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http://dx.doi.org/10.5012/bkcs.2009.30.11.2555

Ammonium Acetate: An Efficient Reagent for the One-pot Synthesis of 5-Aryl-7,8,13,14-tetrahydrodibenzo[a,i] phenanthridines, 2,4-Diaryl-6,7-benzo-3-azabicyclo[3.3.1]nonan-9-ones and α,α'-Bis(substituted benzylidene)cycloalkanones  

Karthikeyan, Natesan Sundaramurthy (Chemistry Division, School of Science and Humanities, VIT University)
Sathiyanarayanan, Kulathu Iyer (Chemistry Division, School of Science and Humanities, VIT University)
Aravindan, Paduthapillai Gopal (Physics Division, School of Science and Humanities, VIT University)
Publication Information
Abstract
The condensation of cyclic ketone with aromatic aldehydes in the presence of ammonium acetate under ethanol media affords the corresponding 5-aryl-7,8,13,14-tetrahydrodibenzo[a,i]phenanthridine with excellent yield. This mild and efficient procedure with high yield is also applied to the synthesis of 2,4-diaryl-6,7-benzo-3-azabicyclo- [3.3.1]nonan-9-ones and ${\alpha},{\alpha}{$’-bis(substituted benzylidene)cycloalkanones.
Keywords
Cyclic ketone; Aromatic aldehyde; Ammonium acetate; Mannich reaction; Cross aldol condensation;
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1 Gug, F.; Bach, S.; Blondel, M.; Vierfond, J. M.; Martin, A. S.; Galons, H. Tetrahedron 2004, 60, 4705   DOI   ScienceOn
2 Banwell, M. G.; Lupton, D. W.; Ma, X. H.; Renner, J.; Sydnes, M. O. Org. Lett. 2004, 6, 2741   DOI   ScienceOn
3 Hilt, G.; Hess, W.; Schmidt, F. Eur. J. Org. Chem. 2005, 2526
4 Liepa, A. J.; Nearn, R. N.; Wright, D. M. J. Aust. J. Chem. 2004, 7, 473
5 Costi, R.; Santo, R. D.; Artico, M.; Massa, S.; Rangno, R.; Loddo, R.; Colla, M. L.; Tramonontano, E.; Colla, P. L.; Pani, A. Bioorg. Med. Chem. 2004, 12, 199   DOI   ScienceOn
6 Weber, W. M.; Hunsaker, L. A.; Abcouwer, S. F.; Deck, L. M.; Jagt, D. L. V. Bioorg. Med. Chem. 2005, 13, 3811   DOI   ScienceOn
7 Karthikeyan, N. S.; Sathiyanarayanan, K.; Aravindan, P. G.; Giridharan, P. Med. Chem. Res. – Communnicated
8 Zhang, L.; Wang, S.; Sheng, E.; Zhou, S. Green Chem. 2005, 7, 683   DOI   ScienceOn
9 Bhagat, S.; Sharma, R.; Chakraborti, A. K. J. Mol. Catalysis A: Chem. 2006, 260, 235   DOI   ScienceOn
10 Herrera, A.; Alvarez, R. M.; Chioua, M.; Chatt, R.; Chioua, R.; Sanchez, A.; Almy, J. Tetrahedron 2006, 62, 2799   DOI   ScienceOn
11 Gonzalez, B.; Herrera, A.; Illescab, B.; Martin, N.; Martinez, R.; Moreno, F.; Sanchez, L.; Sanchez, A. J. Org. Chem. 1998, 63, 6807   DOI   ScienceOn
12 Sathiyanarayanan, K.; Karthikeyan, N. S.; Aravindan, P. G.; Shanthi, S.; Rathore, R. S.; Lee, C. W. J. Heterocycl. Chem. – Accepted (article in Press – DoI: 10.1002/jhet.191)   DOI
13 Mamalis, P.; Petrow, V. J. Chem. Soc. 1950, 703   DOI
14 Noller, C. R.; Baliah, V. J. Am. Chem. Soc. 1948, 70, 3853   DOI
15 Borst, P. IUBMB Life 2005, 57, 745   DOI   ScienceOn
16 Denny, W. A. Curr. Med. Chem. 2002, 9, 1655
17 Buu-Hui, N. P.; Jaquignon, P.; Long, C. T. J. Chem. Soc. 1957, 505   DOI
18 Kock, I.; Clement, B. Synthesis 2005, 7, 1052
19 Huitric, A. C.; Kumler, W. D. J. Am. Chem. Soc. 1956, 78, 614   DOI
20 Rovnyak, G.; Shu, V.; Schwartz, J. J. Heterocycl. Chem. 1981, 18, 327   DOI
21 Irie, K.; Watanabe. Bull. Chem. Soc. Jpn. 1980, 53, 1366   DOI   ScienceOn
22 Nakano, T.; Migita, T. Chem. Lett. 1993, 2157
23 Zeheng, M.; Wang, L.; Shao, J.; Zhong, Q. Synth. Commun. 1997, 27, 351   DOI   ScienceOn
24 Zheng, X.; Zhang, Y. Synth. Commun. 2003, 33, 161   DOI   ScienceOn
25 Li, J. T.; Yang, W. Z.; Chen, G. F.; Li, T. S. Synth. Commun. 2003, 33, 2619   DOI   ScienceOn
26 Abaee, M. S.; Mojtahedi, M. M.; Zahedi, M. M. Synthesis 2005, 2317
27 Rathore, R. S.; Karthikeyan, N. S.; Sathiyanarayanan, K.; Aravindan, P. G. J. Mol. Struct. – Aceepted (article in Press – DoI: 10.1016/j.molstruc.2009.10.007)   DOI   ScienceOn