Abstract
Saccharose was applied as a green and natural catalyst for the one-pot, three-component condensation between aromatic aldehydes, malononitrile, and resorcinol, or 4-hydroxycoumarine to afford the corresponding pyran-annulated heterocyclic systems. This green methodology offers several advantages such as the use of a non-hazardous catalyst, easy access, clean work-up, excellent yields, short reaction time, and environmentally mild conditions. In addition, 1,8-dioxodecahydroacridine and 2-substituted benzimidazole derivatives have been synthesized from commercially available starting materials, arylaldehydes, dimedone, amines, or ammonium acetate and o-phenylenediamine using the mentioned catalyst.
Graphical abstract
Similar content being viewed by others
Explore related subjects
Discover the latest articles, news and stories from top researchers in related subjects.References
F.M. Dean, Naturally occurring oxygen ring compounds (Butterworths, London, 1963)
L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28, 517 (1993)
G.M. Cingolani, F. Gualtteri, M. Pigin, J. Med. Chem. 12, 531 (1969)
J.Y.C. Wu, W.F. Fong, J.X. Zhang, C.H. Leung, H.L. Kwong, M.S. Yang, D. Li, H.Y. Cheung, Eur. J. Pharmacol. 473, 9 (2003)
P.G. Baraldi, S. Manfredini, D. Simoni, M. Aghazadeh Tabrizi, J. Balzarini, E. De Clercq, J. Med. Chem. 35, 1877 (1992)
Y. Kashman, K.R. Gustafson, R.W. Fuller, J.H. Cardellina II, J.B. McMahon, M.J. Currens, R.W. Buckheit Jr, S.H. Hughes, G.M. Cragg, M.R. Boyd, J. Med. Chem. 35, 2735 (1992)
L.L. Andreani, E. Lapi, Boll. Chim. Farm. 99, 583 (1960)
G.P. Ellis, In Chromenes, Chromanones and Chromones; A. Weissberger, Taylor, E. C. Eds.; John Wiley & Sons: New York (1977)
D. Armesto, W.M. Horspool, N. Martin, A. Ramos, C. Seoane, J. Org. Chem. 54, 3069 (1989)
F.F. Abdel-Latif, Indian J. Chem., Sect B, 29B, 664 (1990)
Y. Peng, G. Song, Catal. Commun. 8, 111 (2007)
T.S. Jin, L.B. Liu, Y. Zhao, T.S. Li, Synth. Commun. 35, 1859 (2005)
N. Seshu Babu, N. Pasha, K.T. Venkateswara Rao, P.S. Sai Prasad, N. Lingaiah, Tetrahedron Lett. 49, 2730 (2008)
M.M. Heravi, Y.S. Beheshtiha, Z. Pirnia, S. Sadjadi, M. Adibi, Synth. Commun. 39, 3663 (2009)
T.S. Jin, J.C. Xiao, S.J. Wang, T.S. Li, Ultrason. Sonochem. 11, 393 (2004)
N. Martin, C. Seoane, J.L. Soto, Tetrahedron 44, 5861 (1988)
V.D. Dyachenko, Russ. J. Gen. Chem. 76, 282 (2006)
K. Gong, H.L. Wang, J. Luo, Z.L. Liu, J. Heterocycl. Chem. 46, 1145 (2009)
S. Gao, C.H. Tsai, C. Tseng, C.F. Yao, Tetrahedron 64, 9143 (2008)
S. Banerjee, A. Horn, H. Khatri, G. Sereda, Tetrahedron Lett. 52, 1878 (2011)
D.S. Raghuvanshi, K.N. Singh, Arkivoc x, 305 (2010)
S. Makarem, A.A. Mohammadi, A.R. Fakhari, Tetrahedron Lett. 49, 7194 (2008)
S.A. Gamaga, J.A. Spicer, G.J. Atwell, G.J. Finlay, B.C. Baguley, W.A. Denny, J. Med. Chem. 42, 2383 (1999)
I. Antonini, P. Polucci, L.R. Kelland, E. Menta, N. Pescalli, S. Martelli, J. Med. Chem. 42, 2535 (1999)
Y. Mikata, M. Yokoyama, K. Mogami, M. Kato, I. Okura, M. Chikira, S. Yano, Inorganica Chim. Acta 279, 51 (1998)
S. Gallo, S. Atifi, A. Mohamoud, C. Santelli-Rouvier, K. Wolfárt, J. Molnar, J. Barbe, Eur. J. Med. Chem. 38, 19 (2003)
L. Ngadi, A.M. Galy, J.P. Galy, J. Barbe, A. Crémieux, J. Chevalier, D. Sharples, Eur. J. Med. Chem. 25, 67 (1990)
M. Wainwright, J. Antimicrob. Chemother. 47, 1 (2001)
M. Kidwai, D. Bhatnagar, Tetrahedron Lett. 51, 2700 (2010)
W. Shen, L.M. Wang, H. Tian, J. Tang, J.J. Yu, J. Fluor Chem. 130, 522 (2009)
D.Q. Shi, S.N. Ni, F. Yang, J.W. Shi, G.L. Dou, X.-Y. Li, X.-S. Wang, J. Heterocycl Chem. 45, 653 (2008)
M. Dabiri, M. Baghbanzadeh, E. Arzroomchilar, Catal. Commun. 9, 939 (2008)
K. Venkatesan, S.S. Pujari, K.V. Srinivasan, Synth. Commun. 39, 228 (2009)
B. Das, P. Thirupathi, I. Mahender, V.S. Reddy, Y.K. Rao, J. Mol. Catal. A Chem. 247, 233 (2006)
A. Davoodnia, A. Khojastehnezhad, N. Tavakoli-Hoseini, Bull. Korean Chem. Soc. 32, 2243 (2011)
F. Rashedian, D. Saberib, K. Niknam, J. Chin. Chem. Soc. 57, 998 (2010)
T.S. Jin, J.S. Zhang, T.T. Guo, A.Q. Wang, T.S. Li, Synthesis 12, 2001 (2004)
G. Mohammadi Ziarani, A. Badiei, M. Hassanzadeh, S. Mousavi, Arab. J. Chem. 2011, doi:10.1016/j.arabjc.2011.01.037
N. Hazeri, A. Masoumnia, M.T. Mghsoodlou, S. Salahi, M. Kangani, S. Kianpour, S. Kiaee, J. Abonajmi. Res. Chem. Intermed. doi:10.1007/s11164-013-1516-2
W.A. Denny, G.W. Rewcastle, B.C. Baguley, J. Med. Chem. 33, 814 (1990)
T. Fonseca, B. Gigante, T.L. Gilchrist, Tetrahedron 57, 1793 (2001)
Y. Kohara, K. Kubo, E. Imamiya, T. Wada, Y. Inada, T. Naka, J. Med. Chem. 39, 5228 (1996)
A.R. Porcari, R.V. Devivar, L.S. Kucera, J.C. Drach, L.B. Townsend, J. Med. Chem. 41, 1252 (1998)
H. Zarrinmayeh, D.M. Zimmerman, B.E. Cantrell, D.A. Schober, R.F. Bruns, S.L. Gackenheimer, P.L. Ornstein, P.A. Hipskind, T.C. Britton, D.R. Gehlert, Bioorg. Med. Chem. Lett. 9, 647 (1999)
N. Hazeri, M.T. Maghsoodlou, F. Mir, M. Kangani, H. Saravani, E. Molashahi, Chin. J. Catal. 35, 391 (2014)
N. Hazeri, M.T. Maghsoodlou, M.R. Mousavi, J. Aboonajmi, M. Safarzaei, Res. Chem. Intermed. (2013). doi:10.1007/s11164-013-1179-z
M.R. Mousavi, N. Hazeri, M.T. Maghsoodlou, S. Salahi, S.M. Habibi-Khorassani, Chin. Chem. Lett. 24, 411 (2013)
N. Hazeri, S.S. Sajadikhah, M.T. Maghsoodlou, M. Norouzi, M. Moin, S. Mohamadian-Souri, J. Chem. Res. 550 (2013)
M. Kidwai, S. Saxena, Synth. Commun. 36, 2737 (2006)
J.M. Khurana, S. Kumar, Tetrahedron Lett. 50, 4125 (2009)
D.-Q. Shi, J. Wang, Q.-Y. Zhuang, X.-S. Wang, Chin. J. Org. Chem. 26, 643 (2006)
M.M. Heravi, B.A. Jani, F. Derikvand, F.F. Bamoharram, H.A. Oskooie, Catal. Commun. 10, 272 (2008)
R.M. Shaker, Pharmazie 51, 148 (1996)
S. Abdolmohammadi, S. Balalaie, Tetrahedron Lett. 48, 3299 (2007)
H. Mehrabi, H. Abusaidi, J. Iran. Chem. Soc. 7, 890 (2010)
F.K. Behbahani, P. Ziaei, Chem. Heterocycl. Compd. 48, 1011 (2012)
H.M. Bachhav, S.B. Bhagat, V.N. Telvekar, Tetrahedron Lett. 52, 5697 (2011)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Maghsoodlou, M.T., Hazeri, N., Lashkari, M. et al. Saccharose as a new, natural, and highly efficient catalyst for the one-pot synthesis of 4,5-dihydropyrano[3,2-c]chromenes, 2-amino-3-cyano-4H-chromenes, 1,8-dioxodecahydroacridine, and 2-substituted benzimidazole derivatives. Res Chem Intermed 41, 6985–6997 (2015). https://doi.org/10.1007/s11164-014-1793-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-014-1793-4