˘
1
150
W. Fathalla, M.Cajan, J. Marek and P. Pazdera
Vol. 39
(
NCH ), 48.55 (NCH ), 26.53 (CH ), 25.92 (CH ), 24.82 (CH );
(CHAr), 128.15 (CHAr), 127.83 (CH ), 120.59 (CHAr), 112.57
2
2
2
2
2
Ar
+
+
Ms: m/z 348 (M ), 264, 263, 206, 205, 132, 103, 102, 85, 84, 77,
7
(C ), 51.31 (NCH ); ms: m/z 370 (M ), 339, 337, 264, 263, 239,
q
2
6, 75, 56.
Anal. Calcd. for C20H N S (348.47): C 68.94; H 5.78; N
222, 221, 206, 205, 149, 118, 104, 102, 91, 77, 65, 51.
Anal. Calcd. for C22H18N S (370.47): C 71.33; H 4.90; N
20
4
4
1
6.08; S 9.20. Found: C 68.79; H 5.70; N 16.10; S 9.09.
15.12; S 8.65. Found: C 71.24; H 4.88; N 15.03; S 8.59.
Pyrrolidine-1-carbothioic Acid (2-Phenyl-3H-quinazolin-4-
ylidene) Amide (2b).
1
-Cyclohexyl-3-(2-phenylquinazolin-4-yl)thiourea (3c).
Compound 3c (NH R=cyclohexylamine) was obtained in 77%
2
Compound 2b (NHRR=pyrrolidine) was obtained in 66%
yield (0.81 g); mp 154-155 °C; ir: 3441, 3425 (NH), 1619 (C=N)
yield (0.69 g); mp 205-206 °C; ir: 3200 (NH), 2968, 2867 (CH),
cm ; 1H nmr: d 12.08 (1H, b, NHCH), 8.75 (1H, s, NH),
.32-7.54 (9H, m, ArH), 4.28-4.38 (1H, m, NHCH), 2.34-2.27
(2H, m, CH2), 1.91-1.71 (4H, m, 2CH2), 1.55-1.38 (4H, m,
-1
-
1 1
1
611 (C=N) cm ; H nmr: d 8.45–7.44 (9H, m, ArH), 4.01 (2H,
8
t, NCH ) (J = 6.90 Hz), 3.87 (2H, t, NCH ) (JA,B= 6.90 Hz),
2
A,B
2
1
3
1
.99-2.07 (4H, m, CH2); C nmr: d 183.19 (C=S), 155.66 (C2),
2
1
CH ); 13C nmr: d 178.54 (C=S), 158.90 (C ), 156.07 (C ),
1
51.04 (C ), 149.18 (C ), 134.72 (CH ), 133.17 (CH ), 132.11
2
q
q
4
q
Ar
Ar
51.45 (C ), 137.69 (C ), 134.55 (CH ), 131.15 (CH ), 129.77
(
(
CH ), 129.68 (CHAr), 128.59 (CHAr), 128.02 (CH ), 127.34
q
q
Ar
Ar
Ar
Ar
CHAr), 125.96 (CHAr), 121.84 (C ), 52.21 (NCH ), 51.69
(CHAr), 128.92 (CHAr), 128.40 (CHAr), 127.80 (CHAr), 120.65
(CHAr), 112.66 (C ), 55.49 (CH), 32.78 (CH ), 32.78 (CH ),
q
2
+
(
NCH ), 27.05 (CH ), 26.31 (CH ); Ms: m/z 334 (M ), 301, 265,
2
2
2
q
2
2
2
64, 263, 232, 206, 205, 103, 102, 77, 70.
25.87(CH ), 25.17(CH ).
Anal. Calcd. for C21H N S (362.49): C 69.58; H 6.12; N
22 4
2
2
Anal. Calcd. for C19H18N S (334.44): C 68.24; H 5.42; N
4
1
6.75; S 9.59. Found: C 68.07; H 5.33; N 16.60; S 9.43.
1
5.46; S 8.84. Found: C 69.41; H 6.12; N 15.38; S 8.74.
4
-Methylpiperazine-1-carbothioic Acid (2-Phenyl-3H-quina-
1
-Phenyl-3-(2-phenylquinazolin-4-yl)thiourea (3d).
zolin-4-ylidene) Amide (2c).
Compound 3d (NH R=aniline) was obtained in 43% yield
2
Compound 2c (NHRR=N-methylpiperazine) was obtained in
-1
(
0.35 g); mp 165-166 °C; ir: 3436, 3418 (NH), 1617 (C=N) cm ;
1H nmr: d 14.26 (1H, s, NHPh), 8.93 (1H, s, NH), 8.35-7.29
14H, m, ArH); 13C nmr: d 178.62 (C=S), 158.57 (C ), 155.96
5
1
4
3% yield (0.54 g); mp 244-245 °C; ir: 3240 (NH), 2934 (CH),
-
1 1
610 (C=N) cm ; H nmr: d 8.43–7.48 (9H, m, ArH), 4.42-
(
.37 (4H, m, NCH ), 2.60-2.56 (4H, m, NCH ), 2.39 (3H, s,
q
2
2
1
3
(C ), 151.64 (C ), 144.85(C ), 138.49 (C ), 137.36 (C ), 134.85
CH3); C nmr: d 184.38 (C=S), 154.85 (C ), 149.51 (C ),
q q q q q
2
4
(
CH ), 131.31 (CHAr), 129.93 (CH ), 129.24 (CH ), 128.39
Ar Ar Ar
1
1
1
4
3
7
49.13 (C ), 134.73 (CHAr), 132.86 (CHAr), 132.00 (CHAr),
q
29.37 (CHAr), 128.43 (CHAr), 127.60 (CHAr), 127.34 (CHAr),
(CHAr), 128.03 (CHAr), 126.88 (CHAr), 124.13 (CHAr), 120.65
+
25.65 (CHAr), 121.51 (C ), 55.06 (NCH ), 54.71(NCH ),
(CHAr), 112.62 (C ); ms: m/z 356 (M ), 323, 276, 264, 263, 222,
q
2
2
q
7.21 (CH NCH ), 46.78 (CH NCH ), 45.53 (NCH ); ms: m/z
221, 205, 178, 135, 118, 104, 102, 93, 91, 77, 51.
3
2
3
2
3
+
63 (M ), 264, 263, 206, 205, 131, 103, 102, 100, 99, 83, 77,
5, 74, 70, 58, 56.
Anal. Calcd. for C21H16N S (356.44): C 70.76; H 4.52; N
4
1
5.72; S 8.99. Found: C 70.58; H 4.52; N 15.64; S 8.83.
-(4-Methylphenyl)-3-(2-phenylquinazolin-4-yl)thiourea (3e).
Compound 3e (NH2R=p-toluidine) was obtained in 38%
Anal. Calcd. for C20H N S (363.48): C 66.09; H 5.82; N
21
5
1
1
9.27; S 8.82. Found: C 65.90; H 5.70; N 19.07; S 8.69.
1
-Butyl-3-(2-phenylquinazolin-4-yl)thiourea (3a).
yield (0.31 g); mp 179-180 °C; ir: 3422 (NH), 1619 (C=N)
Compound 3a (NH R=butylamine) was obtained in 60% yield
2
cm ; 1H nmr: d 14.16 (1H, s, NHPh), 8.92 (1H, s, NH),
-1
(
1
8
(
(
0.58 g); mp 165-166 °C; ir: 3427 (NH), 2952, 2928, 2869 (CH),
8
.36-7.29 (13H, m, ArH), 2.40 (3H, s, CH ); 13C nmr:
-
1 1
3
618 (C=N) cm ; H nmr:d 12.16 (1H, s, NH), 8.79 (1H, s, NH),
d 178.62 (C=S), 158.57 (C ), 155.99 (C ), 151.52 (C ),
.24-7.48 (9H, m, ArH), 3.79-3.75 (2H, m, NHCH ), 1.83-1.76
q
q
q
2
1
44.85(C ), 138.49 (C ), 137.30 (C ), 136.83 (C ), 134.84
2H, m, NCH CH ), 1.49-1.42 (2H, m, HNCH CH CH ), 0.94
q q q q
2
2
2
2
2
1
3
(CHAr), 131.32 (CHAr), 129.82 (CHAr), 129.09 (CHAr),
128.38 (CHAr), 128.03 (CH Ar), 124.18 (CH Ar), 120.67
3H, t, CH CH ) (JA,B= 7.31 Hz); C nmr: d 180.11 (C=S),
2 3
1
58.90 (C ), 156.16 (C ), 151.57 (C ), 137.70 (C ), 134.57
q q q q
(
(
(
CH ), 131.18 (CH ), 129.89 (CH ), 128.93 (CHAr), 128.38
(CHAr), 112.63 (C ), 21.33 (CH ); ms: m/z 337, 264, 263,
222, 221, 206, 205, 149, 148, 118, 107, 106, 91, 77.
Ar
Ar
Ar
q 3
CHAr), 127.81 (CHAr), 120.67 (CHAr), 112.70 (C ), 46.55
q
NCH ), 31.05 (NCH CH ), 20.60 (HNCH CH CH ), 13.99
Anal. Calcd. for C22H18N S (370.47): C 71.33; H 4.90; N
2
2
2
2
2
2
4
+
(
CH ); ms: m/z 336 (M ), 304, 303, 264, 247, 222, 221, 206, 205,
3
15.12; S 8.65. Found: C 71.21; H 4.89; N 15.11; S 8.62.
1
30, 118, 104, 102, 77, 72, 41.
Anal. Calcd. for C H N S (336.45): C 67.83% ; H 5.99; N
1
-(4-Methoxyphenyl)-3-(2-phenylquinazolin-4-yl)thiourea (3f).
Compound 3f (NH R=p-anisidine) was obtained in 40% yield
1
9 20 4
1
6.65; S 9.53. Found: C 67.64; H 5.81; N 16.48; S 9.43.
2
1
-Benzyl-3-(2-phenylquinazolin-4-yl)thiourea (3b).
(0.34 g); mp 168-169 °C; ir: 3428 (NH), 2934 (CH), 1616 (C=N)
-
1 1
cm ; H nmr:d 14.09 (1H, s, NHPh), 8.91 (1H, s, NH), 8.35-6.98
13H, m, ArH), 3.86 (3H, s, OCH ); 13C nmr: d 178.78 (C=S),
Compound 3b (NH R=benzylamine) was obtained in 68%
2
(
3
yield (0.72 g); mp 189-190 °C; ir: 3292 (NH), 3024 (CH), 1619
-
1
1
158.39 (Cq), 155.98 (Cq), 152.49 (Cq), 151.55 (Cq), 141.78 (Cq),
37.32 (C ), 134.86 (CH ), 131.45(C ), 131.32 (CHAr), 129.87
(C=N) cm ; H nmr: d 12.31 (1H, s, NHCH ), 8.88 (1H, s, NH),
2
1
8
.03-7.18 (14H, m, ArH), 4.98 (2H, d, NHCH ) (JA,B= 4.66 Hz);
q
Ar
q
2
1
3
(CH ), 129.09 (CHAr), 128.35 (CHAr), 128.03 (CH ), 125.78
C nmr: d 179.82 (C=S), 158.90 (C ), 156.00 (C ), 151.36 (C ),
Ar Ar
q
q
q
1
36.89 (C ), 136.49 (C ), 134.62 (CH ), 130.94 (CH ), 129.77
(CHAr), 120.67 (CHAr), 114.48 (CHAr), 113.45 (Cq), 112.63 (Cq),
55.75 (OCH3).
q
q
Ar
Ar
(
CHAr), 129.37 (CHAr), 129.20 (CHAr), 128.85 (CHAr), 128.59