1148
K. M. El-Shaieb et al. · Condensation Reactions of 2-Aminobenzohydrazide
ν = 3417, 3390, 3201, 1678 cm−1. – 1H NMR (400 MHz, was refluxed for 6 h. A colorless precipitate was formed.
[D6]DMSO): δ = 6.34 (s, 2H, NH2), 6.45 – 6.76 (m, 4H, After completing the reaction (TLC follow), the precipitate
ArH), 7.23 – 7.85 (m, 5H), 8.81 (s, 1 H, NH), 9.88 (s, 1H, was filtered off, washed and recrystallized from DMF/EtOH.
CHO) ppm. – MS (EI, 70 eV): m/z (%) = 269 (15) [M+2]+, Colorless powder (yield: 82%), m. p. 198 – 200 ◦C. – IR
267 (34) [M]+, 251 (16), 244 (14), 232 (46), 223 (42), 211 (film): ν = 3313, 3201, 1643, 1612, cm−1. – 1H NMR
(14), 192 (17), 182 (48), 179 (48), 157 (27), 154 (46), 149 (400 MHz, [D6]DMSO): δ = 1.80 (m, 2H, CH2), 2.20 (m,
(20), (52), 137 (52), 114 (36), 91 (41), 81 (76), 62 (56), 60 2H, CH2), 2.55 (m, 2H, CH2), 3.35 (m, 2H, CH2), 4.75
(43), 48 (100). – C15H13N3O2 (267.28): calcd. C 67.40, H (s, 2H, NCH2Ph), 7.42 (brs, 2H, NH2), 6.70 – 7.65 (m, 9H,
4.90, N 15.72; found C 67.21, H 4.83, N 15.57.
ArH), 9.60 (brs, 1 H, NH) ppm. – 13C NMR (150 MHz,
[D6]DMSO): δ = 22.00 (4CH2), 48.00 (NCH2), 114.00 (C-
2), 115.00, 126.00, 127.00, 128.00, 129.00 (CH-Ar), 134.00,
138.00, 146.00 (C-Ar), 163.00 (C=O) ppm. – MS (EI,
70 eV): m/z (%) = 323 (4) [M+1]+, 322 (9) [M]+, 306 (20),
278 (14), 231 (11), 203 (15), 188 (16), 176 (10), 172 (17),
160 (6), 146 (22), 91 (100), 77 (5). – C19H22N4O (322.40):
calcd. C 70.78, H 6.88, N 17.38; found C 70.49, H 6.78, N
17.21.
Synthesis of N0,N000-(1,4-phenylenebis(methanylidene))-
bis(2-aminobenzohydrazide) (4)
A mixture of compound 2 (134 mg, 1 mmol), compound 1
(302 mg, 2 mmol) and a catalytic amount of iodine in ethanol
(20 mL) was refluxed, and a yellow precipitate was formed
after 30 min. The reaction was continued for 2 h. After com-
pletion of the reaction (monitoring by TLC), the precipitate
was filtered off and washed with DMF. (The product is in-
soluble in the available deuterated solvents). Yellow pow-
der (yield: 75%), m. p. 280 – 282 ◦C. – IR (film): ν = 3435,
3275, 1655, 1614 cm−1. – MS (EI, 70 eV): m/z (%) = 399
(15) [M–1]+, 337 (8), 308 (4), 306 (8), 288 (12), 260 (10),
231 (6), 198 (8), 182 (26), 169 (30), 153 (68), 145 (51),
131 (44), 111 (100), 107 (51), 81 (72), 70 (69), 76 (11).
– C22H20N6O2 (400.43): calcd. C 65.99, H 5.03, N 20.99;
found C 65.80, H 4.95, N 20.79.
Synthesis of 30-amino-10H-spiro[indene-2,20-quinazoline]-
1,3,40(30H)-trione (10)
A mixture of 9 (178 mg, 1 mmol) and 1 (151 mg, 1 mmol)
in the presence of a catalytic amount of iodine in ethanol
(20 mL) was heated under reflux conditions. A brown pre-
cipitate was formed, and the reaction was continued for
a further 2 h. The precipitate was filtered off and recrystal-
lized from 1,4-dioxane. Brown powder (yield: 70%), m. p.
295 – 297 ◦C. – IR (film): ν = 3448, 3336, 3247, 3058, 1678,
1617 cm−1. – 1H NMR (400 MHz, [D6]DMSO): δ = 6.05
(brs, 2H, NH2), 6.70 – 6.80 (m, 2H, ArH), 6.30 – 8.00 (m, 7H,
ArH + NH) ppm. – MS (EI, 70 eV): m/z (%) = 292 (5) [M–
1]+, 263 (6), 262 (2), 248 (9), 239 (9), 235 (4), 22 (10), 219
(8), 146 (3), 136 (7), 121 (9), 120 (100), 119 (10), 92 (25),
91 (4), 65 (13). – C16H11N3O3 (293.28): calcd. C 65.53, H
3.78, N 14.33; found C 65.34, H 3.71, N 14.20.
Synthesis of (E)-2-amino-N0-(4-paracyclophanylidene)-
benzohydrazide (6)
A solution of 1 in dry EtOH (151 mg, 1 mmol) was
mixed with a solution of an equimolar amount of 5 (236 mg,
1 mmol) in dry EtOH (15 mL) in the presence of a catalytic
amount of iodine The mixture was refluxed for 2 h. An or-
ange precipitate was formed. The precipitate was collected,
washed and recrystallized from 1,4-dioxane. Orange pow-
der (yield: 45%), m. p. 232 – 234 ◦C. – IR (film): ν = 3417,
3390, 3201, 1678 cm−1. – 1H NMR (400 MHz, [D6]DMSO):
δ = 2.64 – 2.65 (m, 2H, CH2), 2.94 – 3.18 (m, 6H, 3CH2),
6.35 (s, 2H, NH2), 6.47 – 6.74 (m, 4H, ArH), 7.07 – 7.09 (d,
1H, ArH, J = 2.0 Hz), 7.20 – 7.29 (t, 1H, ArH, J = 4.0 Hz),
7.45 – 7.47 (m, 1H, ArH), 7.59 – 7.66 (m, 4H, ArH), 8.22 (s,
1 H, CH), 8.59 (s, 1 H, NH) ppm. – MS (EI, 70 eV): m/z
(%) = 369 (30) [M]+, 290 (10), 274 (12), 260 (12), 249 (2),
248 (10), 222 (14), 160 (2), 143 (12), 127 (14), 115 (10), 104
(18), 103 (26), 91 (77), 77 (100). – C24H23N3O (369.46):
calcd. C 78.02, H 6.27, N 11.37; found C 77.78, H 6.21, N
11.17.
Synthesis of 30-amino-10H-spiro[cyclohexane-1,20-quin-
azoline]-2,40(30H)-dione (12)
The reactants 1 (151 mg, 1 mmol) and 11 (112 mg,
1 mmol) were dissolved in ethanol (20 mL), and a catalytic
amount of iodine was added. The reaction mixture was boiled
for 2 h and then poured onto cold water (25 mL). A yel-
low precipitate was formed, separated by filtration and re-
crystallized from chloroform/petroleum ether. Yellow pow-
der (yield: 65%), m. p. 180 – 182 ◦C. – IR (film): ν =
3410, 3335, 3210, 1670, 1545 cm−1. – 1H NMR (400 MHz,
[D6]DMSO): δ = 1.23 – 2.15 (m, 8H , 4CH2), 6.63 (brs, 2H,
NH2), 6.78 – 7.08 (m, 4H, ArH), 7.64 (s, 1H, NH) ppm. – MS
(EI, 70 eV): m/z (%) = 246 (14) [M+1]+, 245 (100) [M]+,
228 (16), 217 (60), 200 (83), 172 (93), 156 (42), 149 (17),
Synthesis of 30-amino-1-benzyl-10H-spiro[piperidine-4,20-
quinazolin]-40(30H)-one (8)
A mixture of 1 (151 mg, 1 mmol), compound 7 (189 mg, 128 (41), 104 (38), 77 (15). – C13H15N3O2 (245.28): calcd.
1 mmol) and a catalytic amount of iodine in ethanol (20 mL) C 63.66, H 6.16, N 17.13; found C 63.44, H 6.13, N 16.99.
Brought to you by | University of California
Authenticated
Download Date | 6/8/15 2:16 PM