Month 2017
Synthesis of Heterocyclic Compounds via Benzoxazinone
C22H15IN2O3: C, 54.79; H, 3.14; N, 5.81. Found: C, 54.21;
4.3 Hz, 1H, Ar3H), 8.32 (d, J = 2.2 Hz, 1H, Ar1-H), 8.25
(bs, 1H, NH, exchangeable by D2O), 8.15 (dd, J = 11.0,
4.3 Hz, 1H, Ar3H), 7.71 (dd, J = 8.2, 2.5 Hz, 1H, Ar1-
H), 7.67 (d, J = 6.8 Hz, 2H, Ar2-H), 7.51 (d, J = 8.3 Hz,
H, 2.88; N, 5.10. EIMS (M+.) m/z: 482.
2-(3-(4-Hydroxybutyl)-6-iodo-4-oxo-3,4-dihydro quinazolin-2-yl)
benzoic acid (6). Colorless crystals, yield 65% yield as m.
p. 106─108°C; 1H NMR (CDCl3, 400 MHz) 12.94 (bs, 1H,
COOH exchangeable by D2O), 8.12 (d, J = 2.2 Hz, 1H,
Ar1-H), 8 .11 (d, J = 9.9 Hz, 2H, Ar2-H), 7.80 (dd,
J = 8.2, 2.5 Hz, 1H, Ar1-H), 7.58 (dd, J = 7.9, 3.2 Hz,
2H, Ar2-H), 7.23 (dd, J = 8.2 Hz, 1H, Ar1-H), 5.50 (s,
1H, OH exchangeable by D2O), 3.82 (t, J = 7.3 Hz, 2H,
OCH2), 2.64 (t, J = 7.6 Hz, 2H, NCH2), 1.71–1.64 (m,
4H, CH2CH2). FTIR (KBr, cmꢀ1) vmax: 3225 (broad),
3017, 2920, 1671, 1621 cmꢀ1; Calculated Anal. Calcd
for C19H17IN2O4: C, 49.16; H, 3.69; I, 27.33; N, 6.03;
found C, 49.21; H, 3.55; I, 27.12; N, 6.24. EIMS (M+.)
2H, Ar2H), 7.51 (dd, J = 10.9, 4.2 Hz, 2H, Ar3-H), 7.39
1
(dd, J = 8.2 Hz, 1H, Ar1-H). FTIR (KBr, cm ) vmax
:
3212 (N─H), 2953, 2872, 1753 (C═O), 1310 (vas (C–O–
C)), 1262 (va (C–O–C)). Anal. Calcd for C20H12IN3O3: C,
51.19; H, 2.58; N, 8.96. Found: C, 50.88; H, 2.25; N,
8.46. EIMS (M+.) m/z: 469.
30-(Pyridin-2-ylmethyl)-10H,3H-spiro[isobenzofuran-1,20-
quinazoline]-3,40(30H)-dione (11).
White crystal, yield
1
70%; H NMR (CDCl3, 400 MHz) 8.29 (bs, 1H, NH,
exchangeable by D2O), 8.24 (d, J = 7.2 Hz, 2H, Ar1-
H), 7.71 (dd, J = 8.2, 2.5 Hz, 1H, Ar1-H), 7.67 (d,
J = 6.8 Hz, 2H, Ar2-H), 7.51 (d, J = 8.3 Hz, 2H,
Ar2H), 8.15 (dd, J = 11.0, 4.3 Hz, 2H, Ar3H), 7.51 (dd,
J = 10.9, 4.2 Hz, 2H, Ar3-H), 7.39 (dd, J = 8.2 Hz,
m/z: 464.
2-(6-Iodo-4-oxo-3-(2,4,5-trihydroxy-6-(hydroxymethyl)-2-
methyltetrahydro-2H-pyran-3-yl)-3,4-dihydro quinazolin-2-yl)
1
benzoic acid (7). Yellow crystal, yield 78.8%; H NMR
1H, Ar1-H), 4.51 (s, 1H, Py-CH2). FTIR (KBr, cmꢀ1
)
(CDCl3, 400 MHz) 12.92 (bs, 1H, COOH, exchangeable
by D2O), 8.28 (d, J = 2.2 Hz, 1H, Ar1-H), 7.91 (dd,
J = 7.9, 3.2 Hz, 2H, Ar2-H), 7.73 (dd, J = 8.2, 2.5 Hz,
1H, Ar1-H), 7.51 (dd, J = 7.9, 3.2 Hz, 2H, Ar2-H), 7.39
(dd, J = 8.2 Hz, 1H, Ar1-H), 4.37–4.12 (m, 4H, gluOH,
exchangeable by D2O), 3.81–3.62 (m, 5H, gluCH), 3.55
(s, 2H, gluCH2), 3.32–1.33 (d, 1H, gluCH). FTIR (KBr,
cmꢀ1) vmax: 3210 (N─H), 2952, 2870, 1751, 1542
(C═O), 1312 (vas (C–O–C)), 1252 (va (C–O–C)). Anal. Calcd
for C22H21IN2O8: C, 46.50; H, 3.72; N, 4.93. Found: C,
46.25; H, 3.49; N, 4.48. EIMS (M+.) m/z: 568.
v
max: 3210 (N─H), 3052 (ArCH), 2952, 2870 (AliCH),
1750, 1680 (C═O), 1312 (vas (C–O–C)), 1260 (va (C–O)).
Anal. Calcd for C21H15N3O3: C, 70.78; H, 4.21; N,
11.79. Found: C, 70.50; H, 4.05; N, 11.27. EIMS (M+.)
m/z: 356.
2-(60-Iodo-3,40-dioxo-10,40-dihydro-3H,30H-spiro[isobenzofuran-
1,20-quinazolin]-30-yl)acetic acid (12).
White crystal, yield
1
76.4%; H NMR (CDCl3, 400 MHz) 13.2 (bs, 1H, COOH
exchangeable by D2O), 8.34 (d, J = 2.2 Hz, 1H, Ar1-H),
8.16 (dd, J = 7.9, 3.2 Hz, 2H, Ar2-H), 7.71 (dd, J = 8.2,
2.5 Hz, 1H, Ar1-H), 7.51 (dd, J = 7.9, 3.2 Hz, 2H, Ar2-H),
7.39 (dd, J = 8.2 Hz, 1H, Ar1-H), 4.52 (s, 1H, Py-CH2).
FTIR (KBr, cmꢀ1) vmax: 3412 (OH), 3218 (N─H), 2952,
2873 (AliCH), 1749, 1705 (C═O), 1542 (NO2), 1305 (vas(C–
O–C)), 1250 (va(C–O–C)). FTIR (KBr, cmꢀ1) vmax: 3356 (OH),
3213 (NH), 2950, 2874, 1750 (C═O), 1310 (vas (C–O–C)),
1256 (va (C–O–C)). Anal. Calcd for C17H11IN2O5: C, 45.36;
H, 2.46, N, 6.22. Found: C, 45.05; H, 2.21; N, 5.94. EIMS
(M+.) m/z: 450.
2-(3-Hydroxy-6-iodo-4-oxo-3,4-dihydroquinazolin-2-yl)
1
benzoic acid (8). Yellow crystal, yield 75.3%; H NMR
(CDCl3, 400 MHz) 13.32 (bs, 1H, COOH, exchangeable
by D2O), 10.52 (bs, 1H, OH, exchangeable by D2O), 8.28
(d, J = 2.5 Hz, 1H, Ar1-H), 8.03 (dd, J = 7.9, 3.2 Hz, 2H,
Ar2-H), 7.93 (dd, J = 8.2, 2.5 Hz, 1H, Ar1-H), 7.51 (dd,
J = 7.9, 3.2 Hz, 2H, Ar2-H), 7.39 (dd, J = 8.2 Hz, 1H,
Ar1-H), FTIR (KBr, cmꢀ1) vmax: 3410 (O─H), 3213
(N─H), 2950, 2874 (AliCH), 1690 (C═O), 1256 (v (C–O)).
Anal. Calcd for C15H9IN2O4: C, 44.14; H, 2.22; N, 6.68.
Found: C, 43.90; H, 1.95; N, 6.25. EIMS (M+.) m/z: 408.
10-Iodo-6H-phthalazino[1,2-b]quinazoline-5,8-dione
2-(3-(40-Amino-2,20-dimethyl-[1,10-biphenyl]-4-yl)-6-iodo-4-
oxo-3,4-dihydroquinazolin-2-yl)benzoic acid (13).
White
1
crystal, yield 56.3%; H NMR (DMSO, 400 MHz) 8.34
(d, J = 2.2 Hz, 1H, Ar1-H), 9.2 (bs, 2H, NH2
exchangeable by D2O), 8.22 (bs, 1H, COOH,
exchangeable by D2O), 8.16 (dd, J = 7.9, 3.2 Hz, 2H,
Ar2-H), 7.71 (dd, J = 8.2, 2.5 Hz, 1H, Ar1-H), 7.51 (dd,
J = 7.9, 3.2 Hz, 2H, Ar2-H), 7.39 (dd, J = 8.2 Hz, 1H,
Ar1-H), 8.16 (dd, J = 7.9, 3.2 Hz, 2H, Ar4-H), 7.21 (dd,
J = 8.2, 2.5 Hz, 1H, Ar4-H), 7.11 (dd, J = 7.9, 3.2 Hz,
1H, Ar3-H), 6.69 (dd, J = 8.2 Hz, 2H, Ar3-H), 2.21 (s,
6H, 2CH3). FTIR (KBr, cmꢀ1) vmax: 3412, 3218 (N─H),
2952, 2873 (AliCH), 1767 (C═O) 1305 (vas(C–O–C)), 1250
(va(C–O–C)). Anal. Calcd for C29H22IN3O3 C, 59.30; H,
3.78; N, 7.15; found C, 59.16; H, 3.86; N, 7.33. EIMS
(M+.) m/z: 587.
(9).
Yellow crystal, yield 22.8%; 1H NMR (CDCl3,
400 MHz) 12.19 (bs, 1H, N─H, exchangeable by
D2O), 8.32 (d, J = 3.1 Hz, 1H, Ar1-H), 8.05 (dd,
J = 7.6, 3.2 Hz, 2H, Ar2-H), 7.86 (dd, J = 8.0, 3.1 Hz,
1H, Ar1-H), 7.63 (dd, J = 7.6, 3.2 Hz, 2H, Ar2-H),
7.39 (d, J = 8.0 Hz, 1H, Ar1-H). FTIR (KBr, cmꢀ1
)
v
max: 3215 (N─H), 2950, 2871 (AliCH), 1659 (C═O),
1305 (vas (C–O)). Anal. Calcd for C15H8IN3O3: C,
46.30; H, 2.07; N, 10.80. Found: C, 46.00; H, 1.89; N,
10.23. EIMS (M+.) m/z: 389.
60-Iodo-30-(pyridin-2-yl)-10H,3H–spiro[isobenzofuran-1,20-
quinazoline]-3,40(30H)-dione (10).
75.3%; H NMR (CDCl3, 400 MHz) 8.38 (dd, J = 11.0,
White crystal, yield
1
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet