Abstract
A new method has been proposed for the green and efficient synthesis of xanthenediones and their corresponding open-chain analogs aryl-methylene bis(3-hydroxy-5,5’-dimethyl-2-cyclohexene-1-ones) using natural acid, Lemon juice, as the catalyst. This method involves the use of lemon juice as a surfactant-type bronsted acid, which makes it non-polluting and produces a high-purity product with excellent yield. Additionally, the work-up procedure is clean and straightforward. Dimedone and aldehydes are the starting materials for this process.
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L.A. Thompson, Curr. Opin. Chem. Biol. 4, 324 (2000)
A. Nefzi, J.M. Ostresh, R.A. Houghten, Chem. Rev. 97, 449 (1997)
N. Mizuno, M, Misono. Chem. Rev. 98, 199 (1998)
J.P. Poupelin, G. Saint-Rut, O. Fussard-Blanpin, G. Narcisse, G. Uchida-Ernouf, R. Lakroix, Eur. J. Med. Chem. 13, 67 (1978)
M.A. Bhat, A.M. Naglah, S. Akber Ansari, H.M. Al-Tuwajiria, A. Al-Dhfyan, Molecules 26(12), 3667 (2021)
K. Chibale, M. Visser, D.V. Schalkwyk, P.J. Smith, A. Saravanamuthu, A.H. Fairlamb, Tetrahedron 59, 2289 (2003)
A. Banerjee, A.K. Mukherjee, Stain Technol. 56, 83 (1981)
C.G. Knight, T. Stephens, Biochem. J. 258, 683 (1989)
M. Farzaneh, M. Feilizadeh, Chem. Methodol. 4, 647 (2020)
X. Fan, X. Hu, X. Zhang, J. Wang, Can. J. Chem. 83, 16 (2005)
B. Karami, S. Nejati, K. Eskandari, Curr. Chem. Lett. 4(4), 169 (2015)
G.K. Verma, K. Raghuvanshi, R.K. Verma, P. Dwivedi, M.S. Singh, Tetrahedron 67, 3698 (2011)
X.S. Fan, Y.Z. Li, X.Y. Zhang, X.Y. Hu, J.J. Wang, Chin. J. Org. Chem. 25, 1482 (2005)
J.J. Ma, J.C. Li, R.X. Tang, X. Zhou, Q.H. Wu, C. Wang, M.M. Zhang, Q. Li, Chin. J. Org. Chem. 27, 640 (2007)
F. Darviche, S. Balalaie, F. Chadegani, P. Salehi, Synth. Commun. 37, 1059 (2007)
P.B. Pawar, S.D. Jadhav, M.B. Deshmukh, S.S. Patil, Indian J. Chem. 52B, 1185 (2014)
B. Das, P. Thirupathi, K.R. Reddy, B. Ravikanth, L. Nagarapu, Catal. Commun. 8, 535 (2007)
G.I. Shakibaei, P. Mirzaei, A. Bazgir, Appl. Catal. 325, 188 (2007)
B. Das, P. Thirupathi, I. Mahender, V.S. Reddy, Y.K. Rao, J. Mol. Catal. A Chem. 247, 233 (2006)
G. Song, B. Wang, H. Luo, L. Yang, Catal. Commun. 8, 673 (2007)
M. Seyyedhamzeh, P. Mirzaei, A. Bazgir, Dyes Pigm. 76, 836 (2008)
A. John, P.J.P. Yadav, S. Palaniappan, J. Mol. Catal. A Chem. 248, 121 (2006)
S. Kantevari, R. Bantu, L. Nagarapu, J. Mol. Catal. A Chem. 269, 53 (2007)
Z.H. Zhang, Y.H. Liu, Catal. Commun. 9, 1715 (2008)
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.B. Rao, M. Pal, Bioorg. Med. Chem. Lett. 22, 2186 (2012)
T.S. Jin, J.S. Zhang, A.Q. Wang, T.S. Li, Synth. Commun. 35, 2339 (2005)
H. Tavakol, M. Firouzi, Front. Chem. 10, 1015830 (2022)
T.S. Jin, J.S. Zhang, J.C. Xiao, A.Q. Wang, T.S. Li Synlett 5, 866 (2004)
S. Kantevari, R. Bantu, L. Nagarapu Arkivoc 16(6), 136 (2006)
D.Q. Shi, Q.Y. Zhuang, J. Chen, X.S. Wang, S.J. Tu, H.W. Hu, Chin. J. Org. Chem. 23, 694 (2003)
T.S. Jin, J.S. Zhang, A.Q. Wang, F.S. Zhang, Chin. J. Org. Chem. 25, 335 (2005)
J.J. Ma, X. Zhou, X.H. Zhang, C. Wang, Z. Wang, J.C. Li, Q. Li Aus. J. Chem. 60, 146 (2007)
M. Salami, A. Ezabadi, Polycyclic Aromat. Compd. 42, 3377 (2022)
S. Kamalifar, H. Kiyani, Polycyclic Aromat. Compd. 42, 3675 (2022)
F. Darviche, S. Balalaie, F. Chadegani, P. Salehi. Synth. Commun. 37, 1059 (2007)
J.E. Thai, M.C. Roach, M. M. Reynolds Front Chem. 11, 1259835 (2023)
M. Karegar, M.M. Khodaei, Res. Chem. Intermed. 47, 4537 (2021)
S.A. Shaikh, V.S. Kamble, S.T. Salunkhe, S.K. Patil, B.D. Aghav, Org. Prep. Proced. Int. 55, 393 (2023)
S. Kohli, N. Sharma, R. Chandra, Appl. Organomet. Chem. 37, e7049 (2023)
Y. Merroun, S. Chehab, A.E. Hallaoui, T. Guedira, S. Boukhris, R. Ghailane, A. Souizi, J. Mol. Struct. 1294, 136383 (2023)
P.G. Kargar, G. Bagherzade, H. Eshghi, RSC Adv. 11(8), 4339 (2021)
F. Mohamadpour, Org. Prep. Proced. Int. 53, 59 (2021)
G. Rathee, S. Kohli, N. Singh, A. Awasthi, R. Chandra, ACS Omega 5, 15673 (2020)
F.G. Kahangi, M. Mehrdad, M.M. Heravi, Sci. Rep. 10, 15285 (2020)
P. Bansal, G. Chaudhary, N. Kaur, S.K. Mehta, RSC Adv. 5, 8205 (2015)
F. Taghavi, M. Gholizadeh, A.S. Saljooghi, M. Ramezanib, RSC Adv. 6, 87082 (2016)
Z.G. Kohi, K.R. Moghadum, S.T. Roudsari, Mole. Catal. 548, 113417 (2023)
B. Maleki, S. Barzegar, Z. Sepehr, J. Iran. Chem. Soc. 9, 757 (2012)
E. Hataminejad, A. Ezabadi, Res. Chem. Intermed. 48, 2535 (2022)
M. Shiri, M.A. Zolfigol, Tetrahedron 65, 587 (2009)
H. Firouzabadi, N. Iranpoor, A. Garzan, Adv. Synth. Catal. 347, 1925 (2005)
K.L. Penniston, S.Y. Nakada, R.P. Holmes, D.G. Assimos, J. Endourol. 22(3), 567 (2008)
M.O.H. Helali, M. Ibrahim, M.Z. Shafique, M.M. Rahman, S.K. Biswas, M.S. Islam, J. bio. sci. 16, 125 (2008)
S. Ranganna, V.S. Govindarajan, K.V. Ramana, Crit. Rev. Food Sci. Nutr. 18(4), 313 (1983)
S. Ranganna, V.S. Govindarajan, K.V. Ramana, Crit. Rev. Food Sci. Nutr. 19(1), 1 (1983)
M.B. Deshmukh, S.S. Patil, S.D. Jadhav, P.B. Pawar, Synth. Commun. 42, 1177 (2012)
S. Patil, S. Jadhav, M.B. Deshmukh, J. Chem. Sci. 125, 851 (2013)
S.S. Patil, S.D. Jadhav, U.P. Patil, Arch. Appl. Sci. Res. 4, 1074 (2012)
S.D. Jadhav, R.C. Patil, A.A. Jagdale, S.S. Patil, Res. Chem. Intermed. 48, 593 (2022)
S.S. Patil, S.D. Jadhav, M.B. Deshmukh, Ind. J. Chem. Sec. B 52B, 1172 (2013)
S.T. Morbale, S.D. Jadhav, M.B. Deshmukh, S.S. Patil, RSC Adv. 5, 84610 (2015)
S.T. Morbale, S.K. Shinde, S.D. Jadhav, M.B. Deshmukh, S.S. Patil, Der Pharm. Lett. 7, 169 (2015)
B.M. Patil, S.K. Shinde, A.A. Jagdale, S.D. Jadhav, S.S. Patil, Res. Chem. Intermed. 47, 4369 (2021)
M. Bustamante, N. Duran, M.C. Diez, Soil Sci. Plant Nutr. 12, 667 (2012)
E. Fuguet, C. Ràfols, M. Rosés, E. Bosch, Anal. Chim. Acta 548, 95 (2005)
K. Hanna, R. Denoyel, I. Beurroies, J.P. Dubès, Coll. Surf. A Physicochem. Eng. Asp. 254, 231 (2005)
D.A. Edwards, R.G. Luthy, Z. Liu, Environ. Sci. Technol. 25, 127 (1991)
D.J.L. Prak, P.H. Pritchard, Water Res. 36, 3463 (2002)
L.A. Moreira, A. Firoozabadi, Langmuir 25, 12101 (2009)
Acknowledgements
The authors would like to express their thankfulness to the Indian Institute of Chemical Technology (IICT), Hyderabad, for the NMR analysis.
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SDJ and SSP contributed equally to the experiment design and direction, with SDJ and BMP performing the laboratory work. The authors jointly prepared the draft manuscript, and finalized the manuscript.
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Jadhav, S.D., Patil, B.M. & Patil, S.S. An eco-friendly approach to synthesize arylmethylene bis(3-hydroxy-5,5’-dimethyl-2-cyclohexene-1-ones) and 1,8-dioxo-octahydroxanthenes. Res Chem Intermed (2024). https://doi.org/10.1007/s11164-024-05274-w
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DOI: https://doi.org/10.1007/s11164-024-05274-w