A Rapid and Green Method for Solvent-Free Synthesis of 1,8-Dioxodecahydroacridines Using Tetrabutylammonium Hexatungstate as a Reusable Heterogeneous Catalyst

doi:10.1016/S1872-2067(11)60449-X

Abstract

Abstract: Tetrabutylammonium hexatungstate, [TBA]₂[W₆O₁₉], has been used as an efficient, inexpensive, and recyclable green catalyst for the one-pot three-component synthesis of 1,8-dioxodecahydroacridines by the reaction of dimedone with aromatic or aliphatic aldehydes in the presence of a nitrogen source (ammonium acetate or aromatic amines) under neat conditions. There are several advantages to the current process over the standard procedures available in the literature, including shorter reaction times (7–14 min), higher yields, facile work-up, and minimal environmental impact. Furthermore, the catalyst can be conveniently recovered and reused.

Key words: 1,8-dioxodecahydroacridine, solvent-free condition, tetrabutylammonium hexatungstate

Abolghasem DAVOODNIA, Atefeh ZARE-BIDAKI, Hossein BEHMADI. A Rapid and Green Method for Solvent-Free Synthesis of 1,8-Dioxodecahydroacridines Using Tetrabutylammonium Hexatungstate as a Reusable Heterogeneous Catalyst[J]. Chinese Journal of Catalysis, 2012, 33(11): 1797-1801.

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References

1 Sirisha K, Bikshapathi D, Achaiah G, Reddy V M. Eur J Med Chem, 2011, 46: 1564
2 Solanki M J, Vachharajani P R, Dubal G G, Shah V H. Int J ChemTech Res, 2011, 3: 1139
3 Ogawa T, Nakato A, Tsuchida K, Hatayama K. Chem Pharm Bull, 1993, 41: 108
4 Sirisha K, Achaiah G, Reddy V M. Arch Pharm, 2010, 343: 342
5 Jain S M, Kant R, Devi S, Dahr K L, Singh S, Bani S, Singh G B. Indian J Chem Sect B, 1990, 29: 95
6 Furuta T, Shibata S, Kodama I, Yamada K. J Cardiovasc Pharmacol, 1983, 5: 836
7 Laurent S, Brisac A M, Champeroux P, Lacolley P, Huguet F, Legrand M, Lucet B, Tsoucaris D, Briand V, Schmitt H. Fun-dam Clin Pharm, 1989, 3: 47
8 Hilgeroth A, Billich A, Lilie H. Eur J Med Chem, 2001, 36: 367
9 Hilgeroth A, Dressler C, Neuhoff S, Spahn-Langguth H, Langguth P. Pharmazie, 2000, 55: 784
10 Dabiri M, Baghbanzadeh M, Arzroomchilar E. Catal Commun, 2008, 9: 939
11 Chandrasekhar S, Rao Y S, Sreelakshmi L, Mahipal B, Reddy C R. Synthesis, 2008: 1737
12 Shen W, Wang L M, Tian H, Tang J, Yu J J. J Fluorine Chem, 2009, 130: 522
13 Balalaie S, Chadegani F, Darviche F, Bijanzadeh H R. Chin J Chem, 2009, 27: 1953
14 Venkatesan K, Pujari S S, Srinivasan K V. Synth Commun, 2009, 39: 228
15 Das B, Thirupathi P, Mahender I, Reddy V S, Rao Y K. J Mol Catal A, 2006, 247: 233
16 Fan X, Li Y, Zhang X, Qu G, Wang J. Heteroat Chem, 2007, 18: 786
17 Niknam K, Panahi F, Saberi D, Mohagheghnejad M. J Het-erocyclic Chem, 2010, 47: 292
18 Rashedian F, Saberib D, Niknam K. J Chin Chem Soc, 2010, 57: 998
19 Martin N, Quinteiro M, Seoane C, Soto J L, Mora A, Suarez M, Ochoa E, Morales A, del Bosque J R. J Heterocycl Chem, 1995, 32: 235
20 Tu S, Miao C, Gao Y, Fang F, Zhuang Q, Feng Y, Shi D. Synlett, 2004: 255
21 Davoodnia A, Allameh S, Fazli S, Tavakoli-Hoseini N. Chem Pap, 2011, 65: 714
22 Gerard V S, Notheisz F. Heterogeneous Catalysis in Organic Chemistry. San Diego: Elsevier, 2000
23 Aoyama T, Takido T, Kodomari M. Synlett, 2004: 2307
24 Emrani A, Davoodnia A, Tavakoli-Hoseini N. Bull Korean Chem Soc, 2011, 32: 2385
25 Davoodnia A, Tavakoli-Nishaburi A, Tavakoli-Hoseini N. Bull Korean Chem Soc, 2011, 32: 635
26 Moghaddas M, Davoodnia A, Heravi M M, Tavakoli-Hoseini N. Chin J Catal, 2012, 33: 706
27 Tavakoli-Hoseini N, Davoodnia A. Asian J Chem, 2010, 22: 7197
28 Heravi M M, Saeedi M, Karimi N, Zakeri M, Beheshtiha Y S, Davoodnia A. Synth Commun, 2010, 40: 523
29 Seifi N, Zahedi-Niaki M H, Reza Barzegari M, Davoodnia A, Zhiani R, Kaju A A. J Mol Catal A, 2006, 260: 77
30 Davoodnia A. Asian J Chem, 2010, 22: 1595
31 Norouzi H, Davoodnia A, Bakavoli M, Zeinali-Dastmalbaf M, Tavakoli-Hoseini N, Ebrahimi M. Bull Korean Chem Soc, 2011, 32: 2311
32 Zeinali-Dastmalbaf M, Davoodnia A, Heravi M M, Tava-koli-Hoseini N, Khojastehnezhad A, Zamani H A. Bull Korean Chem Soc, 2011, 32: 656
33 Tavakoli-Hoseini N, Davoodnia A. Chin J Chem, 2011, 29: 203
34 Khojastehnezhad A, Davoodnia A, Bakavoli M, Tava-koli-Hoseini N, Zeinali-Dastmalbaf M. Chin J Chem, 2011, 29: 297
35 Davoodnia A. Synth React Inorg Met-Org Nano-Met Chem, 2012, 42: 1022
36 Mohammadzadeh-Dehsorkh N, Davoodnia A, Tava-koli-Hoseini N, Moghaddas M. Synth React Inorg Met-Org Nano-Met Chem, 2011, 41: 1135
37 Davoodnia A. Bull Korean Chem Soc, 2011, 32: 4286
38 Fournier M. Inorg Synth, 1990, 27: 80
39 Song G, Wang B, Luo H, Yang L. Catal Commun, 2007, 8: 673

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