Ultrasound-assisted one-pot, four component synthesis of 4-aryl 3,4-dihydropyridone derivatives

Ultrasonics Sonochemistry

Volumn 18, Issue 1, 2011, Pages 32-36

  Ruiz, Enrique ^a   Rodríguez, Hortensia ^a   Coro, Julieta ^a   Salfrán, Esperanza ^a   Suárez, Margarita ^a   Martínez Alvarez, Roberto ^b   Martín, Nazario ^b  

^a Universidad de La Habana   (Cuba)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

3,4 Dihydropyridone derivatives; Sonochemistry; Ultrasound irradiation

Indexed keywords

SONOCHEMISTRY; ULTRASONICS;

ACETOACETATES; AMMONIUM ACETATE; AROMATIC ALDEHYDE; COMPONENT SYNTHESIS; CONVENTIONAL METHODS; GLACIAL ACETIC ACID; MELDRUM'S ACIDS; ULTRASOUND IRRADIATION;

IRRADIATION;

4 ARYL 3,4 DIHYDROPYRIDONE DERIVATIVE; ACETIC ACID; ACETOACETIC ACID; ACID; ALDEHYDE; AMMONIUM ACETATE; DIPYRONE; MELDRUM ACID; UNCLASSIFIED DRUG;

ARTICLE; PRIORITY JOURNAL; SYNTHESIS; ULTRASOUND;

EID: 77956421360     PISSN: 13504177     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ultsonch.2010.04.009     Document Type: Article

References (53)

1. Nuchter M., Ondruschka B., Jungnickel A., Muller U. Organic processes initiated by non-classical energy sources. J. Phys. Org. Chem. 2000, 13:579.
2. Mason T.J., Lorimer J.P. Sonochemistry. Part 1. The physical aspects. Chem. Soc. Rev. 1987, 16:239.
3. Li J.T., Wang S.X., Chen G.F., Li T.S. Some applications of ultrasound irradiation in organic synthesis. Curr. Org. Synth. 2005, 2:415.
4. Cravotto G., Cintas P. Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications. Chem. Soc. Rev. 2006, 35:180.
5. Mason T.J., Cintas P. Handbook of Green Chemistry and Technology 2002, 372. Blackwell Science, Oxford. J. Clark, D. Macquarrie (Eds.).
6. Cella R., Stefani H. Ultrasound in heterocycles chemistry. Tetrahedron 2009, 65:2619.
7. Muravyova E.A., Desenko S.M., Musatov V.I., Knyazeva I.V., Shishkina S.V., Shishkin O.V., Chebanov V.A. Ultrasonic-promoted three-component synthesis of some biologically active 1,2,5,6-tetrahydropyrimidines. J. Comb. Chem. 2007, 9:797.
8. 3 under ultrasound irradiation. Synth. Commun. 2004, 34:4565.
9. Jin T.S., Zhang J.S., Wang A.Q., Li T.S. Ultrasound-assisted synthesis of 1,8-dioxoocta hydroxanthene derivatives catalyzed by p-dodecylbenzenesulfonic acid in aqueous media. Ultrason. Sonochem. 2006, 13:220.
10. Guzen K.P., Cella R., Stefani H.A. Ultrasound enhanced synthesis of 1,5-benzodiazepinic heterocyclic rings. Tetrahedron Lett. 2006, 47:8133.
11. Tu S., Cao L., Zhang Y., Shao Q., Zhou D., Li C. An efficient synthesis of pyrido[2, 3-d]pyrimidine derivatives and related compounds under ultrasound irradiation without catalyst. Ultrason. Sonochem. 2008, 15:217.
12. 3H under ultrasound irradiation. Ultrason. Sonochem. 2003, 10:119.
13. El-Rahman N.M.A., Saleh T.S., Mady M.F. Ultrasound assisted synthesis of some new 1,3,4-thiadiazole and bi(1,3,4-thiadiazole) derivatives incorporating pyrazolone moiety. Ultrason. Sonochem. 2009, 16:70.
14. Zang H., Zhang Y., Zhang Y., Cheng B.W. An efficient ultrasound-promoted method for the one-pot synthesis of 7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one derivatives. Ultrason. Sonochem. 2010, 17:495.
15. Rigby J.H. Vinyl isocyanates as useful building blocks for alkaloid synthesis. Synlett 2000, 1.
16. De Clercq E. Perspectives of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection. Farmaco 1999, 54:26.
17. Parreira R.L.T., Abrahao O., Galembeck S.E. Conformational preferences of non-nucleoside HIV-1 reverse transcriptase inhibitors. Tetrahedron 2001, 57:3243.
18. Pastelin G., Mendez R., Kabela E., Farah A. The search for a digitalis substitute II. Milrinone (Win 47203) its action on the heart-lung preparation of the dog. Life Sci. 1983, 33:1787.
19. Presti E.L., Boggia R., Feltrin A., Menozzi G., Dorigo P., Mosti L. 3-Acetyl-5-acylpyridin-2(1H)-ones and 3-acetyl-7,8-dihydro-2, 5(1H, 6H)-quinolinediones: synthesis, Cardiotonic activity and computational studies. Farmaco 1999, 54:465.
20. Dorigo P., Fraccarolo D., Gaion R.M., Santostasi G., Borea P.A., Floreani M., Mosti L., Maragno I. New inotropic agents: milrinone analogs. Gen. Pharm. 1997, 28:781.
21. Altomare C., Cellamare S., Summo L., Fossa P., Mosti L., Carotti A. Ionization behavior and tautomerism-dependent lipophilicity of pyridine-2(1H)-one cardiotonic agents. Bioorg. Med. Chem. 2000, 8:909.
22. Anderson W.K., Dean D.C., Endo T. Vinylogous carbinolamine tumor inhibitors. 24. Synthesis, chemistry, and antineoplastic activity of α-halopyridinium salts: potential pyridone prodrugs of acylated vinylogous carbinolamine tumor inhibitors. J. Med. Chem. 1990, 33:1667.
23. S.B. Margolin, Inhibition of tumor necrosis factor α by N-substituted pyridines, US Patent 5,962,478, 1999.
24. Li Q., Mitscher L.A., Shen L.L. The 2-pyridone antibacterial agents: bacterial topoisomerase inhibitors. Med. Res. Rev. 2000, 20:231.
25. Dragovich P.S., Prins T.J., Zhou R., Brown E.L., Maldonado F.C., Fuhrman S.A., Zalman L.S., Tuntland T., Lee C.A., Patick A.K., Matthews D.A., Hendrickson T.S., Kosa M.B., Liu B., Batugo M.R., Gleeson J.P.R., Sakata S.K., Chen L., Guzman M.C., Meador J.W., Ferre R.A., Worland S.T. Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 6. Structure-activity studies of orally bioavailable, 2-pyridone-containing peptidomimetics. J. Med. Chem. 2002, 45:1607.
26. Dragovich P.S., Prins T.J., Zhou R., Johnson T.O., Brown E.L., Maldonado F.C., Fuhrman S.A., Zalman L.S., Patick A.K., Matthews D.A., Hou X., Meador J.W., Ferre R.A., Worland S.T. Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. Part 7: structure-activity studies of bicyclic 2-pyridone-containing peptidomimetics. Bioorg. Med. Chem. Lett. 2002, 12:733.
27. Patankar S.J., Jurs P.C. Prediction of glycine/NMDA receptor antagonist inhibition from molecular structure. J. Chem. Inf. Comput. Sci. 2002, 42:1053.
28. Morales A., Ochoa E., Suárez M., Verdecia Y., González L., Martín N., Quinteiro M., Seoane C., Soto J.L. Novel hexahydrofuro[3,4-b]-2(1H)-pyridones from 4-aryl substituted 5-alkoxycarbonyl-6-methyl-3,4-dihydropyridones. J. Heterocycl. Chem. 1996, 33:103.
29. Ochoa E., Suárez M., Verdecia Y., Pita B., Martin N., Quinteiro M., Seoane C., Soto J.L. Structural study of 3,4-dihydropyridones and furo[3,4-b]-2(1H)-pyridones as potential calcium channel modulators. Tetrahedron 1998, 54:12409.
30. Suárez M., Ochoa E., Verdecia Y., Pita B., Moran L., Martín N., Quinteiro M., Seoane C., Soto J.L., Novoa H., Blaton R., Peeters O., De Ranter C. Synthesis and structural study of 3,4-dihydro-2(1H)-pyridones and isoxazolo[5,4-b]pyridin-6(7H)-ones. Eur. J. Org. Chem. 2000, 2079.
31. Rodríguez H., Reyes O., Suárez M., Garay H., Pérez R., Cruz J., Verdecia Y., Martín N., Seoane C. Solid-phase synthesis of 4-aryl substituted 5-carboxy-6-methyl-3,4-dihydropyridones. Tetrahedron Lett. 2002, 43:439.
32. Rodríguez H., Martín O., Ochoa E., Suárez M., Reyes O., Garay H., Albericio F., Martín N. Solid-phase synthesis and structural study of substituted 1,4,5,6-tetrahydro-6-oxopyridine-3-carboxylic acids. QSAR Comb. Sci. 2006, 25:921.
33. Rodríguez H., Suárez M., Pérez R., Petit A., Loupy A. Solvent-free synthesis of 4-aryl substituted 5-alkoxycarbonyl-6-methyl-3,4-dihydropyridones under microwave irradiation. Tetrahedron Lett. 2003, 44:3709.
34. Verdecia Y., Suárez M., Morales A., Rodríguez E., Ochoa E., González L., Martín N., Quinteiro M., Seoane C., Soto J.L. Synthesis of methyl 4-aryl-6-methyl-47-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylates from methyl 4-aryl-6-methyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylates. J. Chem. Soc. Perkin Trans. 1996, 1:947.
35. Suárez M., Ochoa E., Pita B., Espinosa R., González L., Martín N., Quinteiro M., Seoane C., Soto J.L. Synthesis and structural characterization of substituted thieno[23-b]pyridines from o-chloroformyl-14-dihydropyridines. J. Heterocycl. Chem. 1997, 34:931.
36. Suárez M., Verdecia Y., Illescas B., Martínez-Álvarez R., Álvarez A., Ochoa E., Seoane C., Kayali N., Martín N. Synthesis and study of novel fulleropyrrolidines bearing biologically active 1,4-dihydropyridines. Tetrahedron 2003, 59:9179.
37. Suárez M., Novoa H., Verdecia Y., Ochoa E., Álvarez, Pérez R., Martínez-Álvarez R., Molero D., Seoane C., Blaton N., Peeters O., Martín N. A straightforward synthesis and structure of unprecedented iminium salts of dihydropyrido[3,2-e][13]thiazines. Tetrahedron 2006, 62:1365.
38. Alvarez A., Suárez M., Verdecia Y., Ochoa E., Barried B., Pérez R., Díaz M., Martínez R., Molero D., Seoane C., Novoa H., Blaton N., Peeters O., Martín N. Synthesis and structural study of semicarbazone-containing 1,4-dihydropyridine. Heterocycles 2006, 68:1631.
39. Martínez-Álvarez M.Suárez, Martin N., Verdecia Y., Ochoa E., Alba L., Seoane C., Kayali N. Electrospray ionisation and ion-trap fragmentation of substituted 3,4-dihydro-2(1H)-pyridin-2-ones. Rapid Commun. Mass Spectrom. 2002, 16:749.
40. 13C spectral assignment of 2(1H)-pyridone derivatives. Magn. Reson. Chem. 2004, 42:704.
41. Singh J., Koul P., Summon P.S., Ajay L.R., Sharma T.K., Razdan Simple and efficient one-pot synthesis of 3,4-dihydro-2-pyridones via solid-supported Bi(III)nitrate catalyzed double Michael addition-azaannulation. J. Heterocycl. Chem. 2008, 45:349.
42. Niemczewski B. A comparison of ultrasonic cavitation intensity in liquids. Ultrasonics 1980, 18:107.
43. McNulty J., Steere J.A., Wolf S. The ultrasound promoted Knoevenagel condensation of aromatic aldehydes. Tetrahedron Lett 1998, 39:8013.
44. Manson T.J. Ultrasound in synthetic organic chemistry. Chem. Soc. Rev. 1997, 26:443.
45. Shaabani A., Rezayan A.H., Rahmati A., Sharifi M. Ultrasound-accelerated synthesis of 1,4-dihydropyridines in an ionic liquid. Monatsh Chem. 2006, 137:77.
46. Cintas P., Luche J.L. Green chemistry. Green Chem. 1999, 1:115.
47. Kumar A. Salt effects on Diels-Alder reaction kinetics. Chem. Rev. 2001, 101:1.
48. Welton T. Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem. Rev. 1999, 99:2071.
49. Wasserscheid P., Keim W. Ionic liquids - new "solutions" for transition metal catalysis. Angew. Chem. Int. Ed. 2000, 39:3772.
50. Sheldon R. Catalytic reactions in ionic liquids. Chem. Commun. 2001, 2399.
51. Li J.T., Yang W.Z., Wang S.X., Li S.H., Li T.S. Improved synthesis of chalcones under ultrasound irradiation. Ultrason. Sonochem. 2002, 9:237.
52. 3 under ultrasound irradiation. Ultrason. Sonochem. 2002, 9:159.
53. Wang S.X., Li X.W., Li J.T. Synthesis of N-alkoxyphthalimides under ultrasound irradiation. Ultrason. Sonochem. 2008, 15:33.