Solvent-free synthesis of functionalized pyridine derivatives using Wells-Dawson heteropolyacid as catalyst

Tetrahedron Letters

Volumn 52, Issue 34, 2011, Pages 4412-4416

  Sanchez, Laura M ^a   Sathicq, Ángel G ^a   Jios, Jorge L ^b   Baronetti, Graciela T ^c   Thomas, Horacio J ^d   Romanelli, Gustavo P ^a  

^a DEPARTAMENTO DE QUÍMICA   (Argentina)

^b FACULTAD DE CIENCIAS EXACTAS   (Argentina)

^c UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^d UNLP CICPBA   (Argentina)

Author keywords

3 Formylchromones; Functionalized pyridines; Multicomponent reaction; Solvent free organic synthesis; Wells Dawson heteropolyacid

Indexed keywords

AMMONIUM ACETATE; CHROMONE DERIVATIVE; ESTER DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; BIOCATALYST; POLYMERIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 79960834323     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.06.048     Document Type: Article

References (30)

1. J. Quiroga, A. Rengifo, B. Insuasty, R. Abonía, M. Nogueras, and A. Sánchez Tetrahedron Lett. 43 2002 9061 9063
2. G. Rihs, I. Sigg, G. Hass, and T. Winkler Helv. Chim. Acta 68 1985 1933 1935
3. W. Basinski Pol. J. Chem. 69 1995 376 384
4. J. Quiroga, D. Mejía, B. Insuasty, R. Abonía, M. Nogueras, A. Sánchez, J. Cobo, and J. Low J. Heterocyclic Chem. 35 2002 51 54
5. W. Busse, B. Garthoff, and F. Seuter Dihydropyridines: progress in pharmacology and therapy 1993 Springer
6. G. Swarnalatha, G. Prasanthi, N. Sirisha, and C. Madhusudhana Chetty Int. J. Chem. Tech., Res. 3 2011 75 89
7. A. Sausins, and G. Duburs Chem. Heterocycl. Compd. 28 1992 363 391
8. M. Satyanarayana Reddy, G.L.D. Krupadanam, and G. Srimannarayana Indian J. Chem., Sect. B 29B 1990 978 979
9. K. Goerlitzer, and K. Michels Arch. Pharm. 321 1988 567 568
10. Ch. Ghosh, S. Karak, and A. Patra J. Chem. Res. 311-313 2002 741 751
11. Ch. Ghosh, A. Ray, and A. Patra J. Heterocycl. Chem. 38 2001 1459 1463
12. A. Sathicq, G. Romanelli, A. Ponzinibbio, G. Baronetti, and H. Thomas Lett. Org. Chem. 7 2010 511 518
13. M. Terzidis, J. Stephanidou, C. Tsoleridis, A. Terzis, C. Raptopoulou, and V. Psycharis Tetrahedron 66 2010 947 954 and references cited herehin
14. D. Horton, G. Bourne, and M. Smythe Chem. Rev. 103 2003 893 930
15. V. Sosnovskikh, V. Moshkin, and M. Kodess Tetrahedron Lett. 49 2008 6856 6859
16. I. Bassoude, S. Berteina-Raboin, J.M. Leger, C. Jarry, E.M. Essassi, and G. Guillaumet Tetrahedron 67 2011 2279 2286
17. M. Lácová, A. Puchala, E. Solčanyova, J. Lac, P. Koiš, J. Chovancova, and D. Rasala Molecules 10 2005 809 821
18. J. Quiroga, J. Portilla, R. Abonia, B. Insuasty, M. Nogueras, and J. Cobo Tetrahedron Lett. 49 2008 6254 6256
19. A.S. Plaskon, S.V. Ryabukhin, D.M. Volochnyuk, K.S. Gavrilenko, A.N. Shivanyuk, and A.A. Tolmachev J. Org. Chem. 73 2008 6010 6013
20. M.A. Ibrahim, T.E. Ali, Y.A. Alnamer, and Y.A. Gabr ARKIVOC i 2010 98 135
21. V.Ya. Sosnovskikh, and B.I. Usachev Mendeleev Commun. 2000 240
22. V.Ya. Sosnovskikh, and B.I. Usachev Russ. Chem. Bull. 50 2001 1426 1429
23. 27,28 General Procedures for the preparation of substituted pyridines. The solid catalyst (1 mmol %) was added to a mixture of 3-formylchromones (1 mmol), alkyl or aryl acetylacetates (1 mmol) and ammonium acetate (1 mmol). The mixture was stirred at 80 °C for the indicated time (Table 1). The progress of the reaction was monitored by TLC. After completion of the reaction, hot toluene was added (2 × 2.5 mL) and the catalyst was filtered. The extracts were combined; their solvents were evaporated and then concentrated in vacuum. All the solid crude products were recrystallized.
24. L. Shen, S. Cao, J. Wu, J. Zhang, H. Li, N. Liu, and X. Qian Green Chem. 11 2009 1414 1420
25. G. Haas, J.L. Stanton, A. Von Sprecher, and P. Wenk J. Heterocycl. Chem. 18 1981 607 612
26. G. Baronetti, L. Briand, U. Sedran, and H. Thomas Appl. Catal. A:Gen 172 2 1998 265 272
27. D.K. Lyon, W.K. Miller, T. Novet, P.J. Domaille, E. Evitt, D.C. Johnson, and R.G. Finke J. Am. Chem. Soc. 113 19 1991 7209 7221
28. Recycling of catalyst. After reaction, the catalyst was washed with toluene (2 × 2 mL), dried under vacuum, and reused in the next catalytic cycle.
29. 3) δ 1.09 (t, J = 7 Hz, 3H), 4.20 (q, J = 7 Hz, 2H), 6.94 (dt, J = 8 and 2 Hz, 1H), 7.11(d, J = 8 Hz, 1H), 7.43-7.53 (m, 3H), 7.54-7.67 (m, 4H), 8.41 (d, J = 2 Hz, 1H), 9.04 (d, J = 2 Hz, 1H), 11.81 (s, 1H).
30. M. Satyanarayana Reddy, G.L.D. Krupadanam, and G. Srimannarayarta Indian J. Chem. 29B 1990 978 979