1978
H. Yassine et al.
Paper
Synthesis
Dibutyl 2,2′-[Carbonylbis(azanediyl)]dibenzoate (6e)
1H NMR (400 MHz, DMSO-d6): = 9.85 (s, 1 H, NH), 8.25 (d, J = 8 Hz, 1
H, Ar-H), 8.13 (d, J = 8 Hz, 1 H, ArH), 7.72 (t, J = 8 Hz, 1 H, ArH), 7.52–
7.60 (m, 2 H, ArH), 7.37 (d, J = 8 Hz, 1 H, ArH), 7.22 (t, J = 4 Hz, 1 H,
ArH), 6.94 (d, J = 8 Hz, 1 H, ArH), 4.10–4.22 (m, 2 H, CH2), 1.11 (t, J = 8
Hz 3 H, CH3).
13C NMR (100 MHz, DMSO-d6): = 164.6 (COO), 162.8 (C=O), 151.8
(C=O), 138.9 (C), 135.4 (C), 135.2 (CH), 133.5 (CH), 132.1 (CH), 130.6
(CH), 129.2 (CH), 128.5 (C), 128.3 (CH), 123.4 (CH), 115.4 (CH), 114.8
(C), 61.3 (OCH2), 13.8 (CH3).
White solid; yield: 55 mg (30%, 0.13 mmol); mp 88–90 °C (hexane).
1H NMR (300 MHz, DMSO-d6): = 10.82 (s, 2 H, NH), 8.54 (d, J = 8.4
Hz, 2 H, ArH), 8.04 (d, J = 8.1 Hz, 2 H, ArH), 7.52 (t, J = 8.4 Hz, 2 H, ArH),
7.01 (t, J = 8.1 Hz, 2 H, ArH), 4.36 (t, J = 6.6 Hz, 4 H, CH2), 1.54–1.55 (m,
4 H, CH2), 1.43–1.58 (m, 4 H, CH2), 0.99 (t, J = 7.5 Hz, 6 H, CH3).
13C NMR (75 MHz, DMSO-d6): = 167.9, 152.1, 142.6, 134.2, 130.8,
121.1, 121.1, 119.6, 115.0, 68.9, 21.9.
HMRS (ESI): m/z [M + H] calcd for C23H29N2O5: 413.2076; found:
413.2074.
HMRS (ESI): m/z [M + H] calcd for C17H15N2O4: 311.1032; found:
311.1029.
Diallyl 2,2′-[Carbonylbis(azanediyl)]dibenzoate (6f)
Propyl 2-[2,4-Dioxo-1,2-dihydroquinazoline-3(4H)-yl]benzoate
(9c)
Beige solid; yield: 60 mg (35%, 0.16 mmol); mp 85–87 °C (hexane).
1H NMR (400 MHz, CDCl3): = 10.75 (s, 2 H, NH), 8.55 (d, J = 8 Hz, 2 H,
ArH), 8.07 (d, J =12 Hz, 2 H, ArH), 7.54 (t, J = 8 Hz, 1 H, ArH), 7.03 (t, J =
12 Hz, 2 H, ArH), 6.03–5.89 (m, 2 H), 5.43 (d, J = 16 Hz, 2 H), 5.32 (d, J =
4 Hz, 2 H, 2 × CH), 4.86 (d, J = 4 Hz, 4 H, 2 × CH2).
13C NMR (100 MHz, CDCl3): = 168.2, 152.1, 142.8, 134.7, 131.9,
131.0, 121.4, 119.8, 118.8, 114.4, 65.9.
White solid; yield: 79 mg (94%, 0.24 mmol); mp 260–262 °C (hexane).
1H NMR (400 MHz, DMSO-d6): = 9.82 (s, 1 H, NH), 8.25 (d, J = 8 Hz, 1
H, ArH), 8.13 (d, J = 8 Hz, 1 H, ArH), 7.72 (t, J = 8 Hz, 1 H, ArH), 7.53–
7.62 (m, 2 H, ArH), 7.37 (d, J = 8 Hz, 1 H, ArH), 7.22 (t, J = 8 Hz, 1 H,
ArH), 6.94 (d, J = 8 Hz, 1 H, ArH), 4.07 (t, J = 8 Hz, 2 H, OCH2), 1.46–1.58
(m, 2 H, CH2), 0.84 (t, J = 8 Hz, 3 H, CH3).
HMRS (ESI): m/z [M + H] calcd for C21H21N2O5: 381.1450; found:
381.1455.
HMRS (ESI): m/z [M + H] calcd for C18H17N2O4: 325.1188; found:
325.1191.
Di(prop-2-yn-1-yl) 2,2′-[Carbonylbis(azanediyl)]dibenzoate (6g)
Isopropyl 2-[2,4-Dioxo-1,2-dihydroquinazoline-3(4H)-yl]benzo-
Beige solid; yield: 85 mg (50%, 0.22 mmol); mp 178–180 °C (hexane).
ate (9d)
1H NMR (400 MHz, DMSO-d6): = 10.1 (s, 2 H, NH), 8.07 (d, J = 8 Hz, 2
H, ArH), 7.89 (d, J = 8 Hz, 2 H, ArH), 7.60 (t, J = 8 Hz, 2 H, ArH), 7.15 (t,
J = 8 Hz, 2 H, ArH), 4.95 (d, J =2.4 Hz, 4 H, 2 × CH2), 3.60 (t, J = 2.4 Hz, 2
H, 2 × CH).
13C NMR (100 MHz, DMSO-d6): = 170.3, 166.3, 152.0, 140.5, 134.0,
130.4, 122.2, 121.2, 117.2, 78.1, 78.1, 59.7.
White solid; yield: 67 mg (80%, 0.21 mmol); mp 238–240 °C (hexane).
1H NMR (400 MHz, DMSO-d6): = 9.68 (s, 1 H, NH), 8.24 (d, J = 8 Hz, 1
H, ArH), 8.14 (d, J = 8 Hz, 1 H, ArH), 7.71 (t, J = 8 Hz, 1 H, ArH), 7.58 (t,
J = 8 Hz, 2 H, ArH), 7.30 (d, J = 8 Hz, 1 H, ArH), 7.23 (t, J = 8 Hz, 1 H,
ArH), 6.95 (d, J = 8 Hz, 1 H, ArH), 4.10–4.22 (m, 1 H, CH), 1.10 (d, J = 8
Hz, 6 H, 2 × CH3).
HMRS (ESI): m/z [M + H] calcd for C18H17N2O4: 325.1188; found:
HMRS (ESI): m/z [M + H] calcd for C21H17N2O5: 377.1137; found:
325.1189.
377.1141.
Butyl 2-[2,4-Dioxo-1,2-dihydroquinazoline-3(4H)-yl]benzoate (9e)
Alkyl 2-[2,4-Dioxo-1,2-dihydroquinazolin-3(4H)-yl]benzoates 9a–
g; General Procedure
White solid; yield: 70 mg (87%, 0.20 mmol); mp 230–232 °C (hexane).
1H NMR (300 MHz, DMSO-d6): = 11.60 (s, 1 H, NH), 8.04 (d, J = 7.8
Hz, 1 H, ArH), 7.92 (d, J = 9 Hz, 1 H, ArH), 7.66–7.76 (m, 2 H, ArH), 7.59
(t, J = 9 Hz, 1 H, ArH), 7.45 (d, J = 7.8 Hz, 1 H, ArH), 7.22 (t, J = 7.8 Hz, 2
H, ArH), 4.03 (t, J = 6.3 Hz, 2 H, OCH2), 1.10–1.36 (m, 4 H, 2 × CH2),
0.67 (t, J = 7.5 Hz, 3 H, CH3).
13C NMR (75.5 MHz, DMSO-d6): = 165.0 (COO), 162.7 (C=O), 150.5
(C=O), 140.3 (C), 136.1 (C), 135.8 (CH), 133.9 (CH), 131.6 (CH), 131.5
(CH), 129.3 (CH), 128.7 (C), 128.0 (CH), 123.0 (CH), 115.7 (CH), 114.7
(C), 65.1 (OCH2), 30.4 (CH2), 19.1 (CH2), 13.9 (CH3).
To a solution of the respective 2,2′-[carbonylbis(azanediyl)]dimeth-
yldibenzoate 6 (0.37 mmol) in MeCN (10 mL) at reflux was added an
excess of K2CO3 (8 equiv). After stirring for 2 h, the excess of K2CO3
was removed by filtration and the solvent was evaporated under re-
duced pressure. The residue was purified by silica gel column chro-
matography using a mixture of EtOAc/hexane (6:4).
Methyl 2-[2,4-Dioxo-1,2-dihydroquinazoline-3(4H)-yl]benzoate
(9a)
White solid; yield: 85 mg (96%, 0.29 mmol); mp 275–277 °C (EtOAc).
HMRS (ESI): m/z [M + H] calcd for C19H19N2O4: 339.1345; found:
339.1342.
1H NMR (400 MHz, DMSO-d6): = 9.13 (s, 1 H, NH), 8.23 (d, J = 8 Hz, 1
H, ArH), 8.14 (d, J = 8 Hz, 1 H, ArH), 7.72 (t, J = 8 Hz, 1 H, ArH), 7.51–
7.63 (m, 2 H, ArH), 7.37 (d, J = 8 Hz, 1 H, ArH), 7.23 (t, J = 4 Hz, 1 H,
ArH), 7.01 (d, J = 8 Hz, 1 H, ArH), 3.74 (s, 3 H, CH3).
Allyl 2-[2,4-Dioxo-1,2-dihydroquinazoline-3(4H)-yl]benzoate (9f)
White solid; yield: 79 mg (95%, 0.24 mmol); mp 236–238 °C (EtOAc).
HMRS (ESI): m/z [M + H] calcd for C16H13N2O4: 297.0875; found:
297.0872.
1H NMR (400 MHz, DMSO-d6): = 9.53 (s, 1 H, NH), 8.26 (d, J = 8 Hz, 1
H, ArH), 8.13 (d, J = 8 Hz, 1 H, ArH), 7.73 (t, J = 8 Hz, 1 H, ArH), 7.54–
7.63 (m, 2 H, ArH), 7.38 (d, J = 8 Hz, 1 H, ArH), 7.23 (t, J = 8 Hz, 1 H,
ArH), 6.94 (d, J = 8 Hz, 1 H, ArH), 5.83–5.70 (m, 2 H), 5.21 (d, J = 16 Hz,
1 H, =CH), 5.07 (d, J = 8 Hz, 1 H, =CH), 4.60 (d, J = 4 Hz, 2 H, CH2).
Ethyl 2-[2,4-Dioxo-1,2-dihydroquinazoline-3(4H)-yl]benzoate (9b)
White solid; yield: 88 mg (89%, 0.28 mmol); mp 268–270 °C (EtOAc).
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