CONDENSATION OF ISATOIC ANHYDRIDE WITH HETARYLGUANIDINES
1149
8.15 m (8H, Harom); 9.50 br.s, 9.92 br.s, 11.95 br.s
(3H, NH). Found, %: C 64.05; H 4.86; N 26.52.
C17H16N6O. Calculated, %: C 63.75; H 5.00; N 26.25.
(DMSO-d6 CCl4), , ppm: 7.15 8.05 m (8H, Harom),
12.41 br.s (1H, NH), 12.55 br.s (1H, OH). Found, %:
C 64.85; H 3.56; N 20.02. C15H10N4O2. Calculated,
%: C 64.75; H 3.60; N 20.14.
4-Hydroxy-2-(4-methylquinazolin-2-ylamino)-
quinazoline (IV). a. A mixture of 3.2 g of compound
III and 15 ml of DMF was heated for 30 min under
reflux. After cooling, the colorless product was filtered
off and recrystallized from chloroform. Yield 2.10 g
2-(1,3-Benzothiazol-2-ylamino)-4-hydroxyquina-
zoline (VIIb). A mixture of 1.92 g of compound Vb
and 1.63 g of isatoic anhydride (I) in 15 ml of DMF
was heated for 5 h under reflux. The mixture was
cooled, and the precipitate was filtered off and recrys-
tallized from DMF. Yield 2.09 g (71%), colorless
crystals melting above 330 C. 1H NMR spectrum
(DMSO-d6), , ppm: 7.23 8.10 m (8H, Harom),
12.38 br.s (1H, NH), 12.66 br.s (1H, OH). Found, %:
C 60.90; H 3.31; N 19.63; S 10.95. C15H10N4OS.
Calculated, %: C 61.22; H 3.40; N 19.05; S 10.88.
1
(70%), colorless needles, mp 295 C. H NMR spec-
trum (DMSO-d6), , ppm: 2.80 s (3H, CH3), 6.40
8.12 m (8H, Harom), 11.06 br.s (1H, NH), 13.38 br.s
(1H, OH). Found, %: C 66.93; H 4.48; N 23.15.
C17H13N5O. Calculated, %: C 67.33; H 4.29; N 23.10.
b. A mixture of 2.01 g of compound II and 1.50 g
of anthranilic acid in 15 ml of DMF was heated for
8 10 h under reflux. After cooling, the precipitate
was filtered off and recrystallized from chloroform.
Yield 2.24 g (75%), colorless crystals, mp 295 C.
1H NMR spectrum (DMSO-d6), , ppm: 2.82 s (3H,
CH3), 6.41 8.08 m (8H, Harom), 11.02 br.s (1H, NH),
13.48 br.s (1H, OH). Found, %: C 66.85; H 4.56;
N 23.52. C17H13N5O. Calculated, %: C 67.33; H 4.29;
N 23.10.
2-[1,3-Benzoxa(thia)zol-2-ylamino]-1-methyl-1,4-
dihydroquinazolin-4-ones IXa and IXb were syn-
thesized as described above for compounds VIIa and
VIIb using N-methylisatoic anhydride (VIII) instead
of isatoic anhydride (I).
Compound IXa. Yield 1.74 g (54%), mp 296 C.
1H NMR spectrum (DMSO-d6), , ppm: 3.78 d (3H,
NCH3), 6.55 8.15 m (8H, Harom), 13.21 d (1H, NH).
Found, %: C 66.88; H 5.56; N 18.02. C18H18N4O2.
Calculated, %: C 67.08; H 5.59; N 17.39.
N-Anthraniloyl-N -(2-benzoxazolyl)guanidine
(VIa). A mixture of 1.76 g of compound Va and
1.63 g of isatoic anhydride (I) in 15 ml of dioxane
was heated for 10 h under reflux. The precipitate was
filtered off and recrystallized from DMF. Yield 1.92 g
Compound IXb. Yield 2.16 g (64%), mp 302 C.
1H NMR spectrum (DMSO-d6), , ppm: 3.79 d (3H,
NCH3), 6.58 8.31 m (8H, Harom), 13.40 d (1H, NH).
Found, %: C 64.10; H 5.31; N 16.63; S 10.11.
C18H18N4OS. Calculated, %: C 63.91; H 5.33;
N 16.57; S 9.47.
1
(65%), colorless crystals, mp 217 C. H NMR spec-
trum (DMSO-d6 CCl4), , ppm: 6.51 br.s (2H, NH2),
6.55 7.82 m (8H, Harom), 9.10 br.s (2H, NHCNH2),
11.82 br.s (1H, NHCNH2). Found, %: C 60.85;
H 4.56; N 23.52. C15H13N5O2. Calculated, %:
C 61.02; H 4.41; N 23.73.
2-(4,6-Dimethylpyrimidin-2-ylamino)-4-hy-
droxyquinazoline (XIII). a. A mixture of 2.31 g of
compound X and 1.63 g of isatoic anhydride (I) in
15 ml of DMF was kept for 0.5 h at room temperature.
The precipitate was filtered off and recrystallized from
dioxane. Yield 1.60 g (60%), colorless crystals,
N-Anthraniloyl-N -(2-benzothiazolyl)guanidine
(VIb). A mixture of 1.92 g of compound Vb and
1.63 g of isatoic anhydride (I) in 10 ml of DMF was
kept for 48 h at room temperature. The precipitate was
filtered off and recrystallized from DMF. Yield 1.93 g
1
mp 239 C. H NMR spectrum (DMSO-d6 CCl4), ,
ppm: 2.39 s (6H, CH3), 6.76 s (1H, 5-H, pyrimidine),
7.25 8.07 m (4H, Harom), 10.55 br.s (1H, NH),
13.27 br.s (1H, OH). Found, %: C 62.83; H 5.02;
N 26.02. C14H13N5O. Calculated, %: C 62.92; H 4.87;
N 26.22.
1
(62%), colorless crystals, mp 268 C. H NMR spec-
trum (DMSO-d6), , ppm: 6.51 br.s (2H, NH2), 6.55
7.82 m (8H, Harom), 9.10 br.s (2H, NHCNH2),
11.82 br.s (1H, NHCNH2). Found, %: C 58.02;
H 4.31; N 22.63; S 9.95. C15H13N5OS. Calculated, %:
C 57.88; H 4.18; N 22.51; S 10.29.
b. Compound XII, 1.51 g, was dissolved in 20 ml
of isopropyl alcohol, and 1.48 g of cyanamide XI and
0.92 ml of concentrated hydrochloric acid were added.
The mixture was heated for 2 h under reflux and was
then treated with a solution of 0.56 g of potassium
hydroxide in 200 ml of water. The precipitate was
filtered off and recrystallized from dioxane. Yield
2-(1,3-Benzoxazol-2-ylamino)-4-hydroxyquina-
zoline (VIIa). A mixture of 1.76 g of compound Va
and 1.63 g of isatoic anhydride (I) in 15 ml of DMF
was heated for 15 h under reflux. The mixture was
cooled, and the precipitate was filtered off and recrys-
tallized from DMF. Yield 1.61 g (58%), colorless
crystals melting above 330 C. 1H NMR spectrum
1
1.79 g (67%), colorless crystals, mp 238 C. H NMR
spectrum (DMSO-d6 CCl4), , ppm: 2.41 s (6H,
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 73 No. 7 2003