964
BEREZINA at al.
soluble in benzene, ethanol, DMF, chloroform, and
acetone; insoluble in hexane, heptane, and 20% alkali.
UV spectrum, max, nm (ethanol): 376, 585; (benzene):
382, 558; (DMF): 536; (chloroform): 378, 562;
(CH) 826. Found N, %: 3.6. C44H28N2O4S. Cal-
culated N, %: 4.1.
1-(4-[(4-[3-(Benzoyloxy)-1H-inden-1-yliden]-
aminophenoxy]phenylimino)-1H-inden-3-yl
benzoate (X), yield 22%, brown crystals, does not
melt up to 300 C, Rf 0.92. UV spectrum, max, nm
1
(acetone): 381, 569. IR spectrum, cm : (NH) 3382,
(NH) 1505, (C=O) 1658, (CN) 1208, (CC) 1106,
(CS) 728, (CH) 2921, (CH) 833, (S=O) 1145.
Found N, %: 5.3. C30H20N2O4S. Calculated N, %:
5.6.
1
(DMF): 300 (log 4.5). IR spectrum, cm : (C=O)
1716, (CC) 1093, .(C=N) 1616, (CH) 2920, (CH)
842, (CO) 1236. Found N, %: 4.4. C44H28N2O5.
Calculated N, %: 4.2.
Compounds VI, VII, and XIV XVIII were pre-
pared in a similar way.
1,7(1,3)-Di-1H-indena-3,5,9,11(1,4)-tetrabenzola-
2,6,8,12-tetraaza-4,10-dithiacyclododecaphane-1,6-
diene-4,10-dione (XI). A mixture of 0.0003 mol of
compound V and 0.002 mol of sulfone II was heated
in 15 ml of glacial acetic acid under reflux for 3 h.
After cooling, the reaction mixture was poured into
hexane. A precipitate formed and was filtered off and
dried at 100 C, yield 87%, light brown crystals, mp
225 C, Rf 0.6, soluble in DMF, acetone, ethanol and
chloroform (under heating), and insoluble in hexane
and HCl. UV spectrum, max, nm· (ethanol): 305. IR
3-[4-(4-[(1-Oxo-1H-inden-3-yl)amino]phenylsul-
fanyl)anilino]-1H-inden-1-one (VI), yield 75%, dark
green crystals, mp 176 C, Rf 0.6. UV spectrum,
,
max
nm (ethanol): 385, 596; (benzene): 376, 575; (DMF):
385,585; (acetone): 377, 582; (chloroform): 378, 512,
1
584. IR specrum, cm : (NH) 3373, (NH) 1547,
(C=O) 1649, (CN) 1207, (CC) 1102, (CS) 735,
(CH) 2918, (CH) 817. Found N, %: 6.1. C30H20
N2O2S. Calculated N, %: 5.9.
3-(4-4-[(1-Oxo-1H-inden-3-yl)amino]phenoxy-
anilino)-1H-inden-1-one (VII), yield 77%, violet
crystals, mp 256 C, Rf 0.77. UV spectrum, max, nm
(DMF): 394 (log 4.5), 585 (log 4.2). IR spectrum,
1
spectrum, cm : (NH) 3373, (NH) 1522, (CN)
1401, (CC) 1073, (C=N) 1675, (CS) 734, (CH)
2920, (CH) 833, (S=O) 1148, 1320. Found N, %:
8.2. C42H28N4O4S2. Calculated N, %: 7.8.
1
cm : (NH) 3437, (NH) 1549, (C=O) 1654, (CN)
1448, (CC) 1093, (CH) 2921, (CH) 833, (CO)
1204. Found N, %: 5.5. C30H20N2O3. Calculated N,
%: 6.1.
1,7(1,3)-Di-1H-indena-3,5,9,11(1,4)-tetrabenzola-
2,6,8,12-tetraaza-4,10-dithiacyclododecaphane-1,6-
diene (XII), yield 29%, dark brown crystals, does not
melt up to 250 C, Rf 0.65, soluble in acetone, ethanol,
and chloroform. UV spectrum, max, nm (DMF): 416
1-(4-[(4-[3-(Benzoyloxy)-1H-inden-1-yliden]-
aminophenyl)sulfonyl]phenylimino)-1H-inden-3-yl
benzoate (VIII). A mixture of 0.02 mol of compound
V, 13 ml of benzoyl chloride, and 5 ml of pyridine
was heated under reflux for 6 h. After cooling, a
precipitate formed and was filtered off, washed with
benzene, dissolved in 5% alkali, filtered off, and dried
at 100 C. Organic admixtures were extracted in a
Soxhlet apparatus with benzene. Yield 52%, brown
crystals, does not melt up to 250 C, Rf 0.9, soluble in
chloroform, acetone, and DMF (under heating), and
insoluble in benzene. UV spectrum, max, nm (chlo-
1
(log 4.7). IR spectrum, cm : (NH) 3415, (NH)
1540, (CN) 1398, (CC) 1049, (C=N) 1606, (CS)
747, (CH) 2923, (CH) 830. Found N, %: 7.9.
C42H28N4S2. Calculated N, %: 8.6.
1,7(1,3)-Di-1H-indena-3,5,9,11(1,4)-tetrabenzola-
2,6,8,12-tetraaza-4,10-dioxacyclododecaphane-1,6-
diene (XIII), yield 38%, dark brown crystals, does not
melt up to 300 C, Rf 0.7, soluble in DMF and in-
soluble in ethanol, acetone, and chloroform. UV spec-
trum, max, nm (DMF): 293 (log 4.6). IR spectrum,
1
1
roform): 299. IR spectrum, cm : (C=O) 1720,
cm : (NH) 3416, (NH) 1538, (CN) 1405, (CC)
(CC) 1072, (C=N) 1664, (CS) 710, (CH) 2918,
(CH) 794, (S=O) 1152. Found N, %: 3.8.
C44H28N2O6S. Calculated N, %: 33.9.
1093, .(C=N) 1614, (CH) 2920, (CH) 834, (CO)
1219. Found N, %: 8.5. C42H28N4O2. Calculated N,
%: 9.03.
Compounds IX and X were prepared in a similar
way.
N,N -Bis(1-oxo-1H-inden-3-yl)-m-phenylenedi-
amine (XIV), yield 88%, red crystals, mp 291 293 C,
Rf 0.7. UV spectrum, max, nm (ethanol): 470 (log
1-(4-[(4-[3-(Benzoyloxy)-1H-inden-1-yliden]-
aminophenyl)sulfanyl]phenylimino)-1H-inden-3-yl
benzoate (IX), yield 44%, brown crystals, does not
melt up to 250 C, Rf 0.85. UV spectrum, .max, nm
1
3.77). IR spectrum, cm : (NH) 3370, (NH) 1540,
(C=O) 1680, (CN) 1240, (CC) 1120, (CH) 2920,
(CH) 796. Found N, %: 8.0. C24H16N2O2. Calculated
N, %: 7.7.
1
(ethanol): 401. IR spectrum, cm : (C=O) 1713,
(CC) 1084, (C=N) 1656, (CS) 752, (CH) 2973,
N,N -Bis(1-oxo-1H-inden-3-yl)pyridine-2,6-di-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 75 No. 6 2005