318
Papers
SYNTHESIS
To obtain more information regarding the role of the solvent as toluene, in the presence of a catalytic amount of AlCl3
we tested a variety of experimental conditions on 2-amino-2- gave the triazole derivative 6a instead. The same compound
(benzoylhydrazono)ethyl phenyl ether 3a. We found that 6a was also formed by cyclization of 3a with POCl3.
only the phthalazinone 4a was obtained by mild heating of a
mixture of compound 3a in AcOH/H2SO4 in a 5:1 ratio, It is important to note that, on the basis of compelling
whereas, carryingoutthereactioninanapolarsolvent, such spectroscopic evidence, the heterocyclization does not, in
Table 1. 2-Amino-2-(aroylhydrazono)ethyl Aryl Ethers 3 Prepared
Prod-
ucta
R
H
R¢
Yield mp (°C)b IR (Nujol)
(%)
1H-NMR (DMSO-d6/TMS)
d
(solvent) n (cm–1)
3a
H
50
190
3450, 3380, 4.51 (s, 2H, CH2), 6.54 (s, 2H, NH2), 7.01, 7.29, 7.45, 7.80 (m, 10Harom),
(EtOH)
3160, 1650, 9.87 (s, 1H, NH)
1630
3b
3c
3d
2-CH3
3-CH3
4-CH3
H
H
H
65
80
77
170
(EtOH)
3480, 3200, 2.19 (s, 3H, CH3), 4.52 (s, 2H, CH2), 6.51 (s, 2H, NH2), 6.83, 7.00, 7.43,
1670, 1630
7.80 (m, 9Harom), 9.90 (s, 1H, NH)
168
(EtOH)
3450, 3190
2.25 (s, 3H, CH3), 4.48 (s, 2H, CH2), 6.52 (s, 2H, NH2), 6.80, 7.15, 7.44,
1660, 1600, 7.79 (m, 9Haromm), 9.86 (s, 1H, NH)
170
3470, 3140
2.20 (s, 3H, CH3), 4.48 (s, 2H, CH2), 6.59 (s, 2H, NH2), 6.91, 7.07, 7.43,
(EtOH)
1670, 1625, 7.81 (m, 9Harom), 9.90 (s, 1H, NH)
1605, 1575
3e
3f
2-OCH3
3-OCH3
4-OCH3
2-Cl
3-Cl
4-Cl
4-NO2
H
H
55
87
65
73
85
80
92
78
70
76
78
84
58
190
3400, 3210, 3.75 (s, 3H, CH3), 4.50 (s, 2H, CH2), 6.54 (s, 2H, NH2), 6.87, 6.95, 7.08,
(MeOH) 1670, 1630, 7.43, 7.81 (m, 9Harom), 9.90 (s, 1H, NH)
1610, 1590
H
180
(EtOH)
3420, 3220, 3.68 (s, 3H, CH3), 4.49 (s, 2H, CH2), 6.57 (s, 2H, NH2), 6.51, 7.14, 7.41,
1675, 1645, 7.78 (m, 9Harom), 9.92 (s, 1H, NH)
1600
3g
3h
3i
H
190
(EtOH)
3460, 3150, 3.66 (s, 3H, CH3), 4.45 (s, 2H, CH2), 6.52 (s, 2H, NH2), 6.92, 7.43, 7.79
1675, 1640, (m, 9Harom), 9.86 (s, 1H, NH)
1610, 1580
H
187
(EtOH)
3420, 3190, 4.58 (s, 2H, CH2), 6.54 (s, 2H, NH2), 6.94, 7.24, 7.41, 7.78 (m, 9Harom),
1675, 1640, 9.93 (s, 1H, NH)
1620, 1600
H
190
(EtOH)
3430, 3200, 4.52 (s, 2H, CH2), 6.55 (s, 2H, NH2), 6.98, 7.07, 7.29, 7.43, 7.77 (m,
1680, 1650, 9Harom), 9.87 (s, 1H, NH)
1630, 1600
3j
H
197
(EtOH)
3440, 3190, 4.53 (s, 2H, CH2), 6.60 (s, 2H, NH2), 7.04, 7.32, 7.44, 7.80 (m, 9Harom),
1680, 1640, 9.89 (s, 1H, NH)
1625, 1595
3k
3l
H
148
(PrOH)
3440, 3350, 4.70 (s, 2H, CH2), 6.55 (s, 2H, NH2), 7.21, 7.34, 7.87, 8.18 (m, 9Harom +
3170, 1620, NH)
1585
2-CH3
3-CH3
4-CH3
2-Cl
3-Cl
4-Cl
185
(PrOH)
3440, 3230, 2.28 (s, 3H, CH3), 4.46 (s, 2H, CH2), 6.40 (s, 2H, NH2), 6.82–7.32 (m,
1690, 1650, 9Harom), 9.81 (s, 1H, NH)
1630, 1600
3m
3n
3o
3p
3q
H
150
(EtOH)
3460, 3210, 2.31 (s, 3H, CH3), 4.49 (s, 2H, CH2), 6.53 (s, 2H, NH2), 6.94, 7.00, 7.27,
1690, 1655, 7.60 (m, 9Harom), 9.83 (s, 1H, NH)
1630
H
190
(PrOH)
3460, 3430, 2.30 (s, 3H, CH3), 4.49 (s, 2H, CH2), 6.54 (s, 2H, NH2), 6.92, 6.99, 7.27,
3220, 1675, 7.70 (m, 9Harom), 9.82 (s, 1H, NH)
1630
H
195
(PrOH)
3420, 3210, 4.47 (s, 2H, CH2), 6.41 (s, 2H, NH2), 6.83–7.48 (m, 9Harom), 9.96 (s, 1H,
1680, 1640, NH)
1615, 1590
H
150
(EtOH)
3430, 3220, 4.51 (s, 2H, CH2), 6.62 (s, 2H, NH2), 6.93, 6.99, 7.26, 7.43, 7.80 (m,
1680, 1640, 9Harom), 10.00 (s, 1H, NH)
1620, 1600
H
180
3440, 3370, 4.50 (s, 2H, CH2), 6.58 (s, 2H, NH2), 6.98, 7.27, 7.47, 7.83 (m, 9Harom),
(PrOH)
3230, 1680
1645, 1620
9.94 (s, 1H, NH)
a Satisfactory microanalyses obtained for all compounds.
b Uncorrected melting points.