Abstract
N-Acyl-1,3-diaryl-2-azaphenalene derivatives have been synthesized by one-pot condensation reaction of aromatic aldehydes, 2,7-naphthalenediol, carboxylic acids, and aqueous ammonia (25 %). Different aromatic aldehydes and carboxylic acids have been used in the reaction and the products were always obtained in good to high yields. The method is simple, solvent free, and involves a short reaction time. These relatively rapid reactions possibly proceed via a Betti reaction mechanism.
Graphical Abstract
Similar content being viewed by others
References
A. Dömling, Chem. Rev. 106, 17 (2006)
C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem. 4957 (2004)
H. Bienayme, C. Hulme, G. Oddon, P. Schmitt, Chem. Eur. J. 6, 3321 (2000)
A. Ulaczyk-Lesanko, D.G. Hall, Curr. Opin. Chem. Biol. 9, 266 (2005)
L. Weber, Curr. Med. Chem. 9, 2085 (2002)
C. Hulme, V. Gore, Curr. Med. Chem. 10, 51 (2003)
A. Strecker, Ann. Chem. Pharm. 75, 27 (1850)
A.K. Bose, S. Pednekar, S.N. Ganguly, G. Chakraborty, M.S. Manhas, Tetrahedron Lett. 45, 8351 (2004)
T.A. Keating, R.W. Armstrong, J. Am. Chem. Soc. 117, 7842 (1995)
K. Kobayashi, T. Matoba, S. Irisawa, T. Matsumoto, O. Morikawa, H. Konishi, Chem. Lett. 27, 551 (1998)
G. Zhao, T. Jiang, H. Gao, B. Han, J. Huang, D. Sun, Green Chem. 6, 75 (2004)
D.J. Ramon, M. Yus, Angew. Chem. Int. Ed. 44, 1602 (2005)
M. Betti, Org. Synth. Coll. 1, 381 (1941)
I. Szatmári, F. Fülöp, Curr. Org. Synth. 1, 155 (2004)
I. Szatmári, T.A. Martinek, L. Lázár, F. Fülöp, Tetrahedron 59, 2877 (2003)
I. Szatmári, T.A. Martinek, L. Lázár, A. Koch, E. Kleinpeter, K. Neuvonen, F. Fülöp, J. Org. Chem. 69, 3645 (2004)
I. Szatmári, T.A. Martinek, L. Lázár, F. Fülöp, Eur. J. Org. Chem. 2231 (2004)
I. Szatmári, F. Fülöp, Tetrahedron 69, 1255 (2013)
C. Cimarelli, A. Mazzanti, G. Palmieri, E. Volpini, J. Org. Chem. 66, 4759 (2001)
C. Rondot, J. Zhu, Org. Lett. 7, 1641 (2005)
Z. Turgut, E. Pelit, A. Köycü, Molecules 12, 345 (2007)
A.Y. Shen, C.T. Tsai, C.L. Chen, Eur. J. Med. Chem. 34, 877 (1999)
I. Szatmari, A. Hetenyi, L. Lazar, F. Fulop, J. Heterocycl. Chem. 41, 367 (2004)
R.C. Haddon, Nature 256, 394 (1975)
M.E. Itkis, X. Chi, A.W. Cordes, R.C. Haddon, Science 296, 1443 (2002)
S. Shimizu, H. Zhu, N. Kobayashi, Chemistry 16, 11151 (2010)
J.L. Hodgson, M. Namazian, S.E. Bottle, M.L. Coote, J. Phys. Chem. A 111, 13595 (2007)
D. Daloze, J.-C. Braekman, J. Pasteels, Chemoecology 5, 173 (1994)
N. Foroughifar, A. Mobinikhaledi, H. Moghanian, Synth. Commun. 40, 1812 (2010)
N. Foroughifar, A. Mobinikhaledi, H. Moghanian, Chem. Lett. 39, 180 (2010)
A. Mobinikhaledi, H. Moghanian, M. Deinavizadeh, Comptes rendus Chimie 16, 1035 (2013)
H. Moghanian, M. Shabanian, H. Jafari, Comptes rendus Chimie 15, 346 (2012)
H. Moghanian, S. Ebrahimi, J. Saudi Chem. Soc. 18, 165 (2014)
A. Mobinikhaledi, H. Moghanian, F. Sasani, Synth. React. Metal-Org. Nano-Met. Chem. 41, 262 (2011)
A.A. Khosropour, M.M. Khodaei, H. Moghannian, Synlett 955 (2005)
H. Jafari, H. Moghanian, Lett. Org. Chem. 9, 273 (2012)
N. Foroughifar, A. Mobinikhaledi, H. Moghanian, Synth. Commun. 39, 3668 (2009)
M. Lubben, B.L. Feringa, J. Org. Chem. 59, 2227 (1994)
Acknowledgments
We gratefully acknowledge financial support from the Research Council of Arak University.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Mobinikhaledi, A., Foroughifar, N., Moghanian, H. et al. Convenient one-pot synthesis of N-acyl-1,3-diaryl-2-azaphenalene derivatives via solvent-free five-component condensation reactions. Res Chem Intermed 41, 6523–6532 (2015). https://doi.org/10.1007/s11164-014-1758-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-014-1758-7