Sep-Oct 2006
Paal Knorr Reaction for Novel Pyrrolo[2,3-d]pyrimidines
1235
1
1298.90 (C=S) cm-1; H nmr (300 MHz, deuteriochloroform): ꢀ
1,3-Bis(4-chlorophenyl)-6-phenyl-7-(m-tolyl)-2-thioxo-1,2,3,7-
tetrahydropyrrolo[2,3-d]pyrimidin-4-one (5l).
6.46 (1H, s, C5-H), 7.32-7.54 (14 H, m, arom).
Anal. Calcd. for C24H15N3O4S: C, 65.30; H, 3.40; N 9.52.
Found: C, 65.19; H, 3.32; N, 9.64.
This compound has the following spectral properties: mp 260-
262°; ir: 1647.24 (C=C-C=O), 1583.02 (C=C arom), 1274.43
(C=S) cm-1; 1H nmr (300 MHz, deuteriochloroform): ꢀ 2.35 (3H,
s, CH3), 6.47 (1H, s, C5-H), 7.34-7.69 (17 H, m, arom),.
Anal. Calcd. for C31H21N3OSCl2: C, 67.14; H, 3.79; N, 7.58.
Found: C, 67.21; H, 3.83; N, 7.64.
1,3-Di(furan-2-yl)-6-phenyl-7-(m-tolyl)-2-thioxo-1,2,3,7-tetra-
hydropyrrolo[2,3-d]pyrimidin-4-one (5f).
This compound has the following spectral properties: mp
200-202°, IR: ꢀ (cm-1) 1651.09 (C=C-C=O), 1611.83 (C=C
arom), 1274.31 (C=S) cm-1; 1H nmr (300 MHz, deuterio-
chloroform): ꢀ 2.38 (3H, s, CH3), 6.46 (1H, s, C5-H), 7.28-
7.59 (15 H, m, arom).
Acknowledgement.
One of the authors Kavita Singhal acknowledges the financial
assistance by the Council of Scientific and Industrial Research
(CSIR), New Delhi.
Anal. Calcd. for C27H19N3O3S: C, 69.67; H, 4.08; N, 9.03.
Found: C, 69.74; H, 4.20; N, 9.11.
1,3-Di(m-tolyl)-6,7-diphenyl-2-thioxo-1,2,3,7-tetrahydropyrrolo-
[2,3-d]pyrimidin-4-one (5g).
REFERENCES AND NOTES
This compound has the following spectral properties: mp 216-
218°; ir: 1664.21 (C=C-C=O), 1600.61 (C=C arom), 1280.05
[1a] W. Xie, Y. Jin and P. G. Wang, Chemtech., 29, 23 (1997); [b]
M. Kidwai and R. Venkataramanan, Bull. Chem. Soc. Jpn., 76, 203
(2003); [c] H. A. Walker, S. Wilson, E. C. Atkins, H. E. Garrett and A.
R. Richardson, J. Pharmacol. Exp. Therm., 101, 368 (1951); [d] G.E.
Hardtmann and F.G. Kathawala, U.S. Patent 4,053,600, 1977; Chem.
Abstr., 88, 22970 (1978).
1
(C=S) cm-1; H nmr (300 MHz, deuteriochloroform): ꢀ 2.41(6H, s,
CH3), 6.41 (1H, s, C5-H), 7.20-7.64 (18 H, m, arom).
Anal. Calcd. for C30H25N3OS: C, 75.78; H, 5.26; N, 8.84.
Found: C, 75.87; H, 5.33; N, 8.75.
[2a] R. J. Anderson, D. J. Faulkner, H. Cun-Heng, G. D. Van
Duyne and J. Clardy, J. Am. Chem. Soc., 107, 5492 (1985); [b] A. Rudi,
I. Goldberg, Z. Stein, F. Frolow, Y. Benayahu, M. Schleyer and Y.
Kashman, J. Org. Chem., 59, 999 (1994).
[3a] T. Miwa, T. Hitaka and H. Nomura, J. Med. Chem., 34, 555
(1991); [b] H. Akimoto, T. Hitaka, T. Miwa, K. Yukishige, T. Kusangi
and K. Ootsu, Proc. Am. Assoc. Cancer Res., 32, 327 (1991).
[4] J. M. Prober, G. L. Trainor, R. J. Dam, F. W. Hobbs, C. W.
Robertson, R. J. Zagursky and A. J. Cocuzza, Science, 238, 336 (1987).
[5] A. Gangjee, F. Mavandadi, S. F. Queener and J. J. Mc Guire,
J. Med. Chem., 38, 2158 (1995).
1,3-Di(m-tolyl)-7-(furan-2-yl)-6-phenyl-2-thioxo-1,2,3,7-tetra-
hydropyrrolo[2,3-d]pyrimidin-4-one (5h).
This compound has the following spectral properties: mp 192-
194°; ir: 1650.84 (C=C-C=O), 1599.27 (C=C arom), 1268.65
(C=S) cm-1; 1H nmr (300 MHz, deuteriochloroform) ꢀ: 2.48 (6H,
s, CH3), 6.52 (1H, s, C5-H), 7.26-7.64 (16 H, m, arom).
Anal. Calcd. for C28H23N3O2S: C, 72.25; H, 4.94; N, 9.03.
Found: C, 72.28; H, 4.99; N, 9.11.
[6a] E. C. Taylor, D. Kuhnt, C. Shih, S. M. Rinzel, G. B. Grindey,
J. Barredo, M. Jannatipour and R. Moran, J. Med. Chem., 35, 4450
(1992); [b] C. Shih and L. S. Gossett, Heterocycles, 35, 825 (1993).
[7] T. A. Bluemenkopf, M. E. Flanagan, M. F. Brown and P. S.
Changelian, PCT Int. Appl. WO 99 65,909; Chem. Abstr., 132(5),
49976f (2000).
[8] C. O. Kappe, Angew. Chem. Int. Ed., 43, 6250 (2004).
[9a] M. Kidwai, S. Saxena, M. R. Khalilur and S. S. Thukral,
Biomed. & Chem. Lett., 15 (19), 4295 (2005); [b] B. S. Chhikara, V.
Tandon and A. K. Mishra, Hetero. Commun., 10, 441 (2004).
[10] M. Kidwai, K. Singhal and R. Thakur, Lett. Org. Chem., 2,
419 (2005).
[11] A. Loupy, A. Petit, J. Hamelin, B.F. Taxier, P. Jacqualt and
D. Matha, Synthesis, 1213 (1998).
[12] M. Liagre, A. Loupy, A. Oussaid, A. Petit and J. Cleophax, Scaling
up of some typical organic reactions under focused microwaves, presented at
the International Conference on Microwave Chemistry; Prague, Czech
Republic, September 6-11, 1998.
1,3,7-Tri(m-tolyl)-6-phenyl-2-thioxo-1,2,3,7-tetrahydropyrrolo-
[2,3-d]pyrimidin-4-one (5i).
This compound has the following spectral properties: mp 212-
215°; ir: 1649.27 (C=C-C=O), 1608.84 (C=C arom), 1271.05
(C=S) cm-1; 1H nmr (300 MHz, deuteriochloroform): ꢀ 2.35 (9H,
s, CH3), 6.39 (1H, s, C5-H), 7.28-7.59 (17 H, m, arom)
Anal. Calcd. for C31H27N3OS: C, 76.07; H, 5.52; N, 8.58.
Found: C, 76.16; H, 5.61; N, 8.64.
1,3-Bis(4-chlorophenyl)-6,7-diphenyl-2-thioxo-1,2,3,7-tetrahydro-
pyrrolo[2,3-d]pyrimidin-4-one (5j).
This compound has the following spectral properties: mp 188-
190°; ir: 1664.91 (C=C-C=O), 1605.62 (C=C arom), 1268.05
(C=S) cm-1; 1H nmr (300 MHz, deuteriochloroform): ꢀ 6.46 (1H,
s, C5-H), 7.31-7.65 (18 H, m, arom).
Anal. Calcd. for C30H19N3OSCl2: C, 66.66; H, 3.51; N, 7.77.
Found: C, 66.70; H, 3.44; N, 7.67.
[13] M. P. Sammes, P. N. Maini and A. R. Katritzky, J. Chem.
Soc. Chem. Commun., 354 (1984).
[14] E. C. Taylor and B. Liu, Tetrahedron Lett., 40, 4027 (1999).
[15] H. Ogura, M. Sakaguchi and K. Takeda, Chem. Pharma.
Bull., 20(2), 404 (1972).
1,3-Bis(4-chlorophenyl)-7-(furan-2-yl)-6-phenyl-2-thioxo-1,2,3,7-
tetrahydro-pyrrolo[2,3-d]pyrimidin-4-one (5k).
[16] E. D. Edstrom and Y. Wei, J. Org. Chem., 60, 5069 (1995).
[17] X. Chen, S. M. Siddiqi and S. W. Schneller, Tetrahedron
Lett., 33, 2249 (1992).
[18] Aluminium Oxide Basic, Brockmann I (Aldrich Chem. Co.,
Cat. No. 19, 944-3), ~150 mesh, 58 Å, surface area 155 m2/gm.
[19] Aluminium Oxide Acidic, Brokmann I (~ 150 mesh, 58 Å,
CAMAG 506-C-1, surface area 155 m2/gm).
This compound has the following spectral properties: mp
236-238°; ir: 1652.68 (C=C-C=O), 1599.36 (C=C arom),
1
1290.19 (C=S) cm-1; H nmr (300 MHz, deuteriochloroform): ꢀ
6.41 (1H, s, C5-H), 7.29-7.60 (16 H, m, arom).
Anal. Calcd. for C28H17N3O2SCl2: C, 63.39; H, 3.20; N, 7.92.
Found: C, 63.41; H, 3.28; N, 7.87.