First application of hexaaquaaluminium(III) tetrafluoroborate as a mild, recyclable, non-hygroscopic acid catalyst in organic synthesis: a simple and efficient protocol for the multigram scale synthesis of 3,4-dihydropyrimidinones by Biginelli reaction

Tetrahedron

Volumn 66, Issue 19, 2010, Pages 3463-3471

  Litvić, Mladen ^a   Večenaj, Ivana ^a   Ladišić, Zrinka Mikuldaš ^a   Lovrić, Marija ^a   Vinković, Vladimir ^b   Filipan Litvić, Mirela ^a  

^a BELUPO Pharmaceuticals   (Croatia)

^b RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

3,4 Dihydropyrimidinone; Biginelli reaction; Condensation; Heterocycles; Hexaaquaaluminium(III) tetrafluoroborate

Indexed keywords

3,4 DIHYDROPYRIMIDINONE DERIVATIVE; ALDEHYDE DERIVATIVE; ALUMINUM DERIVATIVE; ESTER DERIVATIVE; HEXAAQUAALUMINIUM TETRAFLUOROBORATE; PYRIMIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIGINELLI REACTION; CATALYSIS; PRIORITY JOURNAL; REACTION ANALYSIS; RECYCLING; STEREOSPECIFICITY; SYNTHESIS;

EID: 77950692018     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.024     Document Type: Article

References (86)

1. Kappe C.O. Tetrahedron 49 (1993) 6938-6963
2. Biginelli P. Gazz. Chim. Ital. 23 (1893) 360-416
3. Kappe C.O. Eur. J. Med. Chem. 35 (2000) 1043-1052
4. Mayer T.U., Kapoor T.M., Haggarty S.J., King R.W., Schreiber S.L., and Mitchison T.J. Science 286 (1999) 971-974
5. Kapoor T.M., Mayer T.U., Coughlin M.L., and Mitchison T.J. J. Cell Biol. 150 (2000) 975-988
6. Hurst E.W., and Hull R. J. Med. Pharm. Chem. 3 (1961) 215-229
7. Ashok M., Holla B.S., and Kumari N.S. Eur. J. Med. Chem. 42 (2007) 380-385
8. Fewell S.W., Smith C.M., Lyon M.A., Dumitrescu T.P., Wipf P., Day B.W., and Brodsky J.L. J. Biol. Chem. 279 (2004) 51131-51140
9. Magerramov A.M., Kurbanova M.M., Abdinbekova R.T., Rzaeva I.A., Farzaliev V.M., and Allakhverdiev M.A. Russ. J. Appl. Chem. 79 (2006) 787-790
10. Carswell C.I., Plosker G.L., and Jarvis B. Drugs 62 (2002) 2075-2085
11. Heys L., Moore C.G., and Murphy P.J. Chem. Soc. Rev. 29 (2000) 57-67
12. Bewley C.A., Ray S., Cohen F., Collins S.K., and Overmann L.E. J. Nat. Prod. 67 (2004) 1319-1324
13. Kolosov M.A., Orlov V.D., Beloborodov D.A., and Dotsenko V.V. Mol. Diversity 13 (2009) 5-25
14. Cepanec I., Litvić M., Filipan-Litvić M., and Grüngold I. Tetrahedron 63 (2007) 11822-11827
15. Lu J., and Bai Y. Synthesis (2002) 466-470
16. Gohain M., Prajapati D., and Sandhu J.S. Synlett (2004) 235-238
17. Bose D.S., Fatima L., and Mereyala H.B. J. Org. Chem. 68 (2003) 587-590
18. Kumar K.A., Kasthuraiah M., Reddy C.S., and Reddy C.D. Tetrahedron Lett. 42 (2001) 7873-7875
19. Reddy C.V., Mahesh M., Raju P.V.K., Ramesh Babu T., and Narayana Reddy V.V. Tetrahedron Lett. 43 (2002) 2657-2659
20. Ranu B.C., Hajra A., and Jana U. J. Org. Chem. 65 (2000) 6270-6272
21. Sun Q., Wang Y.-q., Ge Z.-m., Cheng T.-m., and Li R.-t. Synthesis (2004) 1047-1051
22. Ramaliga K., Vijayalakshmi P., and Kaimal T.N.B. Synlett (2001) 863-865
23. Khodaei M.M., Salehi P., Zolfigol M.A., and Sirouszadeh S. Pol. J. Chem. 78 (2004) 385-388
24. Ma Y., Qian C., Wang L., and Yang M. J. Org. Chem. 65 (2000) 3864-3868
25. Varala R., Alam M.M., and Adapa S.R. Synlett (2003) 67-70
26. Bose D.S., Kumar R.K., and Fatima L. Synlett (2004) 279-282
27. Jin T.-S., Wang H.-X., Xing C.-Y., Li X.-L., and Li T.-S. Synth. Commun. 34 (2004) 3009-3016
28. Manjula A., Rao B.V., and Neelakantan P. Synth. Commun. 34 (2004) 2665-2671
29. Sabitha G., Reddy K.B., Yadav J.S., Shailaja D., and Sivudu K.S. Tetrahedron Lett. 46 (2005) 8221-8224
30. Debache A., Boumoud B., Amimour M., Belfaitah A., Rhouati S., and Carboni B. Tetrahedron Lett. 47 (2006) 5697-5699
31. Suzuki I., Suzumura Y., and Takeda K. Tetrahedron Lett. 47 (2006) 7861-7864
32. Kappe C.O., and Falsone S.F. Synlett (1998) 718-720
33. Zhu Y., Pan Y., and Huang S. Synth. Commun. 34 (2004) 3167-3174
34. Sabitha G., Reddy G.S.K.K., Reddy C.S., and Yadav J.S. Synlett (2003) 858-860
35. Cepanec I., Litvić M., Bartolinčić A., and Lovrić M. Tetrahedron 61 (2005) 4275-4280
36. Xu H., and Wang Y.-G. Indian J. Chem. 42B (2003) 2604-2607
37. Paraskar A.S., DewKar G.K., and Sudulai A. Tetrahedron Lett. 44 (2003) 3305-3308
38. Gong L.Z., Chen X.H., and Xu X.Y. Chem.-Eur. J. 13 (2007) 8920-8926
39. Litvić M., Cepanec I., and Vinković V. Heterocycl. Commun. 9 (2003) 385-390
40. Filipan-Litvić M., Litvić M., Cepanec I., and Vinković V. Molecules 12 (2007) 2546-2558
41. Litvić M., Cepanec I., Filipan M., Kos K., Bartolinčić A., Drušković V., Tibi M.M., and Vinković V. Heterocycles 65 (2005) 23-36
42. Filipan-Litvić M., Litvić M., Cepanec I., and Vinković V. ARKIVOC XI (2008) 96-103
43. Filipan-Litvić M., Litvić M., and Vinković V. Tetrahedron 64 (2008) 5649-5656
44. Filipan-Litvić M., Litvić M., and Vinković V. Tetrahedron 64 (2008) 10912-10918
45. Filipan-Litvić M., Litvić M., and Vinković V. Bioorg. Med. Chem. 16 (2008) 9276-9282
46. March J. Advanced Organic Chemistry. 4th ed. (1992), John Wiley & Sons, New York, NY
47. Saini A., Kumar S., and Sandhu J.S. Indian J. Chem. 46B (2007) 1690-1694
48. Williams D.B.G., and Lawton M.C. Green Chem. 10 (2008) 914-917
49. Williams D.B.G., and Lawton M. Org. Biomol. Chem. 3 (2005) 3269-3272
50. Sobhani S., and Tashrifi Z. Synth. Commun. 39 (2009) 120-131
51. Terblans Y.M., Huyser M., Young D.A., and Green M.J. Can. J. Chem. 84 (2006) 859-866
52. Chaminade X., Chiba S., Narasaka K., and Dunach E. Tetrahedron Lett. 49 (2008) 2384-2387
53. 3 in the presence of chiral ligands could possibly be used in enantioselective version of Biginelli reaction (see Ref. 36).
54. Bosacek V., Polak R., Kucera E., and Danes V. Collect. Czech. Chem. Commun. 27 (1962) 2575-2585
55. Kraus M., Kochloefl K., Komers R., and Bazant V. Collect. Czech. Chem. Commun. 24 (1959) 1188-1193
56. Weidenhoffer Z., and Hala S. Collect. Czech. Chem. Commun. 40 (1975) 560-567
57. Milnes M.H., and Dean R.E. J. Appl. Chem. Biotechnol. 21 (1971) 287-296
58. Kraus M., Kochloefl K., Beranek L., and Bazant V. Proc. Intern. Congr. Catalysis. 3rd ed. Vol. 1 (1965), North-Holland Publishing, Amsterdam 583-585
59. Schneider P., Kraus M., and Bazant V. Collect. Czech. Chem. Commun. 27 (1962) 9-16
60. Strnad P., and Kraus M. Collect. Czech. Chem. Commun. 30 (1960) 1136-1143
61. Takami, N.; Ishii, H. US Patent 2,003,059,684 (A1), Kabushiki Kaisha Toshiba, 2003.
62. Simon S. J. Optoelectr. Adv. Mater. 5 (2003) 147-152
63. Yusoff M.M.S., and Muslimin M. Malaysian J. Anal. Sci. 11 (2008) 262-268
64. Härting M., Woodford S., Knoesen D., Bucher R., and Britton D.T. Thin Solid Films 430 (2003) 153-156
65. Huang T., Wu Z., Xia B., Chen J., Yu X., Xu N., Lu C., and Yu H. Sci. Technol. Adv. Mater. 4 (2003) 491-494
66. Blackburn A.C., Gallucci J.C., and Gerkin R.E. Acta Crystallogr. C48 (1992) 1185-1188
67. Ramajothi J., and Dhanuskodi S. Cryst. Res. Technol. 38 (2003) 986-991
68. Part of the work has been presented as a poster: Litvić, M.; Večenaj, I.; Mikuldaš Ladišić, Z.; Lesjak, D.; Mlinarić, K.; Regović, M.; Glavanović, M.; Vizjak, M.; Filipan-Litvić, M.; Vinković, V. XXI Croatian Meeting of Chemists and Chemical Engineers, Split, Croatia, 2009, Book of abstracts, p 115.
69. Jenner G. Tetrahedron Lett. 45 (2004) 6195-6198
70. Folkers K., and Johnson T.B. J. Am. Chem. Soc. 55 (1933) 3784-3791
71. Sweet F., and Fissekis J.D. J. Am. Chem. Soc. 95 (1973) 8741-8749
72. Kappe C.O. J. Org. Chem. 62 (1997) 7201-7204
73. Cotton F.A., and Wilkinson G. Advanced Inorganic Chemistry. 5th ed. (1988), John Wiley & Sons, New York, NY pp 39-41
74. Wiberg N. Holleman-Wiberg's Inorganic Chemistry. 35th ed. (2001), Academic Press, London pp 1016
75. March J. Advanced Organic Chemistry. 4th ed. (1992), John Wiley & Sons, New York, NY p 263
76. Katakura R., and Koide Y. Chem. Lett. 34 (2005) 1448-1449
77. Yadav J.S., Reddy B.V.S., Srinivas R., Venugopal C., and Ramalingam T. Synthesis (2001) 1341-1345
78. Nasr-Esfahani M., Karami B., Montazerozohori M., and Abdi K. J. Heterocycl. Chem. 45 (2008) 1183-1185
79. Moran, M.M.; Fanger, C.; Chong, J.A.; Mcnamara, C.; Zhen, X.; Mandel-Brehm, J. WO 073,505 (A2), 2007, Hydra Biosciences.
80. Sabitha G., Reddy G.S.K.K., Reddy K.B., and Yadav J.S. Tetrahedron Lett. 44 (2003) 6497-6499
81. Reddy Y.T., Rajitha B., Reddy P.N., Kumar B.S., and Rao V.P. Synth. Commun. 34 (2004) 3821-3825
82. Shirini F., Zolfigol M.A., and Abri A.-R. J. Iran Chem. Soc. 5 (2008) 96-99
83. Singh K., Singh S., and Mahajan A. J. Org. Chem. 70 (2005) 6114-6117
84. Ramu E., Korta V., Bansal N., Varala R., and Adapa S.R. Rāsayan J. Chem. 1 (2008) 188-194
85. Dondoni A., and Masi A. Tetrahedron Lett. 42 (2001) 7975-7978
86. Desai B., Dallinger D., and Kappe C.O. Tetrahedron 62 (2006) 4651-4664