Abstract
An efficient catalytic system has been developed on the basis of carbon-doped MoO3 (CPM-3) for the synthesis of 1,8-dioxodecahydroacridines by condensation of dimedone, aromatic aldehydes, and anilines in ethanol–water (3:1) under ultrasonication. The effects of addition of polyethylene glycol (PEG-400) and carbon (0, 1, 2, and 3 wt %) as substrates were investigated systematically to get the desired carbon-doped MoO3 material. The carbon source was prepared from the plant Acacia arabica, and the obtained samples were calcined at 500°C. The catalytic material was characterized by a number of sophisticated techniques such as XRD, SEM-EDS, FT-IR, TEM, NH3-TPD, and BET. The present protocol has several advantages, including the use of a non-corrosive, nontoxic, inexpensive, and recyclable catalytic material.
Similar content being viewed by others
REFERENCES
Santana, L., Uriarte, E., Roleira, F., Milhazes, N., and Borges, F., Curr. Med. Chem., 2004, vol. 11, p. 3239. https://doi.org/10.2174/0929867043363721
El-salam, N., Mostafa, M., Ahmed, G., and Alothman, O., J. Chem., 2013, vol. 2013, article ID 890617. https://doi.org/10.1155/2013/890617
Azab, M., Youssef, M., and El-Bordany, E., Molecules, 2013, vol. 18, p. 832. https://doi.org/10.3390/molecules18010832
Salem, M., Sakr, S., El-Senousy, W., Madkour, H., Arch. Pharm. (Weinheim), 2013, vol. 346, p. 766. https://doi.org/10.1002/ardp.201300183
Cao, X., Sun, Z., Cao, Y., Wang, R., Cai, T., Chu, W., Hu, W., and Yang, Y., J. Med. Chem., 2014, vol. 57, p. 3687. https://doi.org/10.1021/jm4016284
El-Sawy, E., Ebaid, M., Abo-Salem, H., Al-Sehemi, A., and Mandour, A., Arab. J. Chem., 2013, vol. 7, p. 914. https://doi.org/10.1016/j.arabjc.2012.12.041
Chen, Y., Yu, K., Tan, N., Qiu, R., Liu, W., Luo, N., Tong, L., Au, C., Luo, Z., and Yin, S., Eur. J. Med. Chem., 2014, vol. 79, p. 391. https://doi.org/10.1016/j.ejmech.2014.04.026
El-Sawy, E., Mandour, A., El-Hallouty, S., Shaker, K., and Abo-Salem, H., Arab. J. Chem., 2013, vol. 6, p. 67. https://doi.org/10.1016/j.arabjc.2012.04.003
Mabkhot, Y., Barakat, A., Al-Majid, A., Alshahrani, S., Yousuf, S., and Choudhary, M., Chem. Cent. J., 2013, vol. 7, p. 112. https://doi.org/10.1186/1752-153X-7-112
Li, X., He, L., Chen, H., Wu, W., and Jiang, H., J. Org. Chem., 2013, vol. 78, p. 3636. https://doi.org/10.1021/jo400162d
Santos, C., Freitas, M., and Fernandes, E., Eur. J. Med. Chem., 2018, vol. 157, p. 1460. https://doi.org/10.1016/j.ejmech.2018.07.073
Kalaria, P., Karad, S., and Raval, D., Eur. J. Med. Chem., 2018, vol. 158, p. 917. https://doi.org/10.1016/j.ejmech.2018.08.040
Kerru, N., Bhaskaruni, S., Gummidi, L., Maddila, S., Maddila, S., and Jonnalagadda, S., Synth. Commun., 2019, vol. 49, p. 2437. https://doi.org/10.1080/00397911.2019.1639755
Kerru, N., Singh, P., Koorbanally, N., Raj, R., and Kumar, V., Eur. J. Med. Chem., 2017, vol. 142, p. 179. https://doi.org/10.1016/j.ejmech.2017.07.033
Eftekhari-Sis, B., Zirak, B., and Akbari, M.A., Chem. Rev., 2013, vol. 113, p. 2958. https://doi.org/10.1021/cr300176g
Kerru, N., Maddila, S., and Jonnalagadda, S.B., Curr. Org. Chem., 2019, vol. 23, p. 3154. https://doi.org/10.2174/1385272823666191202105820
Ju, Y. and Varma, R.S., J. Org. Chem., 2006, vol. 71, p. 135. https://doi.org/10.1021/jo051878h
Zarate, D.Z., Aguilar, R., Hernandez-Benitez, R.I., Labarrios, E.M., Delgado, F., and Tamariz, J., Tetrahedron, 2015, vol. 71, p. 6961. https://doi.org/10.1016/j.tet.2015.07.010
Leeson, P.D. and Springthorpe, B., Nat. Rev. Drug Discovery, 2007, vol. 6, p. 881. https://doi.org/10.1038/nrd2445
Kerru, N., Gummidi, L., Maddila, S., Gangu, K.K., and Jonnalagadda, S.B., Molecules, 2020, vol. 25, article no. 1909. https://doi.org/10.3390/molecules25081909
Pétrier, C. and Luche, J.L., Synthetic Organic Sonochemistry, Luche, J.-L., Ed., New York: Plenum Press, 1998, p. 51. https://doi.org/10.1007/978-1-4899-1910-6_2
Li, J.-T., Yang, W.-Z., Wang, S.-X., Li, S.-H., and Li, T.-S., Ultrason. Sonochem., 2002, vol. 9, p. 237. https://doi.org/10.1016/S1350-4177(02)00079-2
Fillion, H. and Luche, J.L., Synthetic Organic Sonochemistry, Luche, J.-L., Ed., New York: Plenum Press, 1998, p. 91. https://doi.org/10.1007/978-1-4899-1910-6_3
Cintas, P. and Luche, J.-L., Green Chem., 1999, vol. 1, p. 115. https://doi.org/10.1039/A900593E
Ohayon, E. and Gedanken, A., Ultrason. Sonochem., 2010, vol. 17, p. 173. https://doi.org/10.1016/j.ultsonch.2009.05.015
Askarinejad, A. and Morsali, A., Ultrason. Sonochem., 2009, vol. 16, p. 124. https://doi.org/10.1016/j.ultsonch.2008.05.015
Landau, M.V., Vradman, L., Herskowitz, M., and Koltypin, Y., J. Catal., 2001, vol. 201, p. 22. https://doi.org/10.1006/jcat.2001.3227
Antman, E., Muller, J., Goldberg, S., Macalpin, R., Rubenfire, M., Tabatznik, B., Liang, C., Heupler, F., Achuff, S., Reichek, N., Geltman, E., Kerin, N.Z., Neff, R.K., and Raunwald, E., Engl. J. Med., 1980, vol. 302, p. 1269. https://doi.org/10.1056/NEJM198006053022301
Hornung, R.S., Gould, B.A., Jones, R.I., Sonecha, T.N., and Raferty, E.B., Am. J. Cardiol., 1983, vol. 51, p. 1323. https://doi.org/10.1016/0002-9149(83)90306-5
Delfourne, E., Roubin, C., and Bastide, J., J. Org. Chem., 2000, vol. 65, p. 5476. https://doi.org/10.1021/jo000011a
Antonini, J., Polucci, P., Magnano, A., and Martelli, S., J. Med. Chem., 2001, vol. 44, p. 3329. https://doi.org/10.1021/jm010917o
Ferlin, M.G., Marzano, C., Chiarelotto, G., Baccichetti, F., and Bordin, F., Eur. J. Med. Chem., 2000, vol. 35, p. 827. https://doi.org/10.1016/S0223-5234(00)00170-7
Mikata, Y., Yokoyama, M., Mogami, K., Kato, M., Okura, I., Chikira, M., and Yano, S., Inorg. Chim. Acta, 1998, vol. 279, p. 51. https://doi.org/10.1016/S0020-1693(98)00035-8
Sirisha, K., Bikshapathi, D., Achaiah, G., and Reddy, V.M., Eur. J. Med. Chem., 2011, vol. 46, p. 1564. https://doi.org/10.1016/j.ejmech.2011.02.003
Spalding, D.P., Chapin, E.C., and Mosher, H.S., J. Org. Chem., 1954, vol. 19, p. 357. https://doi.org/10.1021/jo01368a011
Solanki, M.J., Vachharajani, P.R., Dubal, G.G., and Shah, V.H., Int. J. ChemTech. Res., 2011, vol. 3, p. 1139. https://www.sphinxsai.com/Vol.3No.3/Chem/pdf/CT=22(1139-1144)JS11.pdf
Ogawa, T., Nakato, A., Tsuchida, K., and Hatayama, K., Chem. Pharm. Bull., 1993, vol. 41, p. 108. https://doi.org/10.1248/cpb.41.108
Wainwright, M.J., Antimicrob. Chemother., 2001, vol. 47, p. 1. https://doi.org/10.1093/jac/47.1.1
Sirisha, K., Achaiah, G., and Reddy, V.M., Arch Pharm., 2010, vol. 343, p. 342. https://doi.org/10.1002/ardp.200900243
Davoodnia, A., Zare-Bidaki, A., and Behmadi, H., Chin. J. Catal., 2012, vol. 33, p. 1797. https://doi.org/10.1016/S1872-2067(11)60449-X
Godfraid, T., Miller, R., and Wibo, M., Pharmacol Rev., 1986, vol. 38, p. 321. https://pharmrev.aspetjournals.org/content/38/4/321
Shanmugasundaram, P., Murugan, P., and Ramakrishnan, V.T., Heteroat. Chem., 1996, vol. 7, p. 17. https://doi.org/10.1002/(SICI)1098-1071(199601)7:1<17::AID-HC3>3.0.CO;2-%23
Murugan, P., Shanmugasundaram, P., Ramakrishnan, V.T., Venkatachalapathy, B., Srividya, N., Ramamurthy, P., Gunasekaran, K., and Velmurugan, D., J. Chem. Soc., Perkin Trans. 2, 1998, vol. 2, p. 999. https://doi.org/10.1039/A701401E
Islam, A., Murugan, P., Hwang, K.C., and Cheng, C.H., Synth. Met., 2003, vol. 139, p. 347. https://doi.org/10.1016/S0379-6779(03)00112-7
Tu, S.J., Miao, C., Gao, Y., Fang, F., Zhuang, Q., Feng, Y., and Shi, D., Synlett, 2004, vol. 2004, no. 2, p. 255. https://doi.org/10.1055/s-2003-44981
Papagni, A., Campiglio, P., and Campione, M., J. Fluorine Chem., 2008, vol. 129, p. 294. https://doi.org/10.1016/j.jfluchem.2008.01.005
Reddy, B.V.S., Antony, A., and Yadav, J.S., Tetrahedron Lett., 2010, vol. 51, p. 3071. https://doi.org/10.1016/j.tetlet.2010.04.018
Niknam, K., Panahi, F., Saberi, D., and Mohagheghnejad, M., J. Heterocycl. Chem., 2010, vol. 47, p. 292. https://doi.org/10.1002/jhet.303
Balalaie, S., Chadegani, F., Darviche, F., and Bijanzadeh, H.R., Chin. J. Chem., 2009, vol. 27, p. 1953. https://doi.org/10.1002/cjoc.200990328
Das, B., Thirupathi, P., Mahender, I., Reddy, V.S., and Rao, Y.K., J. Mol. Catal. A: Chem., 2006, vol. 247, p. 233. https://doi.org/10.1016/j.molcata.2005.11.048
Dhruva, K. and Jagir, S., Synth. Commun., 2010, vol. 40, p. 510. https://doi.org/10.1080/00397910902987792
Shen, W. and Wang, W., Arkivoc, 2008, vol. 2008, part (xvi), p. 1. https://doi.org/10.3998/ark.5550190.0009.g01
Shen, W., Wang, L., Tian, H., Tang, J., and Yu, J., J. Fluorine Chem., 2009, vol. 130, p. 522. https://doi.org/10.1016/j.jfluchem.2009.02.014
Alinezhada, H., Tajbakhsha, M., Norouzia, M., Bagheryc, S., and Rakhtshah, J., J. Chem. Sci., 2013, vol. 125, p. 1517. https://doi.org/10.1007/s12039-013-0517-4
Wang, X.S., Zhang, M-M., Zeng, Z-S., Shi, D-Q, Tu, S-J., Wei, X-Y., and Zong, Z-M., Arkivoc, 2006, vol. 2006, no. 2, p. 117. https://doi.org/10.3998/ark.5550190.0007.213
Venkatesan, K., Pujari, S.S., and Srinivasan, K.V., Synth. Commun., 2009, vol. 39, p. 228. https://doi.org/10.1080/00397910802044306
Safaei-Ghomi, J., Ghasemzadeh, M.A., and Zahedi, S., J. Mex. Chem. Soc., 2013, vol. 57, p. 1. https://doi.org/10.29356/jmcs.v57i1.228
Fan, X., Li, Y., Zhang, X., Qu, G., and Wang, J., Heteroat. Chem., 2007, vol. 18, p. 786. https://doi.org/10.1002/hc.20410
Ghasemzadeh, M.A., Safaei-Ghomi, J., and Molaei, H., C. R. Chim., 2012, vol. 15, p. 969. https://doi.org/10.1016/j.crci.2012.08.010
Rashedian, F., Saberib, D., and Niknam, K., J. Chin. Chem. Soc., 2010, vol. 57, p. 998. https://doi.org/10.1002/jccs.201000139
Miao, C.B., Tu, S.J., Gao, Y., Feng, Y.J., and Feng, J.C., Chin. J. Chem., 2002, vol. 20, p. 703. https://doi.org/10.1002/cjoc.20020200716
Wang, X.S., Shi, D.Q., Wang, S.H., and Tu, S.J., Chin. J. Org. Chem., 2003, vol. 23, p. 1291. http://sioc-journal.cn/Jwk_yjhx/EN/abstract/article_327622.shtml
Subramanyam, M., Varala, R., Sreenivasulu, R., Rao, M.V.B., and Rao, K.P.A., Lett. Org. Chem., 2018, vol. 15, p. 915. https://doi.org/10.2174/1570178615666180212153735
Jin, T.S., Zhang, J.S., Guo, T.T., Wang, A.Q., and Li, T.S., Synthesis, 2004, vol. 2004, no. 12, p. 2001. https://doi.org/10.1055/s-2004-829151
Zhang, J., Li, C., Guan, W., Chen, X., Tsang, C-W., and Liang, C., Ind. Eng. Chem. Res., 2020, vol. 59, p. 4313. https://doi.org/10.1021/acs.iecr.9b06442
Lee, W.-S., Wang, Z., Wu, R.J., and Bhan, A., J. Catal., 2014, vol. 319, p. 44. https://doi.org/10.1016/j.jcat.2014.07.025
Boullosa-Eiras, S., Lødeng, R., Bergem, H., Stöcker, M., Hannevold, L., and Blekkan, E.A., Catal. Today, 2014, vol. 223, p. 44. https://doi.org/10.1016/j.cattod.2013.09.044
Xiao, L.-P., Wang, S., Li, H., Li, Z., Shi, Z.-J., Xiao, L., Sun, R.C., Fang, Y., and Song, G., ACS Catal., 2017, vol. 7, p. 7535. https://doi.org/10.1021/acscatal.7b02563
Mortensen, P.M., de Carvalho, H.W.P., Grunwaldt, J.-D., Jensen, P.A., and Jensen, A.D., J. Catal., 2015, vol. 328, p. 208. https://doi.org/10.1016/j.jcat.2015.02.002
Nolte, M.W., Zhang, J., and Shanks, B.H., Green Chem., 2016, vol. 18, p. 134. https://doi.org/10.1039/C5GC01614B
Sedri, A., Naeimi, A., and Mohammadi, S.Z., Carbohydr. Polym., 2018, vol. 199, p. 236. https://doi.org/10.1016/j.carbpol.2018.06.104
Lande, M.K., Navgire, M.E., Rathod, S.B., Katkar, S.S., Yelwande, A.A., and Arbad, B.R., J. Ind. Eng. Chem., 2012, vol. 18, p. 277. https://doi.org/10.1016/j.jiec.2011.11.048
Yelwande, A.A. and Lande, M.K., Res. Chem. Intermed., 2020, vol. 46, p. 5479. https://doi.org/10.1007/s11164-020-04273-x
Navgire, M.E., Yelwande, A.A., Arbad, B.R., and Lande, M.K., Chin. J. Chem., 2011, vol. 29, p. 2049. https://doi.org/10.1002/cjoc.201180355
Kihlborg, L., Ark. Kemi, 1963, vol. 21, p. 471.
Klug, H.P. and Alexander, L.E., X-Ray Diffraction Procedures for Polycrystalline and Amorphous Materials, New York, Wiley, 1974, 2nd ed.
Taylor, A., X-Ray Metallography, John Wiley, New York, 1961, p. 678.
Cullity, B.D., Elements of X-Ray Diffraction, Reading MA: Addison-Wesley, 1978, p. 284, 2nd ed.
Oyama, S.T., Radhakrishnan, S., Seman, M., Kondo, J.N., Domen, K., and Asakura, K., J. Phys. Chem. B, 2003, vol. 107, p. 1845. https://doi.org/10.1021/jp0220276
Ganguly, A. and George, R., Bull. Mater. Sci., 2007, vol. 30, p. 183. https://doi.org/10.1007/s12034-007-0033-6
Cheng, T., Fang, Z., Zou, G., Hu, Q., Hu, B., Yang, B., and Zhang, Y., Bull. Mater. Sci., 2006, vol. 29, p. 701. https://www.ias.ac.in/article/fulltext/boms/029/07/0701-0704
Gorska, P., Zaleska, A., and Kowalska, E., Appl. Catal., B., 2008, vol. 84, p. 440. https://doi.org/10.1016/j.apcatb.2008.04.028
Andrews, K.W., Dyson, D.J., and Keown, S.R., Interpretation of Electron Diffraction Patterns, New York: Plenum Press, 1971, 2nd ed.
Bian, G.-Z., Fan, L., Fu, Y.-L., and Fujimoto, K., Ind. Eng. Chem. Res., 1998, vol. 37, p. 1736. https://doi.org/10.1021/ie970792e
Schuh, K., Kleist, W., Høj, M., Jensen, A.D., Beato, P., Patzke, G.R., and Grunwaldt, J.-D., J. Solid State Chem., 2015, vol. 228, p. 42. https://doi.org/10.1016/j.jssc.2015.04.011
Oyama, S., Bull. Chem. Soc. Jpn., 1988, vol. 61, p. 2585. https://doi.org/10.1246/bcsj.61.2585
Abon, M., Mingot, B., Massardier, J., and Volta, J., Stud. Surf. Sci. Catal., 1990, vol. 55, p. 747. https://doi.org/10.1016/S0167-2991(08)60209-8
Tsutsumi, K., Characterization of Heterogeneous Catalysts, Tokyo: Kodansha, 1985.
Zhang, J., Li, C., Guan, W., Chen, X., Chen, X., and Tsang, C., Ind. Eng. Chem. Res., 2020, vol. 59, p. 4313. https://doi.org/10.1021/acs.iecr.9b06442
Navgire, M.E., Lande, M.K., Gambhire, A.B., Rathod, S.B., Aware, D.V., and Bhitre, S.R., Bull. Mater. Sci., 2011, vol. 34, p. 535. https://doi.org/10.1007/s12034-011-0108-2
ACKNOWLEDGMENTS
The authors are grateful to the Head, Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, India, and Principal, Jijamata College of Science and Arts, Bhende, Newasa, Ahmednagar, for providing all required facilities to carry out this study.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare the absence of conflict of interest.
Rights and permissions
About this article
Cite this article
Navgire, M.E., Bhitre, S.R., Yelwande, A.A. et al. One-Pot Synthesis of 1,8-Dioxodecahydroacridines Catalyzed by Carbon-Doped MoO3. Russ J Org Chem 58, 394–404 (2022). https://doi.org/10.1134/S1070428022030198
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428022030198