Cyclopropane carbohydrazide derivatives
3
144 (NH stretching), 1656 (C=O stretching), 1601 (* 19.2), 18.5 (* 18.1), 14.2 (* 13.1) (Cyclopropane);
1
+
(
1
1
C=N stretching); H NMR (400 MHz, DMSO-d ) δ ESI-MS, m/z: 256.2 [M+H] .
6
1.30 (* 11.10, s, 1H, –CO-NH-N-), 8.26 (* 8.17, s,
H, -N=CH-), 7.49 (d, J = 0.8 Hz, 1H, Ar-H), 6.36
ꢁ
(
E)-2-(furan-2-yl)-N -(pyridin-2-ylmethylene)cyclopro-
(
6
3
dd, J = 2.0, 3.2 Hz, 1H, Ar-H), 6.26 (s, 1H, Ar-H),
panecarbohydrazide (5k): Off-white solid; Yield: 45
.24 (s, 1H, Ar-H), 6.20 (d, J = 3.1 Hz, 1H, Ar-H),
o
−1
mg, 29%; M.p. 150-156 C; IR (KBr): νmax/cm 3183
.80 (s, 3H, -OCH ), 3.79 (s, 3H, -OCH ), 3.70 (s, 3H,
3
3
(
NH stretching), 1661 (C=O stretching), 1577 (C=N
-OCH ), 3.01-2.97 (* 2.35-2.31, m, 1H, cyc-CH-Ar),
3
1
stretching); H NMR (400 MHz, DMSO-d ) δ 11.88
6
2
.39-2.36 (* 1.94-1.92, m, 1H, cyc-CH-CO-), 1.42-1.25
13
(* 11.77, brs, 1H, –CO-NH-N-), 8.59-8.56 (t, J = 5.0
(m, 2H, cyc-CH -); C NMR (100 MHz, DMSO-d6)
2
Hz, 1H, Ar-H), 8.15 (* 8.08, s, 1H, -N=CH-), 7.90-
δ 171.9 (C=O), 166.2, 162 (* 161.8), 159.7 (* 159.7)
7
1
.81 (m, 2H, Ar-H), 7.51 (s, 1H, Ar-H), 7.40-7.35 (m,
H, Ar-H), 6.37 (d, J = 1.9 Hz, 1H, Ar-H), 6.26-6.24
(
Ar-C), 154 (* 153.8) (C=N), 141.7 (* 141.3), 138.3,
1
5
1
10.5, 105, 104.7 (* 104.0), 91.11 (* 91.10) (Ar-C),
(
dd, J = 3.1, 6.2 Hz, 1H, Ar-H), 2.93-2.91 (* 2.41-
5.8, 55.7, 55.3 (OCH ), 22.3 (* 19.5), 18.3 (* 17.4),
3
+
2.39, m, 1H, cyc-CH-Ar), 2.49 (* 1.99-1.97, m, 1H,
3.7 (* 12.7); ESI-MS, m/z: 345.2 [M-H] .
13
cyc-CH-CO-), 1.45-1.34 (m, 2H, cyc-CH -); C NMR
2
(
1
1
(
(
100 MHz, DMSO-d ) δ 172.4 (C=O), 167.3 (Ar-C),
6
ꢁ
(
E)-2-(furan-2-yl)-N -(4-(methylthio)benzylidene)
53.5 (* 153.1) (C=N), 149.4, 146.2, 141.4 (* 141.3),
cyclopropanecarbohydrazide (5i): Off-white solid;
M.p. 148-152 C; Yield: 73 mg; 57%; IR (KBr):
36.7, 124.2 (* 124.0), 119.7 (* 119.5), 110.6, 105.2
◦
Ar-C), 22.4 (* 19.2), 18.5 (* 18.0), 14.2 (* 13.1)
−1
νmax/cm 3250 (NH stretching), 1653 (C=O stretching),
+
Cyclopropane); ESI-MS, m/z: 256.2 [M+H] .
1
1
599 (C=N stretching); H NMR (400 MHz, DMSO-
d ) δ 11.62 (* 11.47, s, 1H, –CO-NH-N-), 8.0 (* 7.98,
6
ꢁ
s, 1H, -N=CH-), 7.61-7.59 (d, J = 8.5 Hz, 1H, Ar-H), (E)-2-(furan-2-yl)-N -((6-methylpyridin-3-yl)methylene)
7
.56-7.54 (d, J = 8.5 Hz, 1H, Ar-H), 7.51-7.49 (dd, cyclopropanecarbohydrazide (5l): White solid; Yield:
◦ −1
J = 1.0,4.1, Hz, 1H, Ar-H), 7.30-7.26 (t, J = 8.5 Hz, 58 mg, 51%; M.p. 198-202 C; IR (KBr): νmax/cm
2
6
(
H, Ar-H), 6.37-6.36 (dd, J = 2.0, 4.1 Hz, 1H, Ar-H), 3177 (NH stretching), 1688 (C=O stretching), 1605
1
.24-6.21 (dd, J = 3.1, 7.0 Hz, 1H, Ar-H), 2.90-2.87 (C=N stretching); H NMR (400 MHz, DMSO-d ) δ
6
* 2.37-2.33, m, 1H, cyc-CH-Ar), 2.52 (s, 3H, -SCH ), 11.76 (* 11.60, s, 1H, –CO-NH-N-), 8.67 (* 8.62, d,
3
2
.46-2.42 (* 1.98-1.95, m, 1H, cyc-CH-CO-), 1.43-1.30 J = 1.7 Hz, 1H, Ar-H), 8.17 (* 8.04, s, 1H, -N=CH-),
13
(m, 2H, cyc-CH -); C NMR (100 MHz, DMSO- 7.98-7.92 (m, 1H, Ar-H), 7.50 (s, 1H, Ar-H), 7.32-7.27
2
d ) δ 172.6 (C=O), 167.4 (Ar-C), 154.2 (* 154.1) (q, J = 8.4 Hz, 1H, Ar-H), 6.38-6.36 (dd, J = 1.8, 3.0
6
(
1
1
(
[
C=N), 146, 143.5, 141.9 (* 141.8), 141.2 (* 140.9), Hz, 1H, Ar-H), 6.25-6.22 (dd, J = 3.2, 6.2 Hz, 1H,
31.1 (* 130), 127.8 (* 127.5), 126.2 (* 126.1), Ar-H), 2.93-2.90 (* 2.39-2.35, m, 1H, cyc-CH-Ar),
11.1, 105.6 (Ar-C), 22.9 (-SCH ), 19.8 (* 18.8), 14.7 2.49 (s, 3H, Ar-CH ), 2.38 (* 1.99-1.97, m, 1H, cyc-
3
3
13
* 14.5), 13.4 (Cyclopropane); ESI-MS, m/z: 301.23 CH), 1.44-1.32 (m, 2H, cyc-CH -): C NMR (100
2
+
M+H] .
MHz, DMSO-d ) 172.2 (C=O), 167-(Ar-C), 153.6
6
(
1
(
* 153.5) (C=N), 148 (* 147.8), 143.4, 141.4 (* 141.3),
33.5 (* 133.2), 127.3 (* 127.2), 123.2, 110.5, 105.1
ꢁ
(
E)-2-(furan-2-yl)-N -(pyridin-4-ylmethylene)cyclopro-
Ar-C), 23.9 (Ar-CH ), 22.3 (* 19.2), 18.4 (* 17.8),
3
panecarbohydrazide (5j): Yellow solid; M.p. 48-
5
(
stretching); H NMR (400 MHz, DMSO-d ) δ 11.94
(
1
4.1 (* 12.9)-(Cyclopropane); ESI-MS, m/z: 270.26
◦
−1
2 C; Yield; 50 mg, 46%; IR (KBr): νmax/cm 3196
+
[
M+H] .
NH stretching), 1667 (C=O stretching), 1598 (C=N
1
6
ꢁ
* 11.78, s, 1H, –CO-NH-N-), 8.67-8.58 (m, 2H, Ar-H), (E)-N -((1H-indol-5-yl)methylene)-2-(furan-2-yl)cyclo-
8
1
6
.14 (* 8.02, s, 1H, -N=CH-), 7.61-7.56 (dd, J = 5.0, propanecarbohydrazide (5m): Off-white solid; Yield:
◦
−1
6 Hz, 2H, Ar-H), 7.51 (d, J = 4.7 Hz, 1H, Ar-H), 65 mg, 52%; M.p. 260-264 C; IR (KBr): νmax/cm
.37 (s, 1H, Ar-H), 6.25-6.23 (dd, J = 2.6, 7.2 Hz, 1H, 3190 (NH stretching), 3141 (Indole-NH stretching),
1
Ar-H), 2.95-2.90 (* 2.42-2.38, m, 1H, cyc-CH-ArH), 1655 (C=O stretching), 1609 (C=N stretching); H
2
.49-2.46 (* 2.03-1.90, m, 1H, cyc-CH-Ar), 1.44-1.21 NMR (400 MHz, DMSO-d ) δ 11.81 (s, 1H, indole-
6
13
(m, 2H, cyc-CH -); C NMR (100 MHz, DMSO-d6) NH), 11.62 (* 11.45, s, 1H, –CO-NH-N-), 8.51 (* 8.47,
2
δ172.6 (C=O), 167.4 (Ar-C), 153.5, 153.4 (C=N), d, J = 1.9 Hz, 1H, -N=CH-), 8.27-8.15 (m, 2H, Ar-H),
50.17 (* 150.13), 143.5, 141.5 (* 141.4), 141.1 7.52-7.50 (dd, J = 0.8, 5.4Hz, 2H, Ar-H), 6.52-6.49
* 141.0), 120.8, (* 120.5), 110.6, 105.2 (Ar-C), 22.4 (m, 1H, Ar-H), 6.38-6.36 (dd, J = 3.0, 5.1, Hz, 2H,
1
(