Citation: Rupali L. Magar, Prashant B. Thorat, Pratima B. Thorat, Vinod V. Thorat, Bhagawan R. Patil, Rajendra P. Pawar. Distereoselective one-pot synthesis of pyrimidopyrimidines using sulfated tin oxide as a reusable catalyst: An extension of Biginelli-type reaction[J]. Chinese Chemical Letters, ;2013, 24(12): 1070-1074. shu

Distereoselective one-pot synthesis of pyrimidopyrimidines using sulfated tin oxide as a reusable catalyst: An extension of Biginelli-type reaction

1.
a Department of Chemistry, Deogiri College, Aurangabad 431005, MS, India;
2.
b Department of Chemistry, Dnyanopasak College, Parbhani 431401, MS, India;
3.
c Department of Chemistry, Sharda Mahavidyalaya, Parbhani 431401, MS, India

Corresponding author: Rajendra P. Pawar,
Received Date: 23 April 2013
Available Online: 17 June 2013

The Biginelli-type compounds 4,5,8a-triarylhexahydropyrimido[4,5-d]pyrimidine-2,7(1H,3H)-diones were synthesized by a one-pot three-component reaction using sulfated tin oxide as a reusable catalyst. This method has the advantages of high yields, short reaction time, simple starting materials and reusability of catalyst for several times.
- Biginelli-type reaction,
- Multicomponent reactions,
- Pyrimido[4,5-d]pyrimidine,
- Sulfated tin oxide,
- Reusable catalyst
1. [1]
  [1] (a) C.C.A. Cariou, G.J. Clarkson, M. Shipman, Rapid synthesis of 1,3,4,4-tetrasubstituted b-lactams from methyleneaziridines using a four-component reaction, J. Org. Chem. 73 (2008) 9762-9764;
2. [2]
  (b) H.R. Shaterian, H. Yarahmadi, M. Ghashang, Silica supported perchloric acid (HClO₄-SiO₂): an efficient and recyclable heterogeneous catalyst for the one-pot synthesis of amidoalkyl naphthols, Tetrahedron 64 (2008) 1263-1269;
3. [3]
  (c) A. Znabet, E. Ruijter, F.J.J. de Kanter, et al., Highly stereoselective synthesis of substituted prolyl peptides using a combination of biocatalytic desymmetrization and multicomponent reactions, Angew. Chem. Int. Ed. 49 (2010) 5289-5292.
4. [4]
  [2] (a) A. Domling, I. Ugi, Multicomponent reactions with isocyanides, Angew. Chem. Int. Ed. 39 (2000) 3168-3210;
5. [5]
  (b) S. Heck, A.A. Domling, Versatile multi-component one-pot thiazole synthesis, Synlett 3 (2000) 424-426.
6. [6]
  [3] I. Ugi, A. Domling, Multicomponent reactions in organic chemistry, Endeavour 18 (1994) 115-122.
7. [7]
  [4] (a) E.M. Gordan, R.W. Barrett,W.J. Dower, S.P.A. Fodor,M.A. Gallop, Application of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies and future directions, J. Med. Chem. 37 (1994) 1385-1401;
8. [8]
  (b) A.A. Virgilio, J.A. Ellman, Simultaneous solid-phase synthesis of β-turn mimetics incorporating side-chain functionality, J. Am. Chem. Soc. 116 (1994) 11580-11581;
9. [9]
  (c) S.M. Freier, D.A.M. Konings, J.R. Wyatt, D.J. Ecker, Deconvolution of combinatorial libraries for drug discovery: a model system, J. Med. Chem. 38 (1995) 344-352.
10. [10]
  [5] (a) E.K. Kick, J.A. Ellman, Expedient method for the solid-phase synthesis of aspartic acid protease inhibitors directed toward the generation of libraries, J. Med. Chem. 38 (1995) 1427-1430;
11. [11]
  (b) D.A. Campbell, J.C. Bermak, T.S. Burkoth, D.V. Patel, A transition state analog inhibitor combinatorial library, J. Am. Chem. Soc. 117 (1995) 5381-5382.
12. [12]
  [6] A.S. Jones, J.R. Sayers, R.T. Walker, E.D. Clercq, Synthesis and antiviral properties of (E)-5-(2-bromovinyl)-2'-deoxycytidine-related compounds, J. Med. Chem. 31 (1988) 268-271.
13. [13]
  [7] M.B. Deshmukh, S.M. Salunkhe, D.R. Patil, P.V. Anbhule, A novel and efficient one step synthesis of 2-amino-5-cyano-6-hydroxy-4-aryl pyrimidines and their antibacterial activity, Eur. J. Med. Chem. 44 (2009) 2651-2655.
14. [14]
  [8] C. Gasse, D. Douguet, V. Huteau, et al., Substituted benzyl-pyrimidines targeting thymidine monophosphate kinase of Mycobacterium tuberculosis: synthesis and in vitro anti-mycobacterial activity, Bioorg. Med. Chem. 16 (2008) 6075-6085.
15. [15]
  [9] R. Lin, S.G. Johnson, P.J. Connolly, et al., Synthesis and evaluation of 2,7-diaminothiazolo[ 4,5-d]pyrimidine analogues as anti-tumor epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors, Bioorg. Med. Chem. Lett. 19 (2009) 2333-2340.
16. [16]
  [10] E.P.S. Falcao, S.J. Melo, R.M. Srivastava, M.T.J.A. Catanho, S.C. Nascimento, Synthesis and antiinflammatory activity of 4-amino-2-aryl-5-cyano-6-{3- and 4-(Nphthalimidophenyl)} pyrimidines, Eur. J. Med. Chem. 41 (2006) 276-282.
17. [17]
  [11] Q. Chen, X.L. Zhu, L.L. Jiang, Z.M. Liu, G.F. Yang, Synthesis, antifungal activity and CoMFA analysis of novel 1,2,4-triazolo[1,5-a]pyrimidine derivatives, Eur. J. Med. Chem. 43 (2008) 595-603.
18. [18]
  [12] G.W. Rewcastle, A.J. Bridges, D.W. Fry, J.R. Rubin, W.A. Denny, Tyrosine kinase inhibitors. 12. Synthesis and structure-activity relationships for 6-substituted 4- (phenylamino)pyrimido[5,4-d]pyrimidines designed as inhibitors of the epidermal growth factor receptor, J. Med. Chem. 40 (1997) 1820-1826.
19. [19]
  [13] (a) D. Prajapati, P.P. Baruah, B.J. Gogoi1, J.S. Sandhu, One-pot synthesis of novel 1H-pyrimido[4,5-c] [1,2]diazepines and pyrazolo [3,4-d]pyrimidines Beilstein, J. Org. Chem. 2 (2006) 5, http://dx.doi.org/10.1186/1860-5397-2-5;
20. [20]
  (b) A. Bazgira, M.M. Khanaposhtani, A.A. Soorki, One-pot synthesis and antibacterial activities of pyrazolo[4',3':5,6]pyrido[2,3-d]pyrimidine-dione derivatives, Bioorg. Med. Chem. Lett. 18 (2008) 5800-5803.
21. [21]
  [14] P. Biginelli, Aldehyde-urea derivatives of aceto- and oxaloacetic acids, Gazz. Chim. Ital. 23 (1893) 360-413.
22. [22]
  [15] F. Shi, R. Jia, X. Zhang, et al., Extension of the Biginelli-type reaction: one-pot synthesis of pyrimidopyrimidines and spirobi[pyrimidine]s using potassium hydrogen sulfate as a catalyst, Synthesis 18 (2007) 2782-2790.
23. [23]
  [16] P. Sharma, N. Rane, V.K. Gurram, Synthesis and QSAR studies of pyrimido[4,5- d]pyrimidine-2,5-dione derivatives as potential antimicrobial agents, Bioorg. Med. Chem. Lett. 14 (2004) 4185-4190.
24. [24]
  [17] M. Dabiri, H. Arvin-Nezhad, H.R. Khavasi, A. Bazgir, Microwave-induced perchloric acid catalyzed novel solvent-free synthesis of 4-aryl-3,4-dihydropyrimidones via Biginelli condensation, J. Heterocycl. Chem. 44 (2007) 1009-1011.
25. [25]
  [18] (a) M. Hino, K. Atata, Synthesis of solid superacid catalyst with acid strength of H₀≤ -16.04, J. Chem. Soc. Chem. Commun. 18 (1980) 851-852;
26. [26]
  (b) E. Igiesia, S.L. Sale, G.M. Kramer, Isomerization of alkanes on sulfated zirconia: promotion by Pt and by adamantyl hydride transfer species, J. Catal. 144 (1993) 238-253.
27. [27]
  [19] (a) B.M. Reddy, P.M. Sreekanth, P. Lakshmanan, Sulfated zirconia as an efficient catalyst for organic synthesis and transformation reactions, J. Mol. Cat. A: Chem. 237 (2005) 93-100;
28. [28]
  (b) B.M. Reddy, P.M. Sreekanth, An efficient synthesis of 1,5-benzodiazepine derivatives catalyzed by a solid superacid sulfated zirconia, Tetrahedron Lett. 44 (2003) 4447-4449;
29. [29]
  (c) X.B. Li, N. Katsutoshi, J.S. Laurent, O. Roberta, A.L. Johannes, Influence of calcination procedure on the catalytic property of sulfated zirconia, Catal. Lett. 113 (2007) 34-40.
30. [30]
  [20] J.C. Yori, M.A. Amato, G. Costa, J.M. Perera, Isomerization of n-butane on Pt/So₄^2--ZrO₂ and mechanical mixtures of Pt/Al₂O₃ + SO₄^2--ZrO₂, J. Catal. 153 (1995) 218-223.
31. [31]
  [21] (a) A.I. Ahmed, S.A. El-Hakam, A.S. KHder, W.S.A. El-Yazeed, Nanostructure sulfated tin oxide as an efficient catalyst for the preparation of 7-hydroxy-4- methyl coumarin by Pechmann condensation reaction, J. Mol. Cat. A: Chem. 366 (2013) 99-108;
32. [32]
  (b) T. Suzuki, T. Yokoi, R. Otomo, J.N. Kondo, T. Tatsumi, Dehydration of xylose over sulfated tin oxide catalyst: influences of the preparation conditions on the structural properties and catalytic performance, Appl. Catal. A: Gen. 408 (2011) 117-124.
33. [33]
  [22] (a) S.R. Sarda, V.B. Puri, A.B. Rode, et al., Sulfated tin oxides: a suitable reagent for synthesis of 2,4-diphenyl-4,6,7,8-tetrahydrochromen-5-one, Arkivoc 16 (2007) 246-251;
34. [34]
  (b) S.A. Dake, M.B. Khedkar, G.S. Irmale, et al., Sulfated tin oxide: a reusable and highly efficient heterogeneous catalyst for the synthesis of 2,4,5-triaryl-1Himidazole derivatives, Synth. Commun. 42 (2012) 1509-1520.
35. [35]
  [23] R.L. Magar, P.B. Thorat, V.B. Jadhav, et al., Silica gel supported polyamine: a versatile catalyst for one pot synthesis of 2-amino-4H- chromene derivatives, J. Mol. Cat. A: Chem. 374-375 (2013) 118-124.
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