Copyright (c) 2018 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Efficient and Clean Synthesis of 1,8-Dioxooctahydroxanthenes in Aqueous Medium
Corresponding Author(s) : Santosh B. Pore
Asian Journal of Chemistry,
Vol. 30 No. 12 (2018): Vol 30 Issue 12
Abstract
In this work, an efficient synthesis of 1,8-dioxooctahydroxanthenes in aqueous medium is reported. The reaction was catalyzed by aqueous extract of plant material (pericarp of Sapindus trifoliatus fruit), which makes this protocol 'green' and eco-friendly. Differently substituted aromatic aldehydes underwent condensation with dimedone resulting in the formation of only the desired product in good to excellent yield. This reaction provides an alternative route to useful organic substances, employing simple reaction conditions, without organic solvents and hazardous chemical catalysts.
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References
K.R. Mohan Naidu, B.S. Krishna, M.A. Kumar, P. Arulselvan, S.I. Khalivulla and O. Lasekan, Molecules, 17, 7543 (2012); https://doi.org/10.3390/molecules17067543.
M. Kaya, E. Demir and H. Bekci, J. Enzyme Inhib. Med. Chem., 28, 885 (2013); https://doi.org/10.3109/14756366.2012.692087.
A.G. Banerjee, L.P. Kothapalli, P.A. Sharma, A.B. Thomas, R.K. Nanda. S.K. Shrivastava and V.V. Khatanglekar, Arab. J. Chem., 9(Suppl. 1), S480 (2016); https://doi.org/10.1016/j.arabjc.2011.06.001.
S.T.G. Buck, F. Bettanin, E. Orestes, P. Homem-de-Mello, H. Imasato, R.B. Viana, J.R. Perussi and A.B.F. da Silva, J. Chemistry, Article ID 7365263 (2017); https://doi.org/10.1155/2017/7365263.
G. Saint-Ruf, A. De and H.T. Hieu, Bull. Chim. Ther., 7, 83 (1972).
S. Hatakeyma, H. Numata and S. Takano, J. Chem. Soc., 1202 (1988); https://doi.org/10.1039/C39880001202.
G. Song, B. Wang, H. Luo and L. Yang, Catal. Commun., 8, 673 (2007); https://doi.org/10.1016/j.catcom.2005.12.018.
W.S. Johnson, Angew. Chem. Int. Ed. Engl., 15, 9 (1976); https://doi.org/10.1002/anie.197600091.
R.B. Herbert, Nat. Prod. Rep., 8, 185 (1991); https://doi.org/10.1039/np9910800185.
J. Kinjo, H. Uemura, T. Nohara, M. Yamashita, N. Marubayashi and K. Yoshihira, Tetrahedron Lett., 36, 5599 (1995); https://doi.org/10.1016/00404-0399(50)1071O-.
S.M. Menchen, S.C. Benson, J.Y.L. Lam, W. Zhen, B. Rosenblum, D. Sun, S.H. Khan and M. Taing, Sulfonated Diarylrhodamine Dyes, US Patent (2003).
El Sayed H. El Ashry, L.F. Awad, El Sayed I. Ibrahim and O.K. Bdeewy, ARKIVOC, 178 (2006); https://doi.org/10.3998/ark.5550190.0007.220.
C.G. Knight and T. Stephens, Biochem. J., 258, 683 (1989); https://doi.org/10.1042/bj2580683.
S. Miskoski, A.T. Soltermann, P.G. Molina, G. Gunther, A.L. Zanocco
and N.A. Garcia, Photochem. Photobiol., 81, 325 (2005); https://doi.org/10.1562/2004-10-27-RA-352.1.
Z.E. Selvanayagam, S.G. Gnanavendhan, K. Balakrishna, R.B. Rao, J. Sivaraman, K. Subramanian, R. Puri and R.K. Puri, J. Nat. Prod., 59, 664 (1996); https://doi.org/10.1021/np960355p.
T. Suzuki, M. Moriya, T. Sakamoto, T. Suga, H. Kishino, H. Takahashi, M. Ishikawa, K. Nagai, Y. Imai, E. Sekino, M. Ito, H. Iwaasa, A. Ishihara, S. Tokita, A. Kanatani, N. Sato and T. Fukami, Bioorg. Med. Chem. Lett., 19, 3072 (2009); https://doi.org/10.1016/j.bmcl.2009.04.016.
S. Omura, Y. Iwai, K. Hinotozawa, Y. Takahashi, J. Kato, A. Nakagawa, A. Hirano, H. Shimizu and K. Haneda, J. Antibiot. (Tokyo), 35, 645 (1982); https://doi.org/10.7164/antibiotics.35.645.
N. Mulakayala, P.V.N.S. Murthy, D. Rambabu, M. Aeluri, R. Adepu, G.R. Krishna, C.M. Reddy, K.R.S. Prasad, M. Chaitanya, C.S. Kumar, M.V. Basaveswara Rao and M. Pal, Bioorg. Med. Chem. Lett., 22, 2186 (2012); https://doi.org/10.1016/j.bmcl.2012.01.126.
I. Mohammadpoor-Baltork, M. Moghadam, S. Tangestaninejad, V. Mirkhani and H.R. Tavakoli, Chin. Chem. Lett., 22, 9 (2011); https://doi.org/10.1016/j.cclet.2010.09.003.
A. Khazaei, A.R. Moosavi-Zare, Z. Mohammadi, V. Khakyzadeh, A. Zare and G. Darvishi, RSC Adv., 3, 1323 (2013); https://doi.org/10.1039/C2RA22595F.
M.A. Ghasemzadeh, J. Safaei-Ghomi and S. Zahedi, J. Serb. Chem. Soc., 78, 769 (2013); https://doi.org/10.2298/JSC120624156G.
H. Khabazzadeh, I. Sheikhshoaie and N. Sotudeh, J. Sci. I. R. Iran, 24, 123 (2013).
A. Bamoniri, B.F. Mirjalili and S. Nazemian, Curr. Chem. Lett., 2, 27 (2013); https://doi.org/10.5267/j.ccl.2012.12.002.
S. Sadat and F. Hatamjafari, Orient. J. Chem., 31, 1191 (2015); https://doi.org/10.13005/ojc/310275.
M. Dabiri, S.C. Azimi and A. Bazgir, Chem. Pap., 62, 522 (2008); https://doi.org/10.2478/s11696-008-0050-y.
M.M. Amini, Y. Fazaeli, Z. Yassaee, S. Feizi and A. Bazgir, The Open Catal. J., 2, 40 (2009); https://doi.org/10.2174/1876214X00902010040.
S. Pore, G. Rashinkar, K. Mote and R. Salunkhe, Chem. Biodiv., 7, 1796 (2010); https://doi.org/10.1002/cbdv.200900272.
E. Mosaddegh, M.R. Islami and A. Hassankhani, Arab. J. Chem., 5, 77 (2012); https://doi.org/10.1016/j.arabjc.2010.07.027.
T. Jin, A. Wang, H. Ma, J. Zhang and T.-S. Li, Indian J. Chem., 45B, 470 (2006).