J Fluoresc (2014) 24:1571–1580
1579
potassium carbonate was removed by filtration and the N,N-
dimethylformamide was removed under the vacuum
rotavapour and washed with water and hexane to obtain
solid product. The compound is characterized by NMR
and mass spectral data. Yield (88.2 %), m.p. 230-234 °C.
1H NMR (300 MHz, CDCl3): δ=8.61 (d, 2H, naphthalene,
J=7.2 Hz), 8.21 (d, 2H, naphthalene, J=8.1 Hz), 7.76 (t, 2H,
naphthalene, J=7.55 Hz), 7.43 (d, 1H, J=8.68 Hz, ArH),
6.83 (dd, 1H, J1=2.45, J2=8.68, ArH), 6.77 (d, 1H, J=2.45,
ArH), 6.11 (s, 1H), 4.28 (t, 2H, J=6.79), 4.08 (t, 2H, J=
5.85), 2.37 (s, 3H), 1.92–2.01 (m, 4H, 2-CH2). 13C NMR
(100 MHz, DMSO-d6): δ 163.96, 162.17, 160.41, 155.23,
153.45, 134.57, 131.81, 131.07, 127.92, 127.51, 126.63,
113.61, 112.81, 111.63, 101.95, 68.58, 26.64, 24.70, 18.36.
MS(ESI): M+1 m/z 428.
126.75, 125.20, 123.06, 113.49, 112.56, 111.96, 101.80,
68.71, 40.30, 28.95(3 C), 27.96, 26.85, 25.76, 18.16.
MS(ESI) : M+1 m/z 484
2-[4-(1,4-Dioxo-1,2,3,4-tetrahydrophthalazin-5-
ylamino)butyl]-1H-benzo[de]isoquinoline-1,3(2H)-
dione (5a): Yield (76.8 %), 1H NMR (400 MHz, CDCl3+
DMSO-d6): δ=8.53 (d, 2H, naphthalene, J=7.3 Hz), 8.27
(d, 2H, naphthalene, J=8.1 Hz), 7.84 (t, 2H, naphthalene,
J=7.6 Hz), 7.35 (t, 1H, aromatic, J=7.9 Hz), 6.97 (d, 1H,
aromatic, J=6.9 Hz), 6.81 (d, 1H, aromatic, J=8.3 Hz),
4.24 - 4.14 (m, 4H), 1.97 -1.85 (m, 4H), 11.02 (s, 1H,
NH, D2O exchange), 5.95 (s, 2H, NH, D2O exchange).
MS(ESI) : M+1 m/z 429
2-[5-(1,4-Dioxo-1,2,3,4-tetrahydrophthalazin-5-
ylamino)pentyl]-1H-benzo[de]isoquinoline-1,3(2H)-
dione (5b): Yield (75.2 %), 1H NMR (400 MHz, CDCl3
+DMSO-d6): δ=8.58 (d, 2H, naphthalene, J=7.17 Hz),
8.27 (d, 2H, naphthalene, J=8.1 Hz), 7.78 (t, 2H, naph-
thalene, J=7.5 Hz), 7.37 (t, 1H, aromatic, J=7.7 Hz), 7.05
(d, 1H, aromatic, J=7.6 Hz), 6.84 (d, 1H, aromatic, J=
8.3 Hz), 4.26 - 4.19 (m, 4H), 1.97-1.58 (m, 6H), 10.62 (s,
1H, NH, D2O exchange), 6.75 (s, 2H, NH, D2O ex-
change). MS(ESI): M+1 m/z 443
2-[6-(1,4-Dioxo-1,2,3,4-tetrahydrophthalazin-5-
ylamino)hexyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione
(5c): Yield (74.6 %), 1H NMR (300 MHz, CDCl3 +DMSO-
d6): δ=8.59 (d, 2H, naphthalene, J=7.2 Hz), 8.20 (d, 2H,
naphthalene, J=8 Hz), 7.74 (t, 2H, naphthalene, J=7.2 Hz),
7.45 (t, 1H, aromatic, J=8 Hz), 7.14 (d, 1H, aromatic, J=
7.6 Hz), 6.79 (d, 1H, aromatic, J=8 Hz), 4.23 - 4.16 (m,
4H), 1.85 -1.58 (m, 8H), 9.11 (s, 1H, NH, D2O exchange),
6.35 (s, 2H, NH, D2O exchange). MS : M+1 m/z 457
2-[8-(1,4-Dioxo-1,2,3,4-tetrahydrophthalazin-5-
ylamino)octyl]-1H-benzo[de]isoquinoline-1,3(2H)-
dione (5d): Yield (72.7%), 1H NMR (400 MHz, CDCl3):
δ=8.62 (d, 2H, naphthalene, J=6.8 Hz), 8.22 (d, 2H,
naphthalene, J=8.4 Hz), 7.77 (t, 2H, naphthalene, J=
7.6 Hz), 7.491 (t, 2H, aromatic, J=8 Hz), 7.17 (d, 2H,
aromatic, J=7.6 Hz), 6.82 (d, 2H, aromatic, J=8 Hz),
4.24 - 4.18 (m, 4H), 1.84 -1.75 (m, 4H), 1.35-1.58 (m,
8H), 8.99 (s, 1H, NH, D2O exchange), 6.37 (s, 2H, NH,
D2O exchange). MS : M+1 m/z 485.
Employing above procedure compounds 4b, 4c, 4d, 5a,
5b, 5c and 5d were synthesized and characterized as follows.
2-[5-(4-Methyl-2-oxo-2H-chromen-7-yloxy)pentyl]-1H-
benzo[de]isoquinoline-1,3(2H)-dione (4b): Yield
1
(86.7 %), H NMR (400 MHz, CDCl3): δ=8.63 (d, 2H,
naphthalene, J=7.2 Hz), 8.24 (d, 2H, naphthalene, J=
8.4 Hz), 7.78 (t, 2H, naphthalene, J=7.6 Hz),7.48 (d, 1H,
J=8.8 Hz, ArH), 6.85 (dd, 1H, J1=2.46, J2=8.69, ArH),
6.80 (d, 1H, J=2.34, ArH), 6.14 (d, 1H, J=0.8 Hz), 4.25 (t,
2H, J=7.6), 4.05 (t, 2H, J=6.4), 2.37 (d, 3H, J=1.2 Hz),
1.62–1.95 (m, 6H, 2-CH2). MS(ESI) : M+1 m/z 442
2-[6-(4-Methyl-2-oxo-2H-chromen-7-yloxy)hexyl]-
1H-benzo[de]isoquinoline-1,3(2H)-dione (4c): Yield
(84.8 %), 1H NMR (400 MHz, CDCl3): δ=8.59 (d, 2H,
naphthalene, J=7.36 Hz), 8.20 (d, 2H, naphthalene, J=
8.12 Hz), 7.75 (t, 2H, naphthalene, J=7.8 Hz),7.45 (d,
1H, J=8.8 Hz, ArH), 6.81 (dd, 1H, J1=2.46, J2=8.69,
ArH), 6.77 (d, 1H, J=2.46, ArH), 6.10 (d, 1H, J=0.8 Hz),
4.19 (t, 2H, J=7.3), 4.01 (t, 2H, J=6.42), 2.39 (d, 3H, J=
13
1.1 Hz), 1.51–1.89 (m, 8H, 4-CH2).
C NMR
(100 MHz, CDCl3): δ 164.01, 162.33, 160.76, 155.51,
151.88, 133.50, 131.71, 130.94, 128.27, 126.76, 125.20,
123.01, 113.50, 112.52, 111.97, 111.89, 101.82, 101.76,
68.64, 40.14, 28.82, 27.92, 26.64, 25.59, 18.16. MS(ESI)
: M+1 m/z 456
2-[8-(4-Methyl-2-oxo-2H-chromen-7-yloxy)octyl]-1H-
benzo[de]isoquinoline-1,3(2H)-dione (4d): Yield
(82.8 %), 1H NMR (400 MHz, CDCl3): δ=8.59 (d, 2H,
naphthalene, J=7.17 Hz), 8.20 (d, 2H, naphthalene, J=
7.74 Hz), 7.75 (t, 2H, naphthalene, J=7.93 Hz),7.46 (d,
1H, J=8.87 Hz, ArH), 6.84 (dd, 1H, J1=2.44, J2=8.68,
ArH), 6.79 (d, 1H, J=2.45, ArH), 6.11 (s, 1H), 4.17 (t,
2H, J=7.5), 3.99 (t, 2H, J=6.42), 2.38 (s, 3H), 1.826-1.64
(m, 6H, 3-CH2),1.15-1.30 (m, 6H, 3-CH2). 13C NMR
(100 MHz, DMSO-d6): δ 163.99, 162.38, 160.77,
155.52, 151.89, 133.45, 131.70, 130.91, 128.28,
Acknowledgments We wish to gratefully acknowledge the financial
support from Department of Biotechnology, Ministry of Science and
Technology, Government of India.
References
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