S. Ahadi et al. / Tetrahedron 68 (2012) 2906e2916
2915
requires C, 57.86; H, 4.01; N, 14.67%]; nmax (KBr) 3433, 3343, 2958,
1677, 1594 cmꢁ1
dH (300 MHz, DMSO-d6) 3.16 (6H, s, CH3),
125.9, 131.6, 134.3, 134.4, 136.1, 140.5, 146.1, 153.0, 173.0, 180.2,
184.6, 201.1.
;
7.19e7.22 (2H, m, H-Ar), 7.32e7.35 (2H, m, H-Ar), 7.59e7.83 (4H, m,
H-Ar), 8.39 (2H, s, NH2), 11.44 (1H, br s, NH), 12.41e12.44 (1H, br s,
OH); dC (75 MHz, DMSO-d6) 28.7, 76.9,11.7,113.9,123.4,125.0,125.9,
130.1, 131.6, 134.3, 150.4, 151.6, 171.3, 172.6, 180.1, 184.6.
4.2.42. 5-Hydroxy-5-(2-oxoindolin-3-yl)pyrimidine-2,4,6(1H,3H,5H)-
trione (15). (253.05 g, 91%) as dark red powder, mp 232e234 ꢀC.
[Found: C, 52.26; H, 3.24; N, 15.21. C12H9N3O5 requires C, 52.37; H,
3.30; N, 15.27%]; nmax (KBr) 3336, 3295, 3217, 1730, 1694 cmꢁ1
; dH
4.2.36. 2-Amino-1H-benzo[d]imidazol-3-ium 3-hydroxy-1-(5-
hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)-2,5,6-trioxocyclohex-
3-en-1-ide (10). (394.02 g, 99%) as light pink powder, mp
201e203 ꢀC. [Found: C, 49.05; H, 3.08; N, 16.73. C17H13N5O8 re-
quires C, 49.16; H, 3.16; N, 16.86%]; nmax (KBr) 3391, 3246, 2983,
(300 MHz, DMSO-d6) 4.20 (1H, s, CH), 6.75e7.39 (5H, m, H-Ar and
NH), 10.54 (1H, s, NH), 11.33 (1H, s, NH), 11.54 (1H, s, OH); dC
(75 MHz, DMSO-d6) 51.2, 73.9, 109.6, 121.7, 126.3, 126.5, 128.3, 143.1,
150.2, 169.0, 171.1, 175.1.
1714, 1675 cmꢁ1
; dH (300 MHz, DMSO-d6) 5.52 (1H, s, CH),
Acknowledgements
6.86e7.56 (4H, m, H-Ar), 7.96 (3H, s, NH2 and OH), 10.61 (1H, s, NH),
10.43e11.08 (2H, br s, 2NH); dC (75 MHz, DMSO-d6) 75.8, 75.9,
102.5, 107.5, 107.7, 111.8, 122.7, 131.8, 150.8, 150.9, 151.9, 172.4, 172.6,
175.6, 178.0.
We gratefully acknowledge financial support from the Research
Council of Shahid Beheshti, University.
References and notes
4.2.37. 2-Aminopyridinium 3-(2-hydroxy-1,3-dioxo-2,3-dihydro-1H-
inden-2-yl)-2,4-dioxochroman-3-ide (12a). (332.88 g, 80%) as yel-
low powder, mp 170e172 ꢀC. [Found: C, 66.46; H, 3.82; N, 6.79.
C23H16N2O6 requires C, 66.34; H, 3.87; N, 6.73%]; nmax (KBr) 3387,
1. (a) Orru, R. V. A.; De Greef, M. Synthesis 2003, 1471e1499; (b) Schreiber, S. L.
Science 2000, 287, 1964e1969; (c) Zhu, J.; Bienayme, H. Multicomponent Re-
ꢀ
actions; Wiley-VCH: Weinheim, Germany, 2005; (d) Domling, A. Chem. Rev.
2006, 106, 17e89; (e) Weber, L. Curr. Med. Chem. 2002, 9, 2085e2093; (f) Bi-
enayme, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem.dEur. J. 2000, 6,
3321e3329; (g) Abboub, F.; Amari, M.; Kolli, B. J. Soc. Alger. Chim. 2001, 11,
223e230; (h) Do_mling, A. Curr. Opin. Chem. Biol. 2002, 6, 306e313.
3090, 1738, 1707, 1637 cmꢁ1
; dH (300 MHz, DMSO-d6) 3.55 (br s, NH
and OH, overlap with solvent), 6.77e6.81 (1H, m, H-Ar), 6.87e6.89
(1H, m, H-Ar), 7.15e7.22 (2H, m, H-Ar), 7.43e7.92 (10H, m, H-Ar and
NH2); dC (75 MHz, DMSO-d6) 78.7, 92.8, 112.5, 113.1, 116.3, 123.1,
123.4, 124.1, 131.2, 136.1, 137.9, 140.5, 143.6, 153.9, 155.0, 163.9, 175.7.
ꢀ
2. (a) Lieby-Muller, F.; Constantieux, T.; Jean Rodriguez, J. J. Am. Chem. Soc. 2005,
127, 17176e17177; (b) Rivera, D. G.; Wessjohann, L. A. J. Am. Chem. Soc. 2006,
128, 7122e7123; (c) Chebanov, V. A.; Saraev, V. E.; Desenko, S. M.; Chernenko,
V. N.; Knyazeva, I. V.; Groth, U.; Glasnov, T. N.; Kappe, C. O. J. Org. Chem. 2008,
73, 5110e5118; (d) Groenendaal, B.; Vugts, D. J.; Schmitz, R. F.; de Kanter, F. J. J.;
Ruijter, E.; Groen, M. B.; Orru, R. V. A. J. Org. Chem. 2008, 73, 719e722; (e)
Abbiati, G.; Arcadi, A.; Canevari, V.; Capezzuto, L.; Rossi, E. J. Org. Chem. 2005,
70, 6454e6460; (f) Sunderhaus, J. D.; Dockendorff, C.; Martin, S. F. Org. Lett.
2007, 9, 4223e4226; (g) Nair, V.; Menon, R. S.; Beneesh, P. B.; Sreekumar, V.;
Bindu, S. Org. Lett. 2004, 6, 767e769; (h) Zhang, M.; Jiang, H.; Liu, H.; Zhu, Q.
Org. Lett. 2007, 9, 4111e4113; (i) Heravi, M. M.; Baghernejad, B.; Oskooie, H. A.;
Hekmatshoar, R. Tetrahedron Lett. 2008, 49, 6101e6103; (j) Willy, B.; Mu_ller, T. J.
J. Eur. J. Org. Chem. 2008, 4157e4168; (k) Umkehrer, M.; Kolb, J.; Burdack, C.;
Hiller, W. Synlett 2005, 79e82.
4.2.38. 2-Aminopyridinium 3-(2-hydroxy-1,3-dioxo-2,3-dihydro-1H-
inden-2-yl)-6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ide
(12b). (311.68 g, 82%) as yellow powder, mp 226e227 ꢀC. [Found:
C, C, 63.28; H, 4.33; N, 7.28. C20H16N2O6 requires C, C, 63.16; H, 4.24;
N, 7.37%]; nmax (KBr) 3336, 3167, 3084, 2827, 1709, 1660 cmꢁ1
; dH
(300 MHz, DMSO-d6) 2.29 (3H, s, CH3), 4.97 (1H, s, CH), 6.11 (br s,
NH and OH and NH2, overlap with solvent), 6.48 (2H, m, H-Ar),
7.39e7.94 (6H, m, H-Ar); dC (75 MHz, DMSO-d6) 20.4, 76.7, 86.8,
91.7, 109.0, 112.2, 123.7, 136.6, 138.2, 140.4, 146.6, 159.5, 159.8, 159.9,
163.1, 166.3.
3. Goodman and Gilman’s. In The Pharmacological Basis of Therapeutics, 9th ed.;
McGraw-Hill: New York, 1996; p 471.
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787e791.
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Panwar, H.; Agarwal, A.; Kumar, A. Indian J. Pharm. Sci. 2005, 67, 194e199.
6. Osman, A. N.; Kandeel, M. M.; Ahmed, M. Indian J. Chem. 1996, 35B, 1073e1078.
7. Archana, S.; Rani, P.; Bajaj, K.; Chandora, R.; Srivastava, V. K.; Kumar, A. Arzneim.
Forsch., Drug. Res. 2003, 53, 301e306.
8. Sarma, G. V. S. R.; Rao, J. V.; Suresh, B. Indian J. Pharm. Sci. 1999, 61, 105e109.
9. Gupta, K. P.; Gupta, R. C.; Bhargava, K. P.; Ali, B. Eur. J. Med. Chem. 1982, 17,
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10. Padmavati, V.; Reddy, B. J. M.; Venketa Subbaiah, D. R. C.; Padmaja, A. Indian J.
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4.2.39. 2-Aminopyridinium 2-(2-hydroxy-1,3-dioxo-2,3-dihydro-1H-
inden-2-yl)-1,3,4-trioxo-1,2,3,4-tetrahydronaphthalen-2-ide
(12c). (393.82 g, 92%) as orange powder, mp 203e205 ꢀC. [Found:
C, 67.21; H, 3.69; N, 6.46. C24H16N2O6 requires C, 67.29; H, 3.76; N,
6.54%]; nmax (KBr) 3430, 3341, 3216, 2666, 1714, 1672 cmꢁ1
; dH
(300 MHz, DMSO-d6) 3.67 (br s, NH and OH, overlap with solvent),
6.81e7.57 (3H, m, H-Ar), 7.66 (2H, s, NH2), 7.80e7.94 (9H, m, H-Ar);
dC (75 MHz, DMSO-d6) 79.4, 112.5, 112.8, 113.5, 123.5, 125.0, 131.6,
134.3, 136.1, 137.1, 140.5, 144.1, 154.6, 172.9, 180.2, 184.5, 200.9.
13. Olin. B.R., Ed. Central Nervous System Drugs, Sedatives and Hypnotics, Barbi-
turates. In Facts and Comparisons Drug Information, Facts and Comparisons, St.
Louis, MO, 1993, 1398e1413.
4.2.40. 2-Amino-5-methylpyridinium 3-(2-hydroxy-1,3-dioxo-2,3-
dihydro-1H-inden-2-yl)-2,4-dioxochroman-3-ide (12d). (400.74 g,
93%) as yellow powder, mp 190e191 ꢀC. [Found: C, 66.87; H, 4.17; N,
6.61. C24H18N2O6 requires C, 66.97; H, 4.22; N, 6.51%]; nmax (KBr)
14. (a) Naguib, F. N. M.; Levesque, D. L.; Wang, E.-C.; Panzica, R. P.; El kouni, M. H.
Biochem. Pharmacol. 1993, 30, 1273e1283; (b) Levesque, D. L.; Wang, E.-C.; Wei,
D.-C.; Et Kouni, M. H.; Naguib, F. N. M. J. Heterocycl Chem. 1993, 30, 1399e1404;
(c) Oliva, A.; De Cillis, G.; Grams, F.; Livi, V.; Zimmerman, G.; Menta, E.; Krell, H.
W. U.S. Patent 6,335,332, B1, 2002; (d) Ashkinazi, R. I. Int. Patent, WO 99/25699,
1999; (e) Neumann, D. M.; Jursic, B. S.; Morgan, L.-R. Abstracts of Papers, 225th
ACS National Meeting, New Orleans, LA, United States, 2003, 23e27.
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Skiles, J. W.; Gonnella, N. C; Jeng, A. Y. Curr. Med. Chem. 2004, 11, 2911e2977.
16. Zhao, T.; Sun, G. J. Appl. Microb. 2008, 104, 824e830.
3412, 3305, 1751, 1714, 1675, 1637 cmꢁ1
; dH (300 MHz, DMSO-d6)
2.12 (3H, s, CH3), 3.67 (br s, NH and OH, overlap with solvent),
6.84e7.95 (11H, m, H-Ar and NH2); dC (75 MHz, DMSO-d6) 16.8,
78.7, 92.8, 113.2, 116.3, 121.9, 122.0, 123.1, 124.1, 131.3, 134.5, 136.1,
140.5, 146.1, 153.0, 153.9, 164.0, 175.7.
17. Zhao, T.; Sun, G. J. Surf. Deterg. 2006, 9, 325e330.
18. Zhao, T.; Sun, G. J. Appl. Polymer Sci. 2007, 103, 482e486.
19. Calas, M.; Outtara, M.; Piquet, G.; Ziora, Z.; Bordat, Y.; Ancelin, M. L.; Escale, R.;
4.2.41. 2-Amino-5-methylpyridinium 2-(2-hydroxy-1,3-dioxo-2,3-
dihydro-1H-inden-2-yl)-1,3,4-trioxo-1,2,3,4-tetrahydronaphthalen-
2-ide (12e). (402.33 g, 91%) as dark red powder, mp 232e233 ꢀC.
[Found: C, 67.95; H, 4.17; N, 6.24. C25H18N2O6 requires C, 67.87; H,
Vial, H. J. Med. Chem. 2007, 50, 6307e6315.
20. Wang, Qi-F.; Hui, L.; Hou, H.; Yan, Ch-G. J. Comb. Chem. 2010, 12, 260e265.
21. Han, Y.; Chen, J.; Hui, L.; Yan, Ch-G. Tetrahedron 2010, 66, 7743e7748.
22. Braga, D.; Cadoni, M.; Grepioni, F.; Maini, L.; Streek, J. New J. Chem. 2007, 31,
1935e1940.
23. Bertolasi, V.; Gilli, P.; Ferretti, V.; Gilli, G. New J. Chem. 2001, 25, 408e415.
24. Moafi, L.; Ahadi, S.; Khavasi, H. R.; Bazgir, A. Synthesis 2011, 1399e1402.
25. Moafi, L.; Ahadi, S.; Bazgir, A. Tetrahedron Lett. 2010, 51, 6270e6274.
4.10; N, 6.33%]; nmax (KBr) 3430, 3341, 3216, 2666, 1714, 1672 cmꢁ1
;
dH (300 MHz, DMSO-d6) 2.12 (3H, s, CH3), 6.85e7.95 (11H, m, H-Ar);
dC (75 MHz, DMSO-d6) 16.7, 79.4, 112.8, 113.3, 121.8, 123.5, 125.0,