Synthesis of 5-Alkylidene and 5-Arylidenehydantoins
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(DMSO-d6): d 11.2 (s, 1H), 10 (s, 1H), 6.82 (s, 2H), 6.35 (s, 1H), 3.82 (s, 9H).
13C NMR (DMSO-d6): d 165.9, 156.2, 153.1, 138.4, 128.9, 127.6, 107.4, 60.5,
56.5. MS m/z: 278 (Mþ). Anal. calcd. for C13H14N2O5: C, 56.11; H, 5.07; N,
10.07. Found C, 56.20; H, 5.10; N, 10.01.
5-Cinnamalhydantoin (3h): Yield 84%. Mp: 285–2888C. IR (KBr): 3531,
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3448, 3224, 3029, 2755, 1755, 1707, 1647, 1613 cm21. H NMR (DMSO-
d6): d 11.2 (s, 1H), 9.97 (s, 1H), 7.50–7.26 (m, 6H), 6.93 (d, 1H), 6.23
(d, 1H). 13C NMR (DMSO-d6): d 165.1, 154.9, 137.1, 130, 129.2, 128.8,
127, 122.9, 109.2. MS m/z: 214 (Mþ). Anal. calcd. for C12H10N2O2: C,
67.28; H, 4.71; N, 13.08. Found C, 67.48; H, 4.75; N, 13.28.
5-(2-Methylcinnamal)hydantoin 3i: Yield 82%. Mp: 246–2488C. IR (KBr):
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3170, 3052, 2763, 1761, 1726, 1643 cm21. H NMR (DMSO-d6): d 11.2
(s, 1H), 9.98 (s,1H), 7.37–7.23 (m, 5H), 6.83 (s, 1H), 6.14 (s, 1H), 2.11
(s, 3H). 13C NMR (DMSO-d6): d 165.9, 155.8, 137.2, 135.3, 132.4, 129.5–
127.6, 127.6, 114.3, 17.3. MS m/z: 228 (Mþ). Anal. calcd. for C13H12N2O2:
C, 68.41; H, 5.30; N, 12.27. Found C, 68.56; H, 5.37; N, 12.43.
5-(n-Propylidene)hydantoin (3j): Yield 78%. Mp: 220–2228C. IR (KBr):
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3316, 3108, 2967, 2930, 2865, 1917, 1713, 1645 cm21. H NMR (DMSO-
d6): d 10 (s, 1H), 8.84 (s, 1H), 6.63 (s, 1H), 1.92–1.84 (m, 7H). 13C NMR
(DMSO-d6): d 174.7, 153.4, 122, 110.1, 65.4, 34.31, 25.92. MS m/z: 154
(Mþ). Anal. calcd. for C7H10N2O2: C, 54.54; H, 6.54; N, 18.17. Found C,
54.35; H, 6.58; N, 18.26.
5-(2,6,6-Trimethylhexa-1,5-dienylidene)hydantoin (3k): Yield 74%. Mp:
176–1788C. IR (KBr): 3855, 3185, 3050, 2969, 2927, 1767, 1713, 1647,
1624 cm21 1H NMR (DMSO-d6): d 11.1 (s, 1H), 9.98 (s, 1H), 6.15
.
(m, 2H), 5.07 (s, 1H), 2.11 (s, 3H), 1.83–1.63 (m, 4H), 1.58 (s, 6H). 13C
NMR (DMSO-d6): d 165.4, 154.9, 146.6, 131.7, 128.1, 123.9, 118.7, 105.8,
26.32, 25.86, 17.85, 17.28. MS m/z: 234 (Mþ). Anal. calcd. for
C13H18N2O2: C, 66.64; H, 7.74; N, 11.96. Found C, 66.76; H, 7.73; N, 12.01.
5-(3-Methoxy-4-hydroxybenzal)hydantoin (3l): Yield 82%. Mp: 270–
2718C. IR (KBr): 3627, 3513, 3355, 3083, 2718, 1742, 1713, 1657 cm21
.
1H NMR (DMSO-d6): d 11.1 (s, 1H), 9.97 (s, 1H), 9.40 (s, 1H), 7.09–7.03
(m, 2H), 6.76 (d, 1H), 6.34 (s, 1H), 3.82 (s, 3H). 13C NMR (DMSO-d6):
d 166, 156.1, 148.1, 148, 128.9, 125.8, 124.7, 123.9, 116.1, 56.20. MS m/z:
234 (Mþ). Anal. calcd. for C11H10N2O4: C, 56.41; H, 4.30; N, 11.96. Found
C, 56.54; H, 4.37; N, 12.02.
5-(6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-ylidene)hydantoin (3m): Yield
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76%. Mp: 218–2208C. IR (KBr): 3314, 2917, 1765, 1728, 1653 cm21. H
NMR (DMSO-d6): d 11.1 (s, 1H), 9.90 (s, 1H), 6.10 (s, 1H), 5.80 (s, 1H),