New 2-Iminoderivatives of 2,5-Dihydrofurans
11
2
-Imino-3-(N-methyl)carbamoyl-4,5,5-trimethyl-2,5-dihydrofuran (1b)
Was obtained from 3-hydroxy-3-methylbutan-2-one (1.02 g, 10 mmol)
and methyl amide of cyanoacetic acid (0.98 g, 10 mmol) in 93% yield,
ꢁ
m.p.: 96–97 C. Found, %: C 59.45; H 7.78, N 15.01, C H N O
9
(
14
2
2
1
182.22). Calculated, %: C 59.32, H 7.74, N 15.37. H NMR (DMSO-
d =CCl : 1=3) d : 1.48 (6H, s, 2CH ), 2.35 (3H, s, CH ), 2.82 (3H, d,
6
4
H
3
3
3
13
J ¼ 4.9, NCH ), 7.21(1H, br, ¼ NH), 9.88 (1H, br, NH). C NMR
3
(
DMSO-d =CCl : 1=3) d : 11.79 (CH ), 24.16 (2CH ), 41.64 (NCH ),
6 4 C 3 3 3
8
7.29 (C ), 118.25 (C ), 162.32, 166,29 and 170.86 (C , C and C ¼ O).
5
3
4
2
ꢂ1
IR, n , cm : 3340, 3160, 1680, 1640, 1620.
max
2
-Imino-3-(N-benzyl)carbamoyl-4,5,5-trimethyl-2,5-dihydrofuran (1c)
Was obtained from 3-hydroxy-3-methylbutan-2-one (1.02 g, 10 mmol) and
benzyl amide of cyanoacetic acid (0.98 g, 10 mmol) in 93% yield, m.p.: 66–
ꢁ
6
7 C. Found, %: C 69.65, H 6.98, N 10.55. C H N O (258.32). Calcu-
2
1
5
18
2
1
lated, %: C 69.74, H 7.02, N 10.84. H NMR (DMSO-d =CCl : 1=3) d :
6
4
H
3
1
7
.44 (6H, s, 2CH ), 2.39 (3H, s, CH ), 4.46 (2H, d, J ¼ 6.0, NCH ), 7.16 –
3
3
2
3
13
C
.30 (5H, m, C H ), 7.32 (1H, s, ¼ NH), 9.88 (1H, t, J ¼ 6.0, NH).
6 5
NMR (DMSO-d =CCl : 1=3) d : 11.81 (CH ), 24.16 (2CH ), 41.64
6
4
C
3
3
(
(
CH ), 87.64 (C ), 118.26 (C ), 126.28 (Carom4), 126.89 (Carom2,6), 127.78
), 160.41, 166,21 and 170.77 (C , C and
2
5
3
Carom3,5), 138.43 (C
arom1
ꢂ1
4
2
C ¼ O). IR, nmax, cm : 3300, 3160, 1680, 1640, 1620, 1600.
2
-Imino-3-carbamoyl-4-methyl-5,5-pentamethylene-2,5-dihydrofuran (1d)
Was obtained from 1-acetylcyclohexanol (1.42 g, 10 mmol) and amide of
ꢁ
cyanoacetic acid (0.84 g, 10 mmol) in 95% yield, m.p.: 220–221 C. Found,
%
: C 63.63, H 8.01, N 13.68. C H N O (208,26). Calculated, %: C
11 16 2 2
1
6
m), 1.47 (2H, m) and 1.58–1.82 (7H, m, C H ), 2.33 (3H, s, CH ), 7.11
3.44, H 7.74, N 13.45. H NMR (DMSO-d =CCl : 1=3) d : 1.27 (1H,
6 4 H
5
10
3
1
3
(
(
1H, br) and 8.86 (1H, br, NH ), 7.18 (1H, s, ¼ NH). C NMR
2
DMSO-d =CCl : 1=3) d : 12.08 (CH ), 21.22 (2 C, b-CH ), 23.96 (2 C,
6
4
C
3
2
c-CH ), 32.39 (2 C, a-CH ), 88.73 (C ), 119.12 (C ), 162.43, 166.44 and
2
2
5
2
ꢂ1
1
70.88 (C , C and C ¼ O). IR, nmax, cm : 3412, 3263, 1671, 1635, 1620.
4
2
2-Imino-3-(N-methyl)carbamoyl-4-methyl-5,5-pentamethylene-2,5-
dihydrofuran (1e)
Was obtained from 1-acetylcyclohexanol (1.42 g, 10mmol) and methyl
ꢁ
amide of cyanoacetic acid (0.98 g, 10 mmol) in 92% yield, m.p.: 96–97 C.