Skip to content
BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access August 11, 2008

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

Qi-Fang Wang and Chao-Guo Yan
From the journal Open Chemistry


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.

[1] A. Dömling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)<3168::AID-ANIE3168>3.0.CO;2-U10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-USearch in Google Scholar

[2] D. J. Ramon, Y. Miguel, Angew. Chem. Int. Ed. 44, 1602 (2005) in Google Scholar

[3] L. F. Tiets, Chem. Rev. 96, 115 (1996) in Google Scholar

[4] G. Balme, E. Bossharth, N. Monteiro, Eur. J. Org. Chem. 4101 (2003) 10.1002/ejoc.200300378Search in Google Scholar

[5] R. V. A. Orru, M. de Greef, Synthesis, 1471–1499 (2003) 10.1055/s-2003-40507Search in Google Scholar

[6] L. Weber, K. Illgen, M. Almstetter, Synlett., 366 (1999) 10.1055/s-1999-2612Search in Google Scholar

[7] L. Perreux, A. Loupy, Tetrahedron, 57, 9199 (2001) in Google Scholar

[8] S. Caddick, Tetrahedron, 51, 10403 (1995) in Google Scholar

[9] K. Tnaka, Solvent-free Organic Synthesis, Wiley-VCH, Weinheim, 2003 10.1002/3527601821Search in Google Scholar

[10] D. Barton, D. Ollis, Comprehensive Organic Chemistry, The synthesis & Reactions of Organic Compounds, Pergaman: New York, Vol. 4, p468 (1979) Search in Google Scholar

[11] A. R. Katritzky, C. M. Marson, Angew. Chem. Int. Edit. 23, 420 (1984) in Google Scholar

[12] E. C. Constable, R. Martínz-Máòez, A. M. W. Chargill Thompson, J. V. Walker, J. Chem. Soc. Dalton Trans. 1585 (1994) Search in Google Scholar

[13] I. Eryazici, C. N. Moorefield, S. Durmus, G. R. J. Newkome, Org. Chem. 71(3), 1009 (2006) in Google Scholar

[14] G. Jones, In Comprehensive Heterocyclic Chemistry; A. R. Katritzky, C. W. Rees, Eds.; Pergaman: New York, Vol.2, part 2A, p395 (1984) Search in Google Scholar

[15] A. Sausinš, D. G. Durburs, Heterocycles, 27, 291 (1988) in Google Scholar

[16] G. W. V. Cave, C. L. Raston, Chem. Commun. 2199 (2000) 10.1039/b007431oSearch in Google Scholar

[17] A. Kowalkowska, D. Sucholbiak, A. Jonczyk, Eur. J. Org. Chem. 925 (2005) 10.1002/ejoc.200400556Search in Google Scholar

[18] S. Tu, R. Jia, B. Jiang, J. Zhang, Y. Zhang, C. Yao, S. Ji, Tetrahedron, 63, 381 (2007) in Google Scholar

[19] S. Tu, T. Li, F. Shi, F. Fang, S. Zhu, X. Wei, Z. Zong, Chem. Lett. 34, 732 (2005) in Google Scholar

[20] S. Tu, B. Jiang, R. Jia, J. Zhang, Y. Zhang, Tetrahedron Lett. 48, 1369 (2007) in Google Scholar

[21] M. Adib, H. Tahermansouri, S. A. Koloogani, B. Mohammdi, H. R Bijanzadeh, Tetrahedron Lett. 47, 5957 (2006) in Google Scholar

[22] C. G. Yan, X. M. Cai, Q. F. Wang, T. Y. Wang, M. Zheng, Org. Biomol. Chem. 5, 945 (2007) in Google Scholar

[23] D. M. Perreault, L. A. Cabell, Bioorg. Med. Chem. 5(6), 1209 (1997) in Google Scholar

[24] V. Baliah, R. Jeyaraman, Indian. J. Chem. Sect. B. 15B(9), 798 (1997) Search in Google Scholar

[25] V. I. Vysotskii, M. N. Tilichenko, Khim. Geterotsikl. Soedin. (6), 1080 (1968) Search in Google Scholar

[26] V. I. Vysotskii, M. N. Tilichenko, Khim. Geterotsikl. Soedin. (11), 1542 (1970) Search in Google Scholar

[27] R. P. Thummel, Y. Jahng, J. Org. Chem. 50(14), 2407 (1985) in Google Scholar

[28] M. N. Tilichenko, I. A. Koroleva-Vasil’eva, T. I. Akimova, Zh. Org. Khim. 22(9), 1920 (1986) Search in Google Scholar

[29] N. Nakamichi, Y. Kawashita, M. Hayashi, M. Org. Lett. 4, 3955 (2002) in Google Scholar

[30] G. Sabitha, G. S. K. Reddy, C. S. Reddy, N. Fatima, J. S. Yadav, Synthesis, 1267 (2003) Search in Google Scholar

[31] N. Natsuki, K. Yuka, H. Masahiko, Synthesis, 1015 (2004) Search in Google Scholar

[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) 10.1039/a907077jSearch in Google Scholar

[33] M. Rahman, B. S. Jeong, D. H. Kim, J. K. Park, E. S. Lee, Y. Jahng, Tetrahedron, 63, 2426 (2007) in Google Scholar

[34] A. Arnold, M. Markert, R. Mahrwald, Synthesis, 1099 (2006) Search in Google Scholar

[35] C. Y. Huang, L. A. Cabell, E. V. Anslyn, Tetrahedron Lett. 51, 7411 (1990) in Google Scholar

[36] U. Westerwelle, A. Esser, N. Risch, Chem. Ber. 124, 571 (1991) in Google Scholar

Published Online: 2008-8-11
Published in Print: 2008-9-1

© 2008 Versita Warsaw

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Scroll Up Arrow