Efficient synthesis of diarylidene octahydroacridines by one-pot multi-component tandem reactions

• Authors: Qi-Fang Wang , Chao-Guo Yan
• Languages of publication: EN

Abstracts

EN

A one-pot multi-component reaction is developed for the efficient synthesis of 4,5-dibenzylidene octahydroacridines in high yields. The reaction is performed by the tandem reaction of three molar equivalent aromatic aldehydes with two molar equivalent 4-alkylcyclohexanone in the system of NH4OAc/HOAc under microwave irradiation. [...]

Keywords

EN

Pyridine; Octahydroacridine; One-pot reaction; Multi-component reaction; Microwave irradiation

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2008
• Volume: 6
• Issue: 3
• Pages: 404-409

Dates

published

1 - 9 - 2008

online

11 - 8 - 2008

Contributors

author

Qi-Fang Wang

• College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, 225002, China

author

Chao-Guo Yan

• College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, 225002, China

References

• [1] A. Dömling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000) http://dx.doi.org/10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U[Crossref]
• [2] D. J. Ramon, Y. Miguel, Angew. Chem. Int. Ed. 44, 1602 (2005) http://dx.doi.org/10.1002/anie.200460548[Crossref]
• [3] L. F. Tiets, Chem. Rev. 96, 115 (1996) http://dx.doi.org/10.1021/cr950027e[Crossref]
• [4] G. Balme, E. Bossharth, N. Monteiro, Eur. J. Org. Chem. 4101 (2003) [Crossref]
• [5] R. V. A. Orru, M. de Greef, Synthesis, 1471–1499 (2003)
• [6] L. Weber, K. Illgen, M. Almstetter, Synlett., 366 (1999) [Crossref]
• [7] L. Perreux, A. Loupy, Tetrahedron, 57, 9199 (2001) http://dx.doi.org/10.1016/S0040-4020(01)00905-X[Crossref]
• [8] S. Caddick, Tetrahedron, 51, 10403 (1995) http://dx.doi.org/10.1016/0040-4020(95)00662-R[Crossref]
• [9] K. Tnaka, Solvent-free Organic Synthesis, Wiley-VCH, Weinheim, 2003
• [10] D. Barton, D. Ollis, Comprehensive Organic Chemistry, The synthesis & Reactions of Organic Compounds, Pergaman: New York, Vol. 4, p468 (1979)
• [11] A. R. Katritzky, C. M. Marson, Angew. Chem. Int. Edit. 23, 420 (1984) http://dx.doi.org/10.1002/anie.198404201[Crossref]
• [12] E. C. Constable, R. Martínz-Máòez, A. M. W. Chargill Thompson, J. V. Walker, J. Chem. Soc. Dalton Trans. 1585 (1994) [Crossref]
• [13] I. Eryazici, C. N. Moorefield, S. Durmus, G. R. J. Newkome, Org. Chem. 71(3), 1009 (2006) http://dx.doi.org/10.1021/jo052036l[Crossref]
• [14] G. Jones, In Comprehensive Heterocyclic Chemistry; A. R. Katritzky, C. W. Rees, Eds.; Pergaman: New York, Vol.2, part 2A, p395 (1984)
• [15] A. Sausinš, D. G. Durburs, Heterocycles, 27, 291 (1988) http://dx.doi.org/10.3987/REV-87-371[Crossref]
• [16] G. W. V. Cave, C. L. Raston, Chem. Commun. 2199 (2000) [Crossref]
• [17] A. Kowalkowska, D. Sucholbiak, A. Jonczyk, Eur. J. Org. Chem. 925 (2005) [Crossref]
• [18] S. Tu, R. Jia, B. Jiang, J. Zhang, Y. Zhang, C. Yao, S. Ji, Tetrahedron, 63, 381 (2007) http://dx.doi.org/10.1016/j.tet.2006.10.069[Crossref]
• [19] S. Tu, T. Li, F. Shi, F. Fang, S. Zhu, X. Wei, Z. Zong, Chem. Lett. 34, 732 (2005) http://dx.doi.org/10.1246/cl.2005.732[Crossref]
• [20] S. Tu, B. Jiang, R. Jia, J. Zhang, Y. Zhang, Tetrahedron Lett. 48, 1369 (2007) http://dx.doi.org/10.1016/j.tetlet.2006.12.102[Crossref]
• [21] M. Adib, H. Tahermansouri, S. A. Koloogani, B. Mohammdi, H. R Bijanzadeh, Tetrahedron Lett. 47, 5957 (2006) http://dx.doi.org/10.1016/j.tetlet.2006.01.162[Crossref]
• [22] C. G. Yan, X. M. Cai, Q. F. Wang, T. Y. Wang, M. Zheng, Org. Biomol. Chem. 5, 945 (2007) http://dx.doi.org/10.1039/b617256c[Crossref]
• [23] D. M. Perreault, L. A. Cabell, Bioorg. Med. Chem. 5(6), 1209 (1997) http://dx.doi.org/10.1016/S0968-0896(97)00051-5[Crossref]
• [24] V. Baliah, R. Jeyaraman, Indian. J. Chem. Sect. B. 15B(9), 798 (1997)
• [25] V. I. Vysotskii, M. N. Tilichenko, Khim. Geterotsikl. Soedin. (6), 1080 (1968)
• [26] V. I. Vysotskii, M. N. Tilichenko, Khim. Geterotsikl. Soedin. (11), 1542 (1970)
• [27] R. P. Thummel, Y. Jahng, J. Org. Chem. 50(14), 2407 (1985) http://dx.doi.org/10.1021/jo00214a001[Crossref]
• [28] M. N. Tilichenko, I. A. Koroleva-Vasil’eva, T. I. Akimova, Zh. Org. Khim. 22(9), 1920 (1986)
• [29] N. Nakamichi, Y. Kawashita, M. Hayashi, M. Org. Lett. 4, 3955 (2002) http://dx.doi.org/10.1021/ol0268135[Crossref]
• [30] G. Sabitha, G. S. K. Reddy, C. S. Reddy, N. Fatima, J. S. Yadav, Synthesis, 1267 (2003)
• [31] N. Natsuki, K. Yuka, H. Masahiko, Synthesis, 1015 (2004)
• [32] M. G. B. Drew, P. B. Ivson, M. J. Hudson, J. O. Liljenzin, L. Spjuth, P. Y. Cordier, A. Enarssson, C. Hill, C. Madic, J. Chem. Soc., Dalton Trans. 821 (2000) [Crossref]
• [33] M. Rahman, B. S. Jeong, D. H. Kim, J. K. Park, E. S. Lee, Y. Jahng, Tetrahedron, 63, 2426 (2007) http://dx.doi.org/10.1016/j.tet.2007.01.020[Crossref]
• [34] A. Arnold, M. Markert, R. Mahrwald, Synthesis, 1099 (2006)
• [35] C. Y. Huang, L. A. Cabell, E. V. Anslyn, Tetrahedron Lett. 51, 7411 (1990) http://dx.doi.org/10.1016/S0040-4039(00)88502-0[Crossref]
• [36] U. Westerwelle, A. Esser, N. Risch, Chem. Ber. 124, 571 (1991) http://dx.doi.org/10.1002/cber.19911240324[Crossref]

Identifiers

DOI

10.2478/s11532-008-0027-2