1256
M. Kidwai and K. Singhal
Vol 44
Hz, 1H, thienyl), 8.40 (d, J = 4.5 Hz, 1H, thienyl), 10.31 (s, 1H,
NH), 11.27 (s, 1H, NH). Anal. Calcd. for C9H7N3O3S: C, 45.56;
H, 2.95; N, 17.72; Found: C, 45.64; H, 2.91; N, 17.76.
7-Hydrazino-5-phenylpyrimido[4,5-d]pyrimidine-2,4(1H,
3H)-dione (7a). mp160-162°; ir: 3462, 3391, 3223, 1732,
1669, 1598 cm-1; 1H nmr: ꢀ 7.27 (d, J = 8.0 Hz, 2H, Ar-H), 7.63-
7.66 (t, 3H, Ar-H), 7.98 (s, 1H, NH), 10.31 (s, 1H, NH), 11.28
(s, 1H, NH). Anal. Calcd. for C12H10N6O2: C, 44.44; H, 3.70; N,
31.11; Found: C, 44.37; H, 3.62; N, 31.19.
7-Hydrazino-5-(4-methoxyphenyl)pyrimido[4,5-d]pyrim-
idine-2,4(1H,3H)-dione (7b). mp 154-156°; ir: 3460, 3384,
3223, 1738, 1699, 1595 cm-1; 1H nmr: ꢀ 3.8 (s, 3H, OCH3), 7.24-
7.36 (m, 4H, Ar-H), 7.96 (s, 1H, NH), 10.29 (s, 1H, NH), 11.28
(s, 1H, NH). Anal. Calcd. for C13H12N6O3: C, 52.00; H, 4.00; N,
28.00; Found: C, 51.94; H, 4.06; N, 28.13.
3-(2-Chloroquinolinyl)-2-phenyl-3,3a-dihydro-2H-pyra-
zolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (3d). mp 220-224°;
ir: 3315, 3208, 1726, 1668, 1595 cm-1; 1H nmr: ꢀ 3.21 (d, J = 3.3
Hz, 1H, C3a-H), 4.78 (d, J = 3.3 Hz, 1H, C3-H), 7.43-7.75 (m,
10H, Ar-H), 10.29 (s, 1H, NH), 11.33 (s, 1H, NH). Anal. Calcd.
for C20H14N5O2Cl: C, 61.30; H, 3.57; N, 17.87; Found: C, 61.21;
H, 3.63; N, 17.89.
3-(4-Chlorophenyl)-2-phenyl-3,3a-dihydro-2H-pyrazolo-
[3,4-d]pyrimidine-4,6-(5H,7H)-dione (3e). mp 182-184°; ir:
3213, 1730, 1672, 1597 cm-1; 1H nmr: ꢀ 3.18 (d, J = 3.2 Hz, 1H,
C3a-H), 4.80 (d, J = 3.2 Hz, 1H, C3-H), 7.47-7.60 (m, 9H, Ar-H),
10.31 (s, 1H, NH), 11.27 (s, 1H, NH). Anal. Calcd. for
C17H13N4O2Cl: C, 59.91; H, 3.81; N, 16.44; Found: C, 59.87; H,
3.86; N, 16.35.
3-(2-Thienyl)-2-phenyl-3,3a-dihydro-2H-pyrazolo[3,4-d]-
pyrimidine-4,6(5H,7H)-dione (3f). mp 194°(d); ir: 3306, 3210,
5-(1,3-Benzodioxol-5yl)-7-hydrazinopyrimido[4,5-d]pyrim-
idine-2,4(1H,3H)-dione (7c). mp 180-182°; ir: 3452, 3394,
1
1733, 1666, 1597 cm-1; H nmr: ꢀ 3.21 (d, J = 3.1 Hz, 1H, C3a-
1
3220, 1740, 1701, 1599 cm-1; H nmr: ꢀ 5.86 (s, 2H, OCH2O),
H), 4.79 (d, J = 3.1 Hz, 1H, C3-H), 7.48-7.53 (m, 6H, Ar-H +
thienyl), 8.11 (d, J = 3.0 Hz, 1H, thienyl-H), 8.36 (d, J = 4.6 Hz,
1H, thienyl-H) 10.31 (s, 1H, NH), 11.27 (s, 1H, NH). Anal.
Calcd. for C15H12N4O2S: C, 57.69; H, 3.84; N, 17.94; Found: C,
57.77; H, 3.81; N, 17.86.
6.68 (d, 1H, J = 8.0, Ar-H), 6.86 (d, 1H, J = 8.0, Ar-H), 7.04 (s,
1H, Ar-H), 7.87 (s, 1H, NH), 10.30 (s, 1H, NH), 11.31 (s, 1H,
NH). Anal. Calcd. for C13H10N6O4: C, 49.68; H, 3.18; N, 26.75;
Found: C, 49.52; H, 3.21; N, 26.78.
3-Phenyl-3,3a-dihydroisoxazolo[3,4-d]pyrimidine-4,6(5H,
7H)-dione (5a). mp 112-114°; ir: 3410, 3394, 3230, 1698, 1599,
1260 cm-1; 1H nmr: ꢀ 3.21 (d, J = 3.2 Hz, 1H, C3a-H), 4.79 (d, J
= 3.2 Hz, 1H, C3-H), 7.24-7.26 (d, J = 8.0 Hz, 2H, Ar-H), 7.63-
7.66 (m, 3H, Ar-H), 10.29 (s, 1H, NH), 11.27 (s, 1H, NH). Anal.
Calcd. for C11H9N3O3: C, 57.14; H, 3.89; N, 18.18; Found: C,
57.22; H, 3.92; N, 18.10.
5-(2-Chloroquinolinyl)-7-hydrazinopyrimido[4,5-d]pyrim-
idine-2,4(1H,3H)-dione (7d). mp 176-178°; ir: 3459, 3391,
1
3228, 1727, 1698, 1595 cm-1; H nmr: ꢀ 7.76-7.82 (m, 5H, Ar-
H), 7.89 (s, 1H, NH), 10.28 (s, 1H, NH), 11.30 (s, 1H, NH).
Anal. Calcd. for C15H10N7O2Cl: C, 50.63; H, 2.81; N, 27.56;
Found: C, 50.56; H, 2.79; N, 27.60.
5-(4-Chlorophenyl)-7-hydrazinopyrimido[4,5-d]pyrim-
idine-2,4(1H,3H)-dione (7e). mp 180-182°; ir: 3462, 3390,
3212, 1730, 1682, 1598 cm-1; 1H nmr: ꢀ 7.47 (d, J = 8.0 Hz, 2H,
Ar-H), 7.59-7.61 (d, J = 8.0 Hz, 2H, Ar-H), 7.96 (s, 1H, NH),
10.31 (s, 1H, NH), 11.28 (s, 1H, NH). Anal. Calcd. for
C12H9N6O2Cl: C, 47.29; H, 2.95; N, 27.58; Found: C, 47.33; H,
2.98; N, 27.51.
3-(4-Methoxyphenyl)-3,3a-dihydroisoxazolo[3,4-d]pyrim-
idine-4,6(5H,7H)-dione (5b). mp 98-100°; ir: 3416, 3390, 3216,
1
1698, 1595, 1264 cm-1; H nmr: ꢀ 3.19 (d, J = 3.2 Hz, 1H, C3a-
H), 3.81 (s, 3H, OCH3), 4.80 (d, J = 3.2 Hz, 1H, C3-H), 7.24-
7.37 (m, 4H, Ar-H), 10.29 (s, 1H, NH), 11.31 (s, 1H, NH). Anal.
Calcd. for C12H11N3O4: C, 55.17; H, 4.21; N, 16.09; Found: C,
55.24; H, 4.16; N, 16.01.
7-Hydrazino-5-(2-thienyl)pyrimido[4,5-d]pyrimidine-
2,4(1H,3H)-dione (7f). mp 224-226°; ir: 3460, 3384, 3218,
3-(1,3-Benzodioxol-5-yl)-3,3a-hydroisoxazolo[3,4-d]pyrim-
idine-4,6(5H,7H)-dione (5c). mp 88-90°; ir: 3420, 3390, 3223,
1
1738, 1699, 1590 cm-1; H nmr: ꢀ 7.47-7.49 (t, 1H, thienyl),
1
1700, 1605, 1258 cm-1; H nmr: ꢀ 3.18 (d, J = 3.1 Hz, 1H, C3a-
7.92 (s, 1H, NH), 8.01 (d, J = 3.0 Hz, 1H, thienyl), 8.36 (d, J =
4.8 Hz, 1H, thienyl) 10.31 (s, 1H, NH), 11.27 (s, 1H, NH). Anal.
Calcd. for C10H8N6O2S: C, 43.47; H, 2.89; N, 30.43; Found: C,
43.39; H, 2.82; N, 30.45.
H), 4.79 (d, J = 3.1 Hz, 1H, C3-H), 5.8 (s, 2H, OCH2O), 6.70 (d,
1H, J = 8.0, Ar-H), 6.87 (d, 1H, J = 8.0, Ar-H), 7.02 (s, 1H, Ar-
H), 10.28 (s, 1H, NH), 11.31 (s, 1H, NH). Anal. Calcd. for
C12H9N3O5: C, 52.36; H, 3.27; N 15.27; Found: C, 52.28; H,
3.23; N, 15.35.
3-(2-Chloroquinolinyl)-3,3a-dihydroisoxazolo[3,4-d]pyrim-
idine-4,6(5H,7H)-dione (5d). mp 166-168°; ir: 3420, 3391,
3220, 1699, 1595, 1258 cm-1; 1H nmr: ꢀ 3.21 (d, J = 3.2 Hz, 1H,
C3a-H), 4.80 (d, J = 3.2 Hz, 1H, C3-H), 7.68-7.74 (m, 5H, Ar-H),
10.27 (s, 1H, NH), 11.29 (s, 1H, NH). Anal. Calcd. for
C14H9N4O3Cl: C, 53.08; H, 2.84; N, 17.69; Found: C, 53.14; H,
2.76; N, 17.54.
Acknowledgement. Financial assistance provided by the
Council of Scientific and Industrial Research (CSIR), New Delhi
to authors is highly acknowledged.
REFERENCES AND NOTES
[1] Anastas, P.; Williamson, T. Green Chemistry Frontiers in
Benign Chemical synthesis and procedure: Oxford Science Publications
1998.
3-(4-Chlorophenyl)-3,3a-dihydroisoxazolo[3,4-d]pyrimidine-
4,6(5H,7H)-dione (5e). mp 104-106°; ir: 3418, 3394, 3223,
[2] (a) Kidwai, M.; Venketaramanan, R.; Dave, B. Green Chem.
2001, 3, 278. (b) Clifford, A. A.; Rayer, C. M. Tetrahedron Lett. 2001,
42, 323. (c) Darr, J. A.; Poliakoff, M. Chem. Rev. 1999, 99, 495.
[3] (a) Wasserscheid, P.; Welton, T. Ionic Liquid in Synthesis,
Eds. Wiley-VCh: Weinheim, Germany, 2003. (b) Chandrasekhar, S.;
Narsihmulu, Ch.; Sultana, S. S.; Reddy, N. R. Org. Lett. 2002, 4, 4399.
[4] (a) Meijer, A.; Otto, S.; Engberts, J. B. F. N. J. Org. Chem.
1998, 63, 8989. (b) Li, C. J. Chem. Rev. 1993, 93, 2023.
1
1699, 1598, 1260 cm-1; H nmr: ꢀ 3.20 (d, J = 3.3 Hz, 1H, C3a-
H), 4.81 (d, J = 3.3 Hz, 1H, C3-H), 7.45 (d, J = 8.0 Hz, 2H, Ar-
H), 7.56 (d, J = 8.0 Hz, 2H, Ar-H), 10.31 (s, 1H, NH), 11.27 (s,
1H, NH). Anal. Calcd. for C11H8N3O3Cl: C, 49.71; H, 3.01; N,
15.81; Found: C, 49.66; H, 3.08; N, 15.89.
3-(2-Thienyl)-3,3a-dihydroisoxazolo[3,4-d]pyrimidine-4,
6(5H,7H)-dione (5f). mp >300°; ir: 3402, 3390, 3220, 1698,
[5] (a) Kidwai, M.; Singhal, K.; Rastogi, S. J. Heterocycl. Chem.
2006, 43, 1231. (b) Kidwai, M.; Singhal, K.; Thakur, R. Lett. Org.
Chem. 2005, 2, 419. (c) Kidwai, M.; Sapra, P.; Bhushan, K. R.; Misra, P.
1
1600, 1262 cm-1; H nmr: ꢀ 3.1 (d, J = 3.2 Hz, 1H, C3a-H), 4.83
(d, J = 3.2 Hz, 1H, C3-H), 7.48 (t, 1H, thienyl), 8.12 (d, J = 3.0