Concise Report
Wangꢀetꢀal.
thiazole‐5‐H), 5.38 (s, 2H, CH
2
), 3.78—3.73 (m, 1H, CH),
), 1.07 (d, J = 2.9 Hz, 2H,
); C NMR (151 MHz, CDCl
0.33 mmol) and diphenyl hydrazinylphosphonate (165 mg, 0.66
mmol) in ethanol was added sodium acetate (53 mg, 0.66 mmol).
1
.15—1.10 (m, 2H, cyclopropylimino‐CH
2
13
cyclopropylimino‐CH
1
1
2
3
) δ: 169.94 (C=N), The system was stirred at 80 °C until the reaction was completed
(monitored by TLC, dichloromethane). The precipitated solid was
28.37, 128.00, 127.19, 122.12, 120.48, 50.92, 41.64, 35.59, 11.37; filtered off, washed with ice water and ethanol to afford target
60.41 (quinazolinone‐4‐C), 153.80, 148.98, 143.38, 140.74,
+
HRMS (ESI) calcd. for C16
45.0574.
Compound (4e): White solid. Yield: 32.8%; m.p. 193—196 °C;
H13ClN
4
OS [M+H] , 345.0577; found,
compound (112 mg) as white solid. Yield: 71.3%; m.p. 234—
1
3
6
235 °C; Purity: 96%; H NMR (600 MHz, DMSO‐d ) δ: 11.38 (d, J =
26.9 Hz, 1H, NH), 8.37 (s, 1H, quinazolinone‐2‐H), 8.16 (d, J = 8.5
Hz, 1H, quinazolinone‐5‐H), 8.05 (d, J = 3.1 Hz, 1H, thiazole‐4‐H),
7.85 (d, J = 3.1 Hz, 1H, thiazole‐5‐H), 7.79 (d, J = 1.5 Hz, 1H,
quinazolinone‐8‐H), 7.61 (dd, J = 8.5, 1.7 Hz, 1H, quinazolinone‐6‐
H), 6.98 (t, J = 7.7 Hz, 2H, phenyl‐3,5‐H), 6.92 (d, J = 7.8 Hz, 2H,
1
Purity: 99%; H NMR (600 MHz, CDCl
none‐2‐H), 8.21 (d, J = 8.6 Hz, 1H, quinazolinone‐5‐H), 7.81 (d, J =
.1 Hz, 1H, thiazole‐4‐H), 7.67 (d, J = 1.4 Hz, 1H, quinazolinone‐8‐
H), 7.45—7.41 (m, 1H, quinazolinone‐6‐H), 7.31 (d, J = 3.1 Hz, 1H,
thiazole‐5‐H), 5.38 (s, 2H, CH ), 3.78—3.73 (m, 1H, CH), 1.15—
.10 (m, 2H, cyclopropylimino‐CH ), 1.07 (d, J = 2.9 Hz, 2H, cyclo‐
); C NMR (151 MHz, CDCl ) δ: 170.01, 160.16,
3
) δ: 8.61 (s, 1H, quinazoli‐
3
2
phenyl‐2,6‐H), 6.80 (t, J = 7.1 Hz, 1H, phenyl‐4‐H), 5.16 (s, 2H, CH
2
);
1
3
1
2
C NMR (151 MHz, DMSO‐d ) δ: 160.14, 159.39, 153.84, 148.95,
6
1
3
propylimino‐CH
2
3
142.89, 139.03, 128.36, 128.29, 127.33, 126.41, 126.30, 121.44,
1
1
52.83, 149.08, 148.86, 143.25, 140.59, 128.16, 127.85, 127.05,
22.30, 120.33, 62.40, 50.79, 41.87, 34.90, 34.78, 24.95, 24.56;
+
+
HRMS (ESI) calcd. for C18
3
H17ClN
4
OS [M+H] , 373.0890; found,
73.0890.
Compound (5a): To a mixture of intermediate 3a (100 mg,
.33 mmol) and phenylhydrazine (71 mg, 0.66 mmol) in ethanol
was added hydrochloric acid. The system was stirred at 80 °C until
2
the reaction was completed (monitored by TLC, dichloromethane). 1H, quinazolinone‐6‐H), 5.47 (s, 2H, CH ); C NMR (151 MHz,
1H, quinazolinone‐2‐H), 8.15 (d, J = 8.4 Hz, 1H, quinazolinone‐5‐H),
8.13 (d, J = 3.2 Hz, 1H, thiazole‐4‐H), 8.09—8.07 (m, 1H, thia‐
zole‐5‐H), 7.77 (s, 1H, quinazolinone‐8‐H), 7.59 (dd, J = 8.5, 2.0 Hz,
0
1
3
The precipitated solid was filtered off, washed with ice water and
DMSO‐d
6
) δ: 163.69, 159.99, 153.23, 150.73, 144.37, 142.75,
ethanol to afford target compound (79 mg) as yellow solid. Yield:
139.58, 128.65, 127.89, 126.85, 124.98, 120.92, 46.82; HRMS (ESI)
1
+
6
1.0%; m.p. 228—229 °C; Purity: 98%; H NMR (600 MHz, CDCl
3
) δ: calcd. for C13
H
9
ClN
4
O
2
S [M+H] , 321.0213; found, 321.0204.
1
3.31 (s, 1H, NH), 8.36 (s, 1H, quinazolinone‐2‐H), 8.25 (d, J = 8.5
Compound (7a): Compound 6 (200 mg, 0.62 mmol) and po‐
tassium carbonate (171 mg, 1.24 mmol) were stirred in acetoni‐
Hz, 1H, quinazolinone‐5‐H), 7.99 (d, J = 3.1 Hz, 1H, thiazole‐4‐H),
7
1
7
6
.72 (d, J = 1.5 Hz, 1H, quinazolinone‐8‐H), 7.45 (dd, J = 8.5, 1.6 Hz, trile at 50 °C for 0.5 h, then cooled to room temperature for add‐
H, quinazolinone‐6‐H), 7.38 (d, J = 3.2 Hz, 1H, thiazole‐5‐H),
.29—7.26 (m, 2H, Ph‐3,5‐H), 7.16 (d, J = 8.0 Hz, 2H, Ph‐2,6‐H),
ing methyl iodide (176 mg, 1.24 mmol) and continued to reaction
at 50 °C. After the reaction was completed (monitored by TLC,
dichloromethane), acetonitrile was removed and the residue was
extracted with ethyl acetate (3 × 20 mL), dried over anhydrous
sodium sulfate and purified by silica gel column chromatography
(eluent, dichloromethane/petroleum ether, 2/1, V/V) to afford
1
3
.94 (t, J = 7.2 Hz, 1H, Ph‐4‐H), 5.27 (s, 2H, CH
) δ: 161.19, 160.50, 149.20, 147.68, 143.62, 143.24,
40.78, 129.49, 128.56, 128.08, 127.34, 124.44, 122.11, 120.63,
2
); C NMR (151
MHz, CDCl
3
1
1
3
+
18.65, 113.97, 48.46; HRMS (ESI) calcd. for C19
96.0686; found, 396.0686.
5
H14ClN OS [M+H] ,
desirable product (137 mg) as white solid. Yield: 65.6%; m.p.
1
Compound (5b): Yellow solid. Yield: 60.7%; m.p. > 250 °C; Pu‐
177—178 °C; Purity: 97%; H NMR (600 MHz, DMSO‐d
6
) δ: 8.55 (s,
1
rity: 98%; H NMR (600 MHz, DMSO‐d
6
) δ: 12.39 (s, 1H, NH), 8.96
1H, quinazolinone‐2‐H), 8.15 (d, J = 7.9 Hz, 3H, quinazolinone‐5‐H,
(
d, J = 2.4 Hz, 1H, (2,4‐dinitrophenyl)hydrazineylidene‐3‐H), 8.81 (s, thiazole‐4‐H, thiazole‐5‐H), 7.79 (s, 1H, quinazolinone‐8‐H), 7.60
1
H, quinazolinone‐2‐H), 8.56 (dd, J = 9.4, 2.3 Hz, 1H, (2,4‐dinitro‐
(d, J = 8.5 Hz, 1H, quinazolinone‐6‐H), 5.47 (s, 2H, CH
CH ); C NMR (151 MHz, DMSO‐d
3 6
2
), 3.95 (s, 3H,
) δ: 159.38, 152.37, 150.07,
149.01, 144.65, 142.58, 139.08, 128.18, 127.33, 126.38, 125.28,
1
3
phenyl)hydrazineylidene‐5‐H), 8.13 (d, J = 8.6 Hz, 1H, (2,4‐dinitro‐
phenyl)hydrazineylidene‐6‐H), 8.01—7.98 (m, 2H, quinazoli‐
none‐5‐H, thiazole‐4‐H ), 7.88 (d, J = 3.0 Hz, 1H, quinazolinone‐
+
120.26, 63.12, 46.16; HRMS (ESI) calcd. for C14
335.0369; found, 335.0363.
4 2
H11ClN O S [M+H] ,
6
‐H), 7.78 (s, 1H, quinazolinone‐8‐H), 7.58 (d, J = 8.6 Hz, 1H, thia‐
zole‐5‐H), 5.38 (s, 2H, CH ). HRMS (ESI) calcd. for C19
M+H] , 486.0387; found, 486.0379.
Compound (5c): Yellow solid. Yield: 82.7%. m.p. > 250 °C; Pu‐
2
H12ClN
7
5
O S
Compound (7b): White solid. Yield: 74.5%; m.p. 153—154 °C;
Purity: 99%; H NMR (600 MHz, CDCl ) δ: 8.34 (s, 1H, quinazoli‐
3
+
1
[
none‐2‐H), 8.26 (d, J = 5.7 Hz, 1H, quinazolinone‐5‐H), 7.99 (d, J =
3.2 Hz, 1H, thiazole‐4‐H), 7.70 (d, J = 1.9 Hz, 1H, quinazoli‐
none‐8‐H), 7.59 (d, J = 3.2 Hz, 1H, thiazole‐5‐H), 7.43 (dd, J = 3.6,
1
rity: 97%; H NMR (600 MHz, DMSO‐d
6
) δ: 12.22 (s, 1H, NH), 8.88
(s, 2H, isonicotinohydrazide‐2,6‐H), 8.78 (s, 1H, quinazolinone‐
2
‐H), 8.18 (d, J = 8.2 Hz, 1H, quinazolinone‐5‐H), 7.98 (s, 3H, isoni‐
2.0 Hz, 1H, quinazolinone‐6‐H), 5.45 (s, 2H, CH ), 4.36 (q, J = 7.1
2
13
cotinohydrazide‐3,5‐H, quinazolinone‐8‐H), 7.85 (s, 1H, thiazole‐
‐H), 7.77 (s, 1H, quinazolinone‐6‐H), 7.60 (d, J = 8.5 Hz, 1H, thia‐
zole‐5‐H), 5.52 (s, 2H, CH ). HRMS (ESI) calcd. for C19
M+H] , 425.0587; found, 425.0593.
Compound (5d): White solid. Yield: 56.3%; m.p. 223—225 °C;
Hz, 2H, OCH
CDCl ) δ: 160.33, 153.40, 148.76, 144.05, 143.33, 142.42, 140.45,
128.41, 127.80, 127.73, 126.93, 123.51, 120.68, 71.99, 46.86,
2 3
), 1.36 (t, J = 7.1 Hz, 3H, CH ); C NMR (151 MHz,
4
3
2
6 2
H13ClN O S
+
+
[
14.50; HRMS (ESI) calcd. for C15
found, 349.05203.
4 2
H14ClN O S [M+H] , 349.0526;
1
Purity: 99%; H NMR (600 MHz, DMSO‐d
6
) δ: 12.20 (d, J = 36.5 Hz,
Compound (7c): White solid. Yield: 54.0%; m.p. 172—173 °C;
1
1H, NH), 8.54 (s, 1H, quinazolinone‐2‐H), 8.22 (d, J = 2.6 Hz, 1H,
3
Purity: 96%; H NMR (600 MHz, CDCl ) δ: 8.26 (s, 1H, quinazoli‐
quinazolinone‐5‐H), 8.19 (d, J = 8.5 Hz, 1H, thiazole‐4‐H), 8.16 (d,
J = 2.7 Hz, 1H, thiazole‐5‐H), 7.87 (s, 1H, quinazolinone‐8‐H), 7.63
none‐2‐H), 8.21 (d, J = 8.6 Hz, 1H, quinazolinone‐5‐H), 7.85 (d, J =
3.0 Hz, 1H, quinazolinone‐8‐H), 7.70 (d, J = 1.5 Hz, 1H, thiazole‐4‐
H), 7.44 (dd, J = 8.6, 1.7 Hz, 1H, quinazolinone‐6‐H), 7.33 (d, J = 3.2
(d, J = 8.5 Hz, 1H, quinazolinone‐6‐H), 7.26 (t, J = 7.6 Hz, 4H, di‐
phenyl‐3,5‐H), 7.17 (t, J = 7.3 Hz, 2H, diphenyl‐4‐H), 6.95 (d, J = 7.8
Hz, 1H, thiazole‐5‐H), 5.35 (s, 2H, CH
2
), 4.27 (t, J = 6.6 Hz, 2H,
CH ), 1.50—1.42 (m, 2H,
), 0.88 (t, J = 7.4 Hz, 3H, CH
) δ: 162.74, 160.10, 148.83, 148.79, 148.53, 147.58, 143.31,
1
3
Hz, 4H, diphenyl‐2,6‐H), 5.36 (s, 2H, CH
2
); C NMR (151 MHz,
OCH
2
), 1.68—1.62 (m, 2H, OCH
CH CH
2
2
1
3
DMSO‐d ) δ: 159.47, 158.72, 149.77, 149.52, 149.48, 149.16,
6
OCH
2
2
2
3
); C NMR (151 MHz,
1
1
C
43.40, 139.24, 129.74, 128.22, 127.48, 126.52, 125.41, 122.82,
CDCl
3
20.34, 120.14, 120.11, 47.63; HRMS (ESI) calcd. for
140.49, 128.25, 128.13, 128.06, 127.82, 126.91, 126.88, 120.57,
+
25
H19ClN
5
O
4
S [M+H] , 552.0662; found, 552.0656.
76.08, 50.78, 31.00, 30.74, 18.91, 13.68; HRMS (ESI) calcd. for
+
Compound (5e): To a mixture of intermediate 3a (100 mg,
C
17
H17ClN
4
O
2
S [M+H] , 377.0839; found, 377.0839.
1100
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Chin. J. Chem. 2021, 39, 1093-1103