Med Chem Res
13C-NMR (DMSO, 100 Hz): d 14.2, 19.5, 21.8, 26.9, 28.3,
41.8, 60.3, 129.0, 129.8, 132.8, 137.9, 157.2, 171.4. ESI–
MS: 391.1 ([M?2H]2?).
400 MHz): 0.60 (d, 1H, J = 4.78 Hz, Cpr–CH), 1.10 (s,
6H, 2CH3), 1.14 (t, 3H, J = 7.12 Hz, CH3), 1.41 (d, 1H,
J = 4.78 Hz, Cpr–CH), 4.10 (q, 2H, J = 7.12 Hz, CH2),
7.23 (s, 2H,), 7.28 (brs, 1H, NH), 8.33 (brs, 1H, NH), 9.41
(brs, 1H, NH). 13C-NMR (DMSO, 100 Hz): d 14.3, 18.3,
20.1, 28.7, 34.4, 42.9, 63.8, 129.88, 131.45, 135.72,
140.33, 159.1, 171.3. ESI–MS: 401.1 ([M?H]?).
Ethyl 1-(2-(4-bromophenylsulfonyl)hydrazinecarboxam-
ido)-2,2-dimethylcyclopropanecarboxylate (5d) Yield:
1
85 %. White solid. Mp: 118–120 °C. H-NMR (DMSO,
400 MHz): d 0.63 (d, 1H, J = 4.80 Hz, Cpr–CH), 1.08 (s,
6H, 2CH3), 1.11 (t, 3H, J = 7.20 Hz, CH3), 1.40 (d, 1H,
J = 4.80 Hz), 3.99 (q, 2H, J = 7.20 Hz, CH2), 6.32 (s, 1H,
NH), 7.84 (d, 2H, J = 8.40 Hz), 7.78 (d, 2H,
J = 8.40 Hz), 8.12 (s, 1H, NH), 9.54 (brs, 1H, NH). 13C-
NMR (DMSO, 100 Hz): d 14.8, 19.9, 21.4, 27.1, 28.5,
42.0, 61.3, 129.4, 129.6, 133.8, 137.4, 157.7, 171.9. ESI–
MS: 434.1 ([M?H]?).
Ethyl 1-(2-(2-chlorophenylsulfonyl)hydrazinecarboxam-
ido)-2,2-dimethylcyclopropanecarboxylate
(5i) Yield:
1
85 %. White solid. Mp: 124–126 °C. H-NMR (DMSO,
400 MHz): 0.60 (d, 1H, J = 4.72 Hz, Cpr–CH), 1.09 (s,
6H, 2CH3), 1.15 (t, 3H, J = 7.10 Hz, CH3), 1.40 (d, 1H,
J = 4.72 Hz, Cpr–CH), 4.12 (q, 2H, J = 7.10 Hz, CH2),
7.15–7.24 (m, 4H,), 7.26 (brs, 1H, NH), 8.30 (brs, 1H, NH),
9.52 (brs, 1H, NH). 13C-NMR (DMSO, 100 Hz): d 14.8,
18.1, 20.3, 28.8, 34.6, 42.3, 64.1, 126.38, 129.11, 129.56,
131.42, 132.45, 137.5, 158.7, 172.5. ESI–MS: 390.1
([M?H]?), 391.2 ([M?2H]2?).
Ethyl 1-(2-(4-fluorophenylsulfonyl)hydrazinecarboxamido)-
2,2-dimethylcyclopropanecarboxylate (5e) Yield: 85 %.
White solid. Mp: 123–125 °C. 1H-NMR (DMSO,
400 MHz): d 0.60 (d, 1H, J = 4.80 Hz, Cpr–CH), 1.06 (s,
6H, 2CH3), 1.10 (t, 3H, J = 7.40 Hz, CH3), 1.42 (d, 1H,
J = 4.80 Hz), 4.00 (q, 2H, J = 7.40 Hz, CH2), 6.24 (s, 1H,
NH), 7.74 (d, 2H, J = 8.20 Hz), 7.72 (d, 2H,
J = 8.20 Hz), 8.04 (s, 1H, NH), 9.32 (brs, 1H, NH). 13C-
NMR (DMSO, 100 Hz): d 14.2, 20.3, 21.2, 27.4, 28.4,
41.3, 61.7, 128.2, 129.8, 134.8, 138.1, 158.2, 172.0. ESI–
MS: 374.1([M?H]?).
Ethyl 1-(2-(2-fluorophenylsulfonyl)hydrazinecarboxamido)-
2,2-dimethylcyclopropanecarboxylate (5j) Yield: 88 %.
White solid. Mp: 127–129 °C. 1H-NMR (DMSO,
400 MHz): 0.61 (d, 1H, J = 4.72 Hz, Cpr–CH), 1.08 (s, 6H,
2CH3), 1.14 (t, 3H, J = 7.10 Hz, CH3), 1.42 (d, 1H,
J = 4.72 Hz, Cpr–CH), 4.10 (q, 2H, J = 7.10 Hz, CH2),
7.03–7.21 (m, 4H,), 7.22 (brs, 1H, NH), 8.42 (brs, 1H, NH),
9.47 (brs, 1H, NH). 13C-NMR (DMSO, 100 Hz): d 12.6,
18.3, 20.1, 28.7, 34.5, 42.7, 64.4, 126.48, 130.12, 130.56,
132.52, 138.2, 158.2, 166.35, 172.8. ESI–MS: 374.3
([M?H]?).
Ethyl 1-(2-(4-methoxyphenylsulfonyl)hydrazinecarboxam-
ido)-2,2-dimethylcyclopropanecarboxylate
(5f) Yield:
1
80 %. White solid. Mp: 122–124 °C. H-NMR (DMSO,
400 MHz): d 0.63 (d, 1H, J = 4.60 Hz, Cpr–CH), 1.09 (s,
6H, 2CH3), 1.12 (t, 3H, J = 7.40 Hz, CH3), 1.42 (d, 1H,
J = 4.60 Hz, Cpr–CH), 3.83(s, 3H, OCH3), 4.00 (q, 2H,
J = 7.40 Hz, CH2), 6.74 (s, 1H, NH), 7.10 (d, 2H,
J = 8.00 Hz), 7.70 (d, 2H, J = 8.00 Hz), 8.08 (s, 1H, NH),
9.35 (brs, 1H, NH). 13C-NMR (DMSO, 100 Hz): d 14.1,
20.6, 21.8, 28.3, 29.4, 42.3, 62.4, 127.1, 130.4, 132.9,
139.2, 158.7, 171.8. ESI–MS: 386.1 ([M?H]?).
Ethyl 1-(2-(3,5-dichlorophenylsulfonyl)hydrazinecarbox-
amido)-2,2-dimethylcyclopropanecarboxylate (5k) Yield:
1
85 %. White solid. Mp: 127–129 °C. H-NMR (DMSO,
400 MHz): 0.60 (d, 1H, J = 4.68 Hz, Cpr–CH), 1.11 (s,
6H, 2CH3), 1.12 (t, 3H, J = 7.12 Hz, CH3), 1.42 (d, 1H,
J = 4.68 Hz, Cpr–CH), 4.11 (q, 2H, J = 7.12 Hz, CH2),
7.03–7.21 (m, 3H), 7.27 (brs, 1H, NH), 8.53 (brs, 1H, NH),
9.62 (brs, 1H, NH). 13C-NMR (DMSO, 100 Hz): d 15.1,
20.2, 21.3, 26.5, 28.6, 42.3, 62.2, 117.4, 122.4, 136.5,
140.7, 158.6, 172.0. ESI–MS: 424.0 ([M?H]?), 425.1
([M?2H]2?).
Ethyl 1-(2-(mesitylphenylsulfonyl)hydrazinecarboxamido)-
2,2-dimethylcyclopropanecarboxylate (5g) Yield: 80 %.
White solid. Mp: 138–140 °C. 1H-NMR (DMSO,
400 MHz): 0.62 (d, 1H, J = 4.82 Hz, Cpr–CH), 1.10 (s,
6H, 2CH3), 1.14 (t, 3H, J = 7.12 Hz, CH3), 1.41 (d, 1H,
J = 4.82 Hz, Cpr–CH), 2.35 (s, 3H, CH3), 2.58 (s, 6H,
2CH3), 4.10 (q, 2H, J = 7.12 Hz, CH2), 7.23 (s, 2H,), 7.28
(brs, 1H, NH), 8.33 (brs, 1H, NH), 9.41 (brs, 1H, NH). 13C-
NMR (DMSO, 100 Hz): d 14.0, 18.3, 20.1, 28.7, 34.4,
42.9, 63.8, 129.88, 131.45, 135.72, 140.33, 159.1, 171.3.
ESI–MS: 398.2 [M?H]?.
Ethyl 2,2-dimethyl-1-(2-(2-(thiophen-2-ylsulfonyl)hydrazinecar-
boxamido)cyclopropanecarboxylate (5l) Yield: 80 %. White
solid. Mp: 110–112 °C. 1H-NMR (DMSO, 400 MHz): 0.62
(d, 1H, J = 4.62 Hz, Cpr–CH), 1.12 (s, 6H, 2CH3), 1.13 (t,
3H, J = 7.12 Hz, CH3), 1.44 (d, 1H, J = 4.62 Hz, Cpr–
CH), 4.13 (q, 2H, J = 7.12 Hz, CH2), 7.15–7.17 (m, 1H),
7.22 (brs, 1H, NH), 7.78–7.80 (m, 2H), 8.44 (brs, 1H, NH),
9.68 (brs, 1H, NH). 13C-NMR (DMSO, 100 Hz): d 14.9,
19.5, 20.6, 28.2, 29.5, 42.5, 62.8, 111.3, 143.8, 150.2, 150.8,
159.3, 171.6. ESI–MS: 362.1 ([M?H]?).
Ethyl-2,2-dimethyl-1-(2-(4-nitrophenylsulfonyl)hydrazinec
arboxamido)cyclopropanecarboxylate (5h) Yield: 82 %.
White solid. Mp: 145–147 °C. 1H-NMR (DMSO,
123