J IRAN CHEM SOC
2,3–Dihydro-2-(4-fluorophenyl)quinazolin-4(1H)-one
(Table 3, entry 9)
(100 MHz, DMSO-d6): d (ppm) = 55.40, 55.51, 66.52,
110.52, 111.16, 117.12, 119.19, 127.31, 133.22, 133.49,
148.05, 148.53, 148.94, 163.74.
Yield: 92 %, white solid, mp 207–209 °C; FT-IR: tmax
(neat) = 3,300 (NH), 3,182 (NH) and 1,653 (C = O)
cm-1; 1H NMR (400 MHz, DMSO-d6): d (ppm) = 5.79 (s,
1H, H2 quinazolinone), 6.69 (t, J = 7.6 Hz, 1H, H6 qui-
nazolinone), 6.76 (d, J = 8.0 Hz, 1H, H8 quinazolinone),
7.13 (s, 1H, NH), 7.22–7.28 (m, 3H, ArH, H7 quinazoli-
none), 7.53–7.57 (m, 2H, ArH), 7.62 (d, J = 7.6 Hz, 1H,
H8 quinazolinone), 8.33 (s, 1H, NH); 13C NMR (100 MHz,
DMSO-d6): d (ppm) = 65.88, 114.40, 114,90, 114,96,
115.18, 117.22, 127.33, 128.98, 129.06, 133.34, 137.71,
137.74, 147.78, 160.86, 163.28, 163.54.
2,3–Dihydro-2-(2-chlorophenyl)quinazolin-4(1H)-one
(Table 3, entry 5)
Yield: 91 %, white solid, mp 215–216 °C; FT-IR: tmax
(neat) = 3,362 (NH), 3,194 (NH) and 1,645 (C = O)
1
cm-1; H NMR (400 MHz, DMSO-d6): d (ppm) = 6.15
(s, 1H, H2 quinazolinone), 6.72 (t, J = 7.6 Hz, 1H, H6
quinazolinone), 6.77 (d, J = 8.0 Hz, 1H, H8 quinazoli-
none), 7.04 (s, 1H, NH), 7.27 (t, J = 7.6 Hz, 1H, H7
quinazolinone), 7.39–7.43 (m, 2H, ArH), 7.49–7.52 (m,
1H, ArH), 7.65–7.69 (m, 2H, H5 quinazolinone,
ArH), 8.22 (s, 1H, NH); 13C NMR (100 MHz, DMSO-
d6): d (ppm) = 63.64, 114.53, 114.63, 127.34, 127.44,
128.72, 129.55, 130.28, 131.81, 133.42, 137.81, 147.62,
163.61.
2,3–Dihydro-2-(4-hydroxyphenyl)quinazolin-4(1H)-one
(Table 3, entry 10)
Yield: 85 %, white solid, mp 213–216 °C; FT-IR: tmax
(neat) = 3,338 (NH), 3,189 (NH) and 1,632 (C = O)
cm-1; 1H NMR (500 MHz, DMSO-d6): d (ppm) = 5.66 (s,
1H H2 quinazolinone), 6.67 (t, J = 7.4 Hz, 1H, H6 qui-
nazolinone), 6.74 (d, 1H, J = 8.1 Hz, 1H, H8 quinazoli-
none), 6.77 (d, J = 8.4 Hz, 2H, ArH), 6.93 (brs, 1H, NH),
7.24 (t, J = 7.2 Hz, 1H, H7 quinazolinone), 7.31 (d,
J = 8.3 Hz, 2H, ArH), 7.61 (d, J = 7.5 Hz, 1H, H5 qui-
nazolinone), 8.08 (brs, 1H, NH), 9.49 (s, 1H, OH); 13C
NMR (125 MHz, DMSO-d6) : d (ppm) = 67.52, 115.24,
115.80, 115.82, 117.89, 128.21, 129.14, 132.48, 134.05,
149.01, 158.55, 164.61.
2,3–Dihydro-2-(3-bromophenyl)quinazolin-4(1H)-one
(Table 3, entry 7)
Yield: 90 %, white solid, mp 225–228 °C; FT-IR: tmax
(neat) = 3,289 (NH), 3,198 (NH) and 1,647 (C = O)
cm-1; 1H NMR (400 MHz, DMSO-d6): d (ppm) = 5.78 (s,
1H, H2 quinazolinone), 6.69 (t, J = 7.6 Hz, 1H, H6 qui-
nazolinone), 6.76 (d, J = 8.0 Hz, 1H, H8 quinazolinone),
7.23 (s, 1H, NH), 7.26 (t, J = 7.2 Hz, 1H, H7 quinazoli-
none), 7.36 (t, J = 8.0 Hz, 1H, ArH), 7.49 (d, J = 8.0 Hz
1H, ArH), 7.54 (d, J = 8.0 Hz, 2H, ArH), 7.61 (d,
J = 7.6 Hz, 1H, H5 quinazolinone), 7.68 (s, 1H, ArH),
8.42 (s, 1H, NH); 13C NMR (100 MHz, DMSO-d6): d
(ppm) = 65.45, 114.43, 114.83, 117.29, 121.55, 125.76,
127.33, 129.62, 130.57, 131.14, 133.45, 144.57, 147.46,
163.38.
2,3–Dihydro-2-(3,4-dihydroxyphenyl)quinazolin-4(1H)-
one (Table 3, entry 15)
Yield: 85 %, white solid, mp 212–214 °C; FT-IR: tmax
(neat) = 3,350 (NH), 3,315 (NH) and 1,636 (C = O)
cm-1; 1H NMR (400 MHz, DMSO-d6): d (ppm) = 5.57 (s,
1H H2 quinazolinone), 6.66 (t, J = 8.0 Hz, 1H, H6 qui-
nazolinone), 6.70–6.75 (m, 3H, H8 quinazolinone, ArH),
6.92 (s, 1H, ArH), 6.93 (brs, 1H, NH), 7.23 (t, J = 8.0 Hz,
1H, H7 quinazolinone), 7.60 (d, J = 8.0 Hz, 1H, H5 qui-
nazolinone), 8.08 (brs, 1 H, NH); 13C NMR (125 MHz,
DMSO-d6): d (ppm) = 66.68, 114.21, 114.27, 114.82,
114.97, 116.86, 118.00, 127.28, 132.24, 133.13, 145.10,
145.63, 148.05, 163.61; Anal. Calcd for C14H12N2O3: C,
65.62; H, 4.72; N 10.93. Found: C, 65.39; H, 4.84; N 10.59.
2,3–Dihydro-2-(4-bromophenyl)quinazolin-4(1H)-one
(Table 3, entry 8)
Yield: 94 %, white solid, mp 200–202 °C; FT-IR: tmax
(neat) = 3,309 (NH), 3,189 (NH) and 1,655 (C = O)
cm-1; 1H NMR (400 MHz, DMSO-d6): d (ppm) = 5.76 (s,
1H, H2 quinazolinone), 6.69 (t, J = 7.6 Hz, 1H, H6 qui-
nazolinone), 6.75 (d, J = 8.0 Hz, 1H, H8 quinazolinone),
7.17 (s, 1H, NH), 7.26 (t, J = 7.6 Hz, 1H, H7 quinazoli-
none), 7.45 (d, J = 8.4 Hz, 2H, ArH), 7.59–7.62 (m, 3H,
ArH, H5 quinazolinone), 8.37 (s, 1H, NH); 13C NMR
(100 MHz, DMSO-d6): d (ppm) = 65.74, 114.42, 114.89,
117.25, 121.54, 127.33, 128.64, 129.06, 129.79, 131.20,
131.61, 133.38, 141.04, 147.60, 163.45.
2,3-Dihydro-2-spirocyclopentylquinazolin-4(1H)-one
(Table 3, entry 17)
Yield: 81 %, white solid, mp 256–258 °C; FT-IR: tmax
(neat) = 3,286 (NH), 3,161 (NH) and 1,643 (C = O)
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