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Green Protocol for the Synthesis of 1,8-Dioxo-Decahydroacridines by Hantzsch Condensation Using Citric Acid as Organocatalyst


Affiliations
1 Department of Chemistry, Rajaram College, Kolhapur 416 004, India
2 Department of Chemistry, P. D. V. P. College, Tasgaon 416 312, India
 

Herein we describe a clean and sustainable, one-pot, multi-component protocol for the synthesis of 1,8- dioxo-decahydroacridines by Hantzsch condensation of cyclic 1,3-dicarbonyl compound and NH4OAc with diverse aryl aldehydes using citric acid as an inexpensive green additive in ecological safe solvent. Utilization of cheaper and safer catalyst, cleaner reaction profile, straightforward work-up procedure and good to excellent yields of the desired product are the noteworthy aspects of this method.

Keywords

Acridines, Citric Acid, Organocatalysts, Green Protocol, Multi-Component Reactions.
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  • Liu, P., Hao, J. W., Mo, L. P. and Zhang, Z. H., Recent advances in the application of deep eutectic solvents as sustainable media as well as catalysts in organic reactions. RSC Adv., 2015, 5, 48675– 48704.

  • Vladu, M. I., ‘Green’ electronics: biodegradable and biocompatible materials and devices for sustainable future. Chem. Soc. Rev., 2014, 43, 588–610.

  • Khedkar, S. A. and Auti, P. B., 1, 4-Dihydropyridines: a class of pharmacologically important molecules. Mini. Rev. Med. Chem., 2014, 14, 282–290.

  • Huang, C., Yan, S. J., Li, Y. M., Huang, R. and Lin, J., Synthesis of polyhalo acridones as pH-sensitive fluorescence probes. Bioorg. Med. Chem. Lett., 2010, 20, 4665–4669.

  • Anandan, S., Madhavan, J., Maruthamuthu, P., Raghukumar, V. and Ramakrishnan, V. T., Synthesis and characterization of naphthyridine and acridinedione ligands coordinated ruthenium (II) complexes and their applications in dye-sensitized solar cells. Sol. Energy Mater. Sol. Cells, 2004, 81, 419–428.

  • Islam, A., Murugan, P., Hwang, K. C. and Cheng, C. H., Blue light-emitting devices based on 1,8-acridinedione derivatives. Synth. Met., 2003, 139, 347–353.

  • Rajendran, A. and Nair, B. U., Unprecedented dual binding behaviour of acridine group of dye: a combined experimental and theoretical investigation for the development of anticancer chemotherapeutic agents. Biochim. Biophys. Acta. Gen. – Subjects, 2006, 1760, 1794–1801.

  • Alvala, M., Bhatnagar, S., Ravi, A., Jeankumar, V. U., Manjashetty, T. H., Yogeeswari, P. and Sriram, D., Novel acridinedione derivatives: design, synthesis, SIRT1 enzyme and tumor cell growth inhibition studies. Bioorg. Med. Chem. Lett., 2012, 22, 3256– 3260.

  • Cholody, W. M., Horowska, B., Paradziej-Lukowicz, J., Martelli, S. and Konopa, J., Structure–activity relationship for antineoplastic imidazoacridinones: synthesis and antileukemic activity in vivo. J. Med. Chem., 1996, 39, 1028–1032.

  • Mikata, Y., Yokoyama, M., Mogami, K., Kato, M., Okura, I., Chikira, M. and Yano, S., Intercalator-linked cisplatin: synthesis and antitumor activity of cis-dichloroplatinum(II) complexes connected to acridine and phenylquinolines by one methylene chain. Inorg. Chem. Acta, 1998, 279, 51–57.

  • Lacasagne, A., Buu-Ho, N. P., Daudel, R. and Zajdela, F., The relation between carcinogenic activity and the physical and chemical properties of angular benzacridines. Adv. Cancer Res., 1956, 4, 315–369.

  • Berkan, O., Sarac, B., Simsek, R., Yildirim, S., Sariogli, Y. and Safak, C., Vasorelaxing properties of some phenylacridine type potassium channel openers in isolated rabbit thoracic arteries. Eur. J. Med., 2002, 37, 519–523.

  • Wainwright, M. J. J., Acridine – a neglected antibacterial chromophore. Antimicrob. Chemother., 2001, 47, 1–13.

  • Suarez, M., Loupy, A., Salfran, E., Moran, L. and Rolando, E., Synthesis of decahydroacridines under microwaves using ammonium acetate supported on alumina. Heterocycles, 1999, 51, 21– 27.

  • Bakibaev, A. A., Fillimonov, V. D. and Nevgodova, E. S., Ureas in the organic synthesis. Part 6. Reactions of 1,3-dicarbonyls with azomethines and urea in DMSO as a method for the synthesis of arylacridines. Zh. Org. Khim., 1991, 27, 1512–1519.

  • Martin, N. et al., Synthesis and conformational study of acridine derivatives related to 1,4-dihydropyridines. J. Heterocyclic Chem., 1995, 32, 235–238.

  • Tu, S. J., Lu, Z., Shi, D., Yao, C., Gao, Y. and Guo, C., A convenient synthesis of 9-aryl-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10decahydroacridine-1,8-diones under microwave irradiation without solvent. Synth. Commun., 2002, 32, 2181–2185.

  • Tu, S., Fang, F., Zhu, S., Li, T., Zhang, X. and Zhuang, Q., Onepot synthesis of a novel compound N-hydroxydecahydroacridine under microwave irradiation. J. Heterocyclic Chem., 2004, 41, 767–770.

  • Vekariya, R. H. and Patel, H. D., Sulfonated polyethylene glycol (PEG-OSO3H) as a polymer supported biodegradable and recyclable catalyst in green organic synthesis: recent advances. RSC Adv., 2015, 5, 49006–49030.

  • Soliman, H. A., Mubarak, A. Y., EL-Mekabati, A. and Elmorsy, S. S., SiO2/ZnCl2-catalyzed heterocyclic synthesis: green, rapid and efficient one-pot synthesis of 14-H-dibenzo[a, j]xanthenes, 1,8dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines under solvent-free conditions Chem. Sci. Trans., 2014, 3, 819– 825.

  • Khalafi-Nezhad, A., Panahi, F., Mohammadi, S. and Foroughi, H. O., A green and efficient procedure for one-pot synthesis of xanthenes and acridines using silica boron–sulfuric acid nanoparticles (SBSANs) as a solid lewis-protic acid. J. Iran. Chem. Soc., 2013, 10, 189–200.

  • Venkatesan, K., Pujari, S. S. and Srinivasan, K. V., Proline-catalyzed simple and efficient synthesis of 1,8-dioxo-decahydroacridines in aqueous ethanol medium. Synth. Commun., 2009, 1, 228–241.

  • Saeed, B., Fatemeh, C., Fatemeh, D. and Hamid Reza, B., One-pot synthesis of 1,8-dioxo-decahydroacridine derivatives in aqueous media. Chin. J. Chem., 2009, 27, 1953–1956.

  • Maripi, S., Korupolu, R. B. and Madasu, S. B., Nano nickel– cobalt ferrite catalysed one-pot multi-component synthesis of xanthenediones and acridinediones. Green Sustain. Chem., 2017, 7, 70–84.

  • Davoodnia, A., Khojastehnezhad, A. and Tavakoli-Hoseini, N., Carbon-based solid acid as an efficient and reusable catalyst for the synthesis of 1,8-dioxodecahydroacridines under solvent-free conditions. Bull. Korean Chem. Soc., 2011, 32, 2243–2248.

  • Shen, W., Wang, L. M., Tian, H., Tang, J. and Yu, J. J., Brønsted acidic imidazolium salts containing perfluoroalkyl tails catalyzed one-pot synthesis of 1,8-dioxo-decahydroacridines in water. J. Fluorine Chem., 2009, 130, 522–527.

  • Sehout, I., Boulcina, R., Boumoud, B., Boumoud, T. and Debache, A., Solvent-free synthesis of polyhydroquinoline and 1,8-dioxodecahydroacridine derivatives through the Hantzsch reaction catalyzed by a natural organic acid: a green method. Synth. Commun., 2017, 47, 1185–1191.

  • Gomez, S. M. M., Alzate-Sanchez, D. M., Rodriguez-Cordoba, W., Sierra, C. A. and Ochoa-Puentes, C., Competitive one-pot reactions: simultaneous synthesis of decahydroacridine-1,8-diones and 1,8-dioxo-octahydroxanthenes and photophysical characterization. Synth. Commun., 2014, 44, 648–659.

  • Chandrasekhar, S., Rao, Y. S., Sreelakshmi, L., Mahipal, B. and Reddy, C. R., Tris(pentafluorophenyl)borane-catalyzed threecomponent reaction for the synthesis of 1,8-dioxodecahydroacridines under solvent-free conditions. Synthesis, 2008, 11, 1737–1740.

  • Moeinpour, F. and Khojastehnezhad, A., An efficient one-pot synthesis of 1,8-dioxodecahydroacridines using silica-supported polyphosphoric acid (PPA–SiO2) under solvent-free conditions. E-J. Chem., 2012, 9, 504–509.

  • Banerjee, B. and Brahmachari, G., Ammonium chloride catalysed one-pot multicomponent synthesis of 1,8-dioxo-octahydroxanthenes and N-aryl-1,8-dioxodecahydroacridines under solvent free conditions. J. Chem. Res., 2014, 38, 745–764.

  • Javid, A., Khojastehnezhad, A., Heravi, M. and Bamoharram, F. F., Silica-supported Preyssler nanoparticles catalyzed simple and efficient one-pot synthesis of 1,8-dioxodecahydroacridines in aqueous media. Synth. React. Inorg. Met. Org. Chem., 2012, 42, 14–17.

  • Karhale, S., Patil, K., Bhenki, C., Rashinkar, G. and Helavi, V., Zirconocene catalyzed synthesis of 2-substituted benzimidazole derivatives. Res. Chem. Intermed., 2016, 42, 7257–7268.

  • Karhale, S., Survase, D., Bhat, R., Ubale, P. and Helavi, V., A practical and green protocol for the synthesis of 2,3-dihydroquinazolin4(1H)-ones using oxalic acid as organocatalyst. Res. Chem. Intermed., 2017, 43, 3915–3924.

  • Karhale, S., Patil, M., Rashinkar, G. and Helavi, V., Green and cost effective protocol for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines by using sawdust sulphonic acid. Res. Chem. Intermed., 2017, 43, 7073–7086.

  • Karhale, S., Bhenki, C., Rashinkar, G. and Helavi, V., Covalently anchored sulfamic acid on cellulose as heterogeneous solid acid catalyst for the synthesis of structurally symmetrical and unsymmetrical 1,4-dihydropyridine derivatives. New J. Chem., 2017, 41, 5133–5141.

  • Patil, M. A., Ubale, P. A., Karhale, S. S. and Helavi, V. B., Lemon juice: an environmentally benign catalyst for synthesis of benzothiazoles and benzoxazole derivatives in aqueous medium. Chem. Sin., 2017, 8, 198–205.


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  • Green Protocol for the Synthesis of 1,8-Dioxo-Decahydroacridines by Hantzsch Condensation Using Citric Acid as Organocatalyst

Abstract Views: 373  |  PDF Views: 114

Authors

Monika Patil
Department of Chemistry, Rajaram College, Kolhapur 416 004, India
Shrikrishna Karhale
Department of Chemistry, Rajaram College, Kolhapur 416 004, India
Ananada Kudale
Department of Chemistry, Rajaram College, Kolhapur 416 004, India
Arjun Kumbhar
Department of Chemistry, P. D. V. P. College, Tasgaon 416 312, India
Sagar More
Department of Chemistry, P. D. V. P. College, Tasgaon 416 312, India
Vasant Helavi
Department of Chemistry, Rajaram College, Kolhapur 416 004, India

Abstract


Herein we describe a clean and sustainable, one-pot, multi-component protocol for the synthesis of 1,8- dioxo-decahydroacridines by Hantzsch condensation of cyclic 1,3-dicarbonyl compound and NH4OAc with diverse aryl aldehydes using citric acid as an inexpensive green additive in ecological safe solvent. Utilization of cheaper and safer catalyst, cleaner reaction profile, straightforward work-up procedure and good to excellent yields of the desired product are the noteworthy aspects of this method.

Keywords


Acridines, Citric Acid, Organocatalysts, Green Protocol, Multi-Component Reactions.

References





DOI: https://doi.org/10.18520/cs%2Fv116%2Fi6%2F936-942