 5–6 h. The reaction
mixture was poured onto crushed ice with vigorous
stirring and the resulting precipitate was filtered, washed
with water, dried, and purified by crystallization from
methanol. Compound 3a: Yellow solid, yield: 94%; mp:
204–206 °C; IR (KBr): 2922, 2370, 2207, 1699, 1612, 1570,
1508, 1446, 1372, 1279, 1257, 1221, 1155, 1132, 1092, 1037,
1
968, 900, 784, 742 cmÀ1; H NMR: (300 MHz, CDCl3): d
2.77–2.83 (m, 2H, CH2), 2.88–2.96 (m, 2H, CH2), 2.98 (s,
3H, SCH3), 7.23–7.27 (m, 1H, ArH), 7.31–7.44 (m, 2H,