SOMMAIRE

J.MAR.CHIM.HETEROCYCL. Volume 1, N° 1 Décembre 2002
RMN 1 H (DMSO-d6) : 2.26 (s, 3H, CH3); 5.10 (d, 1H, J = 5.5 Hz, CH) ; 6.51-8.50 (m, 12H, Ar);
9.20 (d, 1H, exchangeable with D2O, J = 5.5 Hz, NH); 12.4 (s, 1H, exchangeable with D2O,
NHCO).
HRMS calc. for C23H23N4O3 m/z : cal. : 403.1770 (M+H)+; found : 403.1776 (M+H)+.
3b: IR (Nujol) : νCO = 1654, 1684, 1690 cm- 1
; νNH = 3250-3412 cm- 1
RMN 1 H (DMSO-d6) : 5.29 (s, 1H, CH); 6.55-8.47 (m, 16H, Ar); 9.29.(s, 1H, exchangeable with
D2O, NH); 12.38 (s, 1H, exchangeable with D2O, NHCO).
RMN 13 C (DMSO-d6) : 61.58 (dm, 1 J = 140.8 Hz, CHN); 112.5, 116.8, 122.9, 125.8, 127.4, 128.6,
129.9, 130.5, 139.8, 142.6 (Ar-ring C); 169.14 (m, CO) 170.38 (m, CO) 171.24 (m, CO).
3c: IR (Nujol) : νCO = 1645, 1655, 1696 cm- 1
; νNH = 3200-3497 cm- 1
RMN 1 H (DMSO-d6) : 5.18 (s, 1H, CH); 6.59-8.65 (m, 16H, Ar); 9.28 (br, 1H, NH); 12.45 (s, 1H,
NHCO).
RMN 13 C (DMSO-d6) : 62.72 (dm, 1
J = 141.3 Hz, CHN); 112.6, 116.7, 122.7, 125.6, 127.6, 128.8,
129.8, 130.6, 139.9, 147.8 (Ar-ring C); 169.72 (m, CO), 170.42 (m, CO), 171.25 (m, CO).
Quinazolin-4-ones 4
General procedure :
Gem-dicyano epoxides 1 (5 mmol) and anthranilamide 2 (5 mmol) are heated under reflux in
acetonitrile (40 mL) for 20 hours. After evaporation of the solvent under reduced pressure, the
residue is treated with ethyl ether / acetone (4 : 1). The precipitated product 4 is recrystallised.
1,2,3,4-tertrahydro 2-(p-tolyl) quinazolin-4-one 4a
IR (Nujol) : νCO = 1672, 1678 cm- 1
; νNH = 3280-3490 cm- 1
RMN 1 H (DMSO-d6) : 2.30 (s, 3H, CH3); 3.45 (s, 1H; NH); 5.75 (s, 1H, CH); 6.67-7.67 (m, 8H,
Ar); 8.28 (s, 1H, NHCO).
RMN 13 C (DMSO-d6) : 20.65 (CH3); 66.37 (CHN); 113.5, 116.9, 122.5, 125.6, 127.8, 128.4, 129.5,
130.2, 139.9, 142.2 (Ar-ring C); 163.66 (broad s, CO)
HRMS calc. for C15H14N2O m/z : cal : 237.1028 (M-H)+; found : 237.102 (M-H)+.
C15H14N2O : Calc. C 75.32 H 6.03 N 11.40
Found 75.05 5.91 11.38
1,2,3,4-tertrahydro 2-(4-chloro phenyl) quinazolin-4-one 4b
IR (Nujol) : νCO = 1683, 1688 cm- 1
; νNH = 3257-3460 cm- 1
RMN 1 H (DMSO-d6) : 1.90 (s, 1H, NH); 4.80 (s, 1H, CH); 7.16-7.81 (m, 8H, Ar); 7.99 (s, 1H,
NHCO).
RMN 13 C (DMSO-d6) : 56.50 (CHN); 113.2, 115.8, 121.9, 124.8, 126.4, 128.6, 129.9, 130.5,
139.8, 146.4 (Ar-ring C) ; 164.24 (CO).
3-aryl quinoxalin-2-one 8
General procedure :
Gem-dicyano epoxides 1 (5 mmol) and o-phenylenediamine 8 (5 mmol) are heated under
reflux in acetonitrile (40 mL) for 16 hours. After evaporation of the solvent under reduced pressure,
the residue is treated with ethyl ether / petroleum ether (4 : 1). The precipitated product 8 is filtered
by column alumina (eluent : acetone) and recrystallised.
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