Microwave-assisted synthesis of pyrazolo[3,4-b]pyridine- spirocycloalkanediones by three-component reaction of 5-aminopyrazole derivatives, paraformaldehyde and cyclic β-diketones

Tetrahedron Letters

Volumn 51, Issue 36, 2010, Pages 4717-4719

  Quiroga, Jairo ^a   Trilleras, Jorge ^b   Pantoja, Dayana ^a   Abonía, Rodrigo ^a   Insuasty, Braulio ^a   Nogueras, Manuel ^c   Cobo, Justo ^c  

^a UNIVERSIDAD DEL VALLE   (Colombia)

^b UNIVERSIDAD DEL ATLÁNTICO   (Colombia)

^c UNIVERSITY OF JAÉN   (Spain)

Author keywords

Annulation; Cyclic diketones; Microwave; Multicomponent reaction; Solvent free reaction; Spiro compounds

Indexed keywords

1,3 DIKETONE; ALKANEDIOL DERIVATIVE; PARAFORMALDEHYDE; PHENYL GROUP; PYRAZOLE DERIVATIVE; PYRAZOLO[3,4 B]PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; CRYSTALLIZATION; CYCLIZATION; MICROWAVE RADIATION; ONE POT SYNTHESIS; POLYMERIZATION; X RAY DIFFRACTION;

EID: 77955468838     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.009     Document Type: Article

References (33)

1. G.J.T. Kuster, L.W.A. van Berkom, M. Kalmoua, A. van Loevezijn, L.A.J.M. Sliedregt, B.J. van Steen, C.G. Kruse, F.P.J.T. Rutjes, and H.W. Scheeren J. Comb. Chem. 8 2006 85 94
2. C. Macleod, B.I. Martinez-Teipel, W.M. Barker, and R.E. Dolle J. Comb. Chem. 8 2006 132 140
3. G. Lang, A. Pinkert, J.W. Blunt, and M.H.G. Munro J. Nat. Prod. 68 2005 1796 1798
4. C.A. Maier, and B. Wuensch J. Med. Chem. 45 2002 438 448
5. A. Shaabani, and A. Bazgir Tetrahedron Lett. 45 2004 2575 2577
6. A.P. Kadutskii, and N.G. Kozlov Synlett 19 2006 3349 3351
7. K.G. Nazarenko, N.A. Shtil, M.O. Lozinskii, and A.A. Tolmachev Tetrahedron 63 2007 7727 7732
8. K.A. Krasnov, and V.G. Kartsev Russ. J. Org. Chem. 41 6 2005 901 906
9. M. Rahimizadeh, A. Shiri, and M. Bakavoli Chin. Chem. Lett. 18 2007 689 693
10. M. Rolandsgard, S. Baldawi, D. Sirbu, V. Bjørnstad, C. Rømming, and K. Undheim Tetrahedron 61 2005 4129 4140
11. K. Arya, and A. Dandia J. Fluorine Chem. 128 2007 224 231
12. C. Marti, and E.M. Carrei Eur. J. Org. Chem. 2003 2209 2219
13. M.A.P. Martins, C.P. Frizzo, D.N. Moreira, L. Buriol, and P. Machado Chem. Rev. 109 2009 4140 4182
14. C.O. Kappe Angew. Chem., Int. Ed. 43 2004 6250 6284
15. J. Quiroga, J. Trilleras, B. Insuasty, R. Abonía, M. Nogueras, and J. Cobo Tetrahedron Lett. 49 2008 2689 2691
16. J. Quiroga, J. Trilleras, B. Insuasty, R. Abonía, M. Nogueras, A. Marchal, and J. Cobo Tetrahedron Lett. 49 2008 3257 3259
17. J. Quiroga, B. Insuasty, H. Insuasty, R. Abonía, A.J. Ortíz, A. Sánchez, and M. Nogueras J. Heterocycl. Chem. 38 2001 339 341
18. J. Quiroga, A. Hormaza, B. Insuasty, A.J. Ortíz, A. Sánchez, and M. Nogueras J. Heterocycl. Chem. 35 1998 231 233
19. J. Quiroga, S. Cruz, B. Insuasty, R. Abonía, P. Hernandez, A. Bolaños, and R. Moreno J. Heterocycl. Chem. 35 1998 333 338
20. V.D. Orlov, J. Quiroga, and N.N. Kolos Khim. Geterosikl. Soedin. 1987 1247 1251 CA: 88, 167373
21. J. Quiroga, J. Portilla, H. Serrano, R. Abonía, B. Insuasty, M. Nogueras, and J. Cobo Tetrahedron Lett. 48 2007 1987 1990
22. J. Quiroga, D. Cobo, B. Insuasty, R. Abonía, S. Cruz, M. Nogueras, and J. Cobo J. Heterocycl. Chem. 45 2008 155 159
23. J. Quiroga, J. Trilleras, A.I. Sánchez, B. Insuasty, R. Abonía, M. Nogueras, and J. Cobo Lett. Org. Chem. 6 2009 381 383
24. J. Quiroga, S. Cruz, B. Insuasty, R. Abonía, M. Nogueras, and J. Cobo Tetrahedron Lett. 47 2006 27 30
25. J.N. Low, J. Cobo, J. Mera, J. Quiroga, and C. Glidewell Acta Crystallogr., Sect. C 60 2004 265 269
26. J.N. Low, G. Ferguson, J. Cobo, M. Nogueras, S. Cruz, J. Quiroga, and C. Glidewell Acta Crystallogr., Sect. C 60 2004 438 443
27. J.C. Castillo, R. Abonía, J. Cobo, and C. Glidewell Acta Crystallogr., Sect. C 65 2009 303 310
28. J. Trilleras, S. Cruz, J. Cobo, J.N. Low, and C. Glidewell Acta Crystallogr., Sect. C 64 2008 671 674
29. J. Trilleras, J. Quiroga, J. Cobo, J.N. Low, and C. Glidewell Acta Crystallogr., Sect. C 64 2008 665 670
30. S. Cruz, J. Trilleras, J. Cobo, J.N. Low, and C. Glidewell Acta Crystallogr., Sect. C C64 2008 637 642
31. General procedure to the synthesis of pyrazolopyridine-5-spiro derivatives 4, 5 and 6. Microwave method: Microwave experiment was carried out using a focused microwave reactor (CEM Discover TM). A mixture of amine (2 mmol), cyclic β-diketone (2 mmol of 5,5-dimethylcyclohexane-1,3-dione, cyclohexane-1,3-dione, cyclopentane-1,3-dione or indandione) and an excess of paraformaldehyde (30 mol %) was exposed to microwave radiation for 25 min at 200 °C and a maximum power of 300 W. The reaction mixture was dissolved in hot ethanol. After cooling down to room temperature, the solid product was filtered and washed with fresh ethanol and hexanes (2 × 5 mL) to afford a pure product. Conventional method: A solution of amine (2 mmol), cyclic β-diketone (2 mmol of 5,5-dimethylcyclohexane-1,3-dione, cyclohexane-1,3-dione, cyclopentane-1,3-dione or indandione) in ethanol (15 mL), was added to an excess of paraformaldehyde (30 mol %) and the mixture was heated under reflux for 24 h. After cooling down to rt, the colourless precipitate was filtered off, washed with ethanol (2 × 5 mL) and dried to afford the pure products. In the case of the reaction between indandione and all 5-aminopyrazoles derivatives 1, the compound 7 was obtained in a yield of 45% in each reaction after separating by column chromatography using chloroform as the eluent.
32. C. Simon, T. Constantieux, and J. Rodriguez Eur. J. Org. Chem. 2004 4957 4980
33. -1 2963 (CH st), 1721-1700 (CO st).