J. Chil. Chem. Soc., 58, Nº 3 (2013)
+
HRESIMS: m/z 163.0497 for C H N O [M+H] , calculated: m/z 163.0508.
18. T. Mizuno, T. Iwai, Y. Ishino; Tetrahedron Lett. 45 (2005) 7073-7075.
19. T. Miyata, T. Mizuno, Y. Nagahama, I. Nishiguchi, T. Hirashima, N.
Sonoda,; Heteroat. Chem, 2 (1991) 473–475.
20. N. A. Lange and F. E. Sheibley. Org. Synt. 2 (1943) 79.
21. G. D. Mendenhall, P. Smith. Org. Synt. 46 (1966) 85.
22. J. Bernstein, R.E. Davis, L. Shimoni, & N.-L. Chang, Angew. Chem. Int.
Ed. Engl. 34 (1995) 1555–1573.
23. F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen & R.
Taylor. J. Chem. Soc. Perkin Trans. 2 (1987) S1-19.
24. Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.
25. G.M. Sheldrick, Acta Cryst. A64 (2008) 112-122.
8
7
2
2
Synthesis of 6-Nitroquinazoline-2,4(1H,3H)-dione. 3
On an ice bath, 2 g (12,3 mmol) of quinazoline-2,4(1H,3H)-dione 2, were
dissolved in 19 mL of sulfuric acid. Maintaining the mixture under agitation,
a solution of 0.68 mL of nitric acid (12.3 mmol) and 1.37 mL of sulfuric acid
were by dropwise added during 30 minutes and left reacting for 3 hours at 0°C.
After this time, the reaction mixture was poured into a beaker containing 70
ml cold water. Subsequently, 70 ml of solution 9.5N of NaOH was dropwise
added. The resulting precipitate was filtered at vacuum, dried and purified by
chromatographic column using petroleum-ether/ethylacetate (3/7) as eluent.
This gave 2.1 g (82% yield) of a yellow product.
Spectroscopic Data:
26. O.V. Dolomanov, L.J. Bourhis, R.J. Gildea, J.A.K. Howard, H. Puschmann.
OLEX2: A complete structure solution, refinement and analysis program.
J. Appl. Cryst. 42 (2009) 339-341.
-1
IR (cm ) 3338 (N-H), 3018 (Csp2-H), 1683 (C=O), 1533 (CAr-NO ).
2
1
H-NMR (DMSO-d6, 500 MHz) (ppm): 7.32 (1H, d, J= 9, H4), 8.45 (1H,
dd, J= 9, H3), 8.59 (1H, d, J=6.6, H1), 11.69 (1H, s, H6), 11.74 (1H, s, H8).
27. A. L. Spek, Acta Cryst. D65 (2009) 148-155.
28. R. H. Blessing, Acta Cryst. A51 (1995) 33-38.
13
C-NMR (DMSO-d6, 125.70 MHz) (ppm): 114.51 (C10), 116.64 (C4),
1
23.06 (C1), 141.84 (C2), 145.61 (C5), 149.93 (C7), 161.57 (C9).
+
HRESIMS: m/z 206.0193 for C H N O [M-H] , calculated: m/z 206.0202.
8
4
3
4
X- Ray Crystallography
Single crystal analysis data were collected on a Stoe IPDS-II two-circle
2
4
Diffractometer with MoKα radiation. Data collection: X-AREA ; cell
2
4
24
refinement X-AREA ; data reduction: X-AREA . Program used to solve
2
5
structure program(s) used to refine structure: SHELXL97 ; molecular graphics:
XP in SHELXTL-Plus & OLEX2 , software used to prepare material for
publication: SHELXL97 . Crystal dimension of C H N O , 0.37x 0.35x0.12
mm ; Mr = 207.15 Dalton; Monoclinic P21/c; a = 10.9071(8) Å; b = 6.5758(6)
Å; c = 12.4614(9) Å; α = 90°; β = 112.382(5)°; γ = 90.0°; V = 826.44(11) Å ; Z
4; m = 0.137 mm ; T = 173(2) K; absorption correction Semi-empirical from
25
26
2
5
8
5
3
4
3
3
-1
=
27 - 28
equivalents
; max. and min. transmission 0.9837 and 0.9509. 8995/1898
measured/unique reflection with I>2s(I) [R = 0.0556]; R[I>2s(I)] 0.0393, wR
int
2
-3
-3
=
0.1093; S = 1.097; 144 parameters; Drmax= 0.284 eÅ and Dr = -0.209 eÅ .
min
H1 and H2 atoms were freely refined; all H atoms were located in difference
maps and their positions and isotropic displacements parameters of 1.2 times
those of the attached atoms. Supplementary information: Crystallographic data
(excluding structure factors) for the structural analysis have been deposited in
the Cambridge Crystallographic Data Centre, CCDC 927348. These data can
be obtained free of charge from the Cambridge Crystallographic Data Centre;
Postal Address : CCDC, 12 Union Road , Cambridge CB21EZ, UK, Telephone:
(44) 01223 762910, Fax: (44) 01223 336033, e-mail: deposit@ccdc.cam.ac.uk
REFERENCES
1
.
J. Bartroli, E. Turmo, M. Alguero, E. Boncompte, M.L. Vericant, J. Conte
Ramis, M. Merlos, J.F. Gracia-Rafanell. J. Med. Chem. 48 (1998) 1869-
1
882.
2.
3.
4.
I.M.Sh. El-Sharief, Y.A. Ammar, M.A. Zahran, A.H. Ali, M.S.A. El-
Gaby, Molecules 6 (2001) 267-278.
D.M. Purohit, V.R. Bhuva, V.H. Shah, An Indian Journal 1 (2003) 233-
2
45.
K.M. Murav’eva, N.V. Arkhangel’skaya, M.N. Shchukina, T.N. Zykova,
G.N. Pershin, Khim. Farm. Zh. 5 (1971) 25-27.
5
6
7
.
.
.
S.G. Abdel-Hamid, J. Indian Chem. Soc. 74 (1997) 613-618.
A.J. Barker, Eur. Pat 635498, 1995 [Chem. Abstr. 122 (1995) 214099].
M.A. Aziza, M.K. Ibrahim, A.G. El-Helpy, Al-Azhar J. Pharm. Sci. 14
(
1994) 193-201.
N. Ergenc, S. Buyuktimkin, G. Capan, G. Baktir, S. Rollas, Pharmazie 46
1991) 290-291.
A.A. Bekhit, M.A. Khalil, Pharmazie 53 (1998) 539-544.
8
.
.
(
9
1
0. E. Hamel, C.M. Lin, J. Plowman, H.K. Wang, K.H. Lee, K.D. Paull.
Biochem. Pharmacol. 51 (1996) 53-59.
11. K. Terashima, H. Shimamura, A. Kawase, Y. Tanaka, T. Tanimura, T.
Kamisaki, Y. Ishizuka, M. Sato. Chem. Pharm. Bull. 43 (1995) 2021-2023.
2. A. Gursoy, N. Karali, Farmaco 50 (1995) 857-866.
3. D.J. Baek, Y.K. Park, H.I. Heo, M.H. Lee, Z.Y. Yang, M.H. Chio, Bioorg.
Med. Chem. Lett. 8 (1998) 3287-3290.
1
1
1
4. R.J. Grif fi n, S. Srinivasan, K. Bowman, A.H. Calvert, N.J. Curtin, D.R.
Neweli, L.C. Pemberton, B.T. Golding, J. Med. Chem. 41 (1998) 5247-
5
256.
1
1
5. B. Sumegi, K. Hideg, T. Kalai. US Pat. Appl. 20070042935, 2007.
6. M. Uehara, T. Shimizu, S. Fujioka, M. Kimura, K. Tsubata, A. Seo. Pestic.
Sci. 55 (1999) 359-362.
1
7. G.P. Ouyang, P.Q. Zhang, G.F. Xu, B.A. Song, S. Yang, L.H. Jin, W. Xue,
D.Y. Hu, P. Lu, Z. Chen. Molecules 11 (2006) 383-392.
1
819