10
GOK
117.99, 116.01, 41.38 (NHCH2), 31.68 and 26.55 (COCH3),
22.95 (NHCH2CH2), 11.54 (NHCH2CH2CH3); HRMS
(QTOF‐ESI): m/z calcd for C23H23N5O3: 417.1801; found:
418.1886 [M + 1]+.
(d, J = 7.68 Hz, 1H, quinazoline H‐5), 8.20 (br, s, 1H,
NH), 8.09 (d, J = 8.46 Hz, 1H, phenyl H‐6), 8.00‐7.93
(m, 3H, quinazoline H‐6,7 and phenyl H‐4), 7.72‐7.38
(m, 6H, phenyl H‐6 and benzoyl Ar─H), 4.41 (q, J =
7.12 Hz, 2H, OCH2), 3.54 (q, J = 7.42, 2H, NHCH2), 1.72
(hextet, J = 7.20 Hz, 2H, CH2CH2CH3), 1.38 (t, J = 7.11,
3H, OCH2CH3), 1.05 (t, J = 7.43 Hz, 3H, CH2CH2CH3);
13C NMR (75 MHz, CDCl3) δ (ppm): 189.46 (C═O,
ketone), 185.00 (C═O, ester), 164.75 (C═O, amide),
158.06, 155.96, 153.15, 142.52, 138.73, 134.60, 132.49,
130.43, 130.01, 128.79, 128.67, 128.28, 128.04, 127.87,
126.87, 124.30, 121.30, 117.37, 115.37, 61.52 and 61.24
(OCH2), 41.35 (NHCH2), 22.88 (NHCH2CH2), 14.06 and
13.87 (OCH2CH3), 11.51 (NHCH2CH2CH3); HRMS
(QTOF‐ESI): m/z calcd for C29H27N5O4: 509.2063; found:
510.2154 [M + 1]+.
3.22 | 3‐Oxo‐2‐{[3‐(4‐propylcarbamoyl‐
quinazolin‐2‐yl)‐phenyl]‐hydrazono}‐
butyric acid ethyl ester (18)
Synthesized from compound 15 (0.306 g, 1 mmol) and
ethyl acetoacetate (0.130 g, 1 mmol) according to the gen-
eral procedure. The crude product was purified by crystal-
lization from ethanol and dried in vacuo at 70°C. Yield:
0.27 g (60%); mp 161°C‐162°C; IR (v, cm−1): 3309 (NH),
3075 (Ar CH), 2931 (aliphatic CH), 1706 (C═O, ester),
1688 (C═O, ketone), 1650 (C═O, amide), 1613‐1489
1
(C═C and C═N); H NMR (300 MHz, CDCl3) δ (ppm):
ACKNOWLEDGMENTS
14.93 (s, 1H, C═C─OH enol tautomer), 12.95 (s, 1H, Ar‐
NH‐N═ keto tautomer), 9.46 (d, J = 8.55 Hz, 1H,
quinazoline H‐8), 8.53 (s, 1H, phenyl H‐2), 8.39 (d, J =
7.77 Hz, 1H, quinazoline H‐5), 8.27 (br, s, 1H, NH), 8.13
(d, J = 8.41 Hz, 1H, phenyl H‐6), 7.96 (t, J = 7.75 Hz,
1H, quinazoline H‐7), 7.74‐7.57 (m, 3H, quinazoline H‐6
and phenyl H‐4,5), 4.40 (q, J = 7.00 Hz, 2H, OCH2),
3.57 (q, J = 7.67, 2H, NHCH2), 2.64 and 2.58 (s, 3H,
COCH3), 1.78 (hextet, J = 7.20 Hz, 2H, CH2CH2CH3),
1.44 (t, J = 7.08, 3H, OCH2CH3), 1.08 (t, J = 7.39 Hz,
3H, CH2CH2CH3); 13C NMR (75 MHz, CDCl3) δ (ppm):
197.08 (C═O, ketone), 194.33 (C═O, ester), 164.73
(C═O, amide), 157.84, 156.00, 153.04, 142.16, 138.72,
134.56, 129.95, 128.78, 128.63, 127.82, 125.52, 124.75,
121.25, 117.48, 115.40, 61.46 and 60.99 (OCH2), 41.39
(NHCH2), 30.81 and 26.85 (COCH3), 22.96 (NHCH2CH2),
14.36 and 14.13 (OCH2CH3), 11.53 (NHCH2CH2CH3);
HRMS (QTOF‐ESI): m/z calcd for C24H25N5O4:
447.1907; found: 448.1991 [M + 1]+.
We are grateful to the Dumlupinar University Technology
Research Fund for the financial support of this study
through project number 2015/24.
ORCID
REFERENCES AND NOTES
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3.23 | 3‐Oxo‐3‐phenyl‐2‐{[3‐(4‐
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Synthesized from compound 15 (0.306 g, 1 mmol) and
ethylbenzoylacetate (0.192 g, 1 mmol) according to the
general procedure. The crude product was purified by
crystallization from ethanol and dried in vacuo at 70°C.
Yield: 0.29 g (57%); mp 157°C‐158°C; IR (v, cm−1): 3309
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ester), 1670 (C═O, ketone), 1650 (C═O, amide), 1614‐
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(ppm): 13.77 (s, 1H, C═C─OH enol tautomer), 12.90
(s, 1H, Ar─NH─N═ keto tautomer), 9.45 (d, J = 8.60
Hz, 1H, quinazoline H‐8), 8.40 (s, 1H, phenyl H‐2), 8.30
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