How to cite this paper
Aute, D., Parhad, A., Vikhe, V., Uphad, B & Gadhave, A. (2024). Aluminized polyborate catalyzed efficient solvent-free synthesis of 1,8-dioxo-decahydroacridines via hantzsch condensation.Current Chemistry Letters, 13(2), 417-424.
Refrences
1. Insuasty, D., Castillo, J., Becerra, D., Rojas, H., and Abonia, R. (2020) Synthesis of biologically active molecules through multicomponent reactions. Mol 25:505, 1-71.
2. Bosica, G., and Roderick, A. (2022) Recent advances in multicomponent reactions catalysed under operationally heterogeneous conditions. Catalysts 12(7):725, 1-30.
3. Gensicka-Kowalewska, M., Cholewinski, G., and Dzierzbicka, K. (2017) Recent developments in the synthesis and biological activity of acridine/acridone analogues. RSC Adv., 7 15776-15804.
4. Wang, F. M., Zhou, L., Li, J. F., Bao, D., and Chen, L. Z. (2017) Synthesis, structure, and biological activities of 10-substituted 3,3,6,6-tetramethyl-9-aryl-3, 4, 6, 7, 9, 10- hexahydroacridine-1,8(2H,5H)-dione derivatives. J. Heterocyclic Chem., 54(6) 3120-3125.
5. Iqbal, N., Ali, S. A., Munir, I., Khan, S., Ayub, K., Al-Rashida, M., Islam, M., Shafiq, Z., Ludwing, R., and Hammed, A. (2018) Acridinedione as selective fluoride ion chemosensor: a detailed spectroscopic and quantum mechanical investigation. RSC Adv., 8 1993-2003.
6. Vaid, R., Gupta, M., and Gupta, V. K. (2017) Immobilization of organo functionalized silica (SiMPTMS) with biphenyl 2,2′ dioic acid and investigation of its catalytic property for one pot tandem synthesis of acridine 1,8 dione derivatives. J. Iran. Chem. Soc., 14(10) 2199-2210.
7. Mali, A. S., Potnis, C. S., and Chaturbhuj, G. U. (2018) Aluminized polyborate: a novel catalyst for the multicomponent solvent free synthesis of alkyl 1,2,6 trisubstituted 4 [(hetero) arylamino] 1,2,5,6 tetrahydropyridine 3 carboxylates. J. Iran. Chem. Soc., 15(6) 1399-1409.
8. Aute, D., Kshirsagar, A., Uphade, B., and Gadhave, A. (2020) Aluminized polyborate catalysed green and efficient synthesis of polyhydroquinolines under solvent free conditions. Res. Chem. Intermed., 46(7) 3491-3508.
9. Aute, D., Kshirsagar, A., Uphade, B., and Gadhave, A. (2020) Ultrasound assisted and aluminized polyborate prompted green and efficient one pot protocol for the synthesis of hexahydroquinolines. Polycycl. Aromat. Comp., 42(4) 1375-1390.
10. Aute, D., Kshirsagar, A., Uphade, B., and Gadhave, A. (2020) An expedient and straightforward solvent-free synthesis of 1,8-dioxo-octahydroxanthenes using eco-friendly aluminized polyborate catalyst. J. Heterocyclic Chem., 57(10) 3691-3702.
11. Madankumar, N., and Pitchumani, K. (2018) β-cyclodextrin monosulphonic acid promoted multicomponent synthesis of 1,8-dioxodecahydroacridines in water. ChemistrySelect., 3 10886-10891.
12. Lavanya, G., Venkatapathy, K., Magesh, C. G., Perumal, P. T., R. Sathishkumar, R., and Amudha, P. (2019) The first recyclable, nanocrystalline CdS thin film mediated eco-benign synthesis of Hantzsch 1, 4 dihyropyridines, 1, 8‐dioxodecahydroacridine and polyhydroquinolines derivatives. Appl Organometal Chem., 33(9) e5026.
13. Gholami Dehbalaei, M., Foroughifar, N., Pasdar, H., and Khajeh-Amiri, A. (2018) N-propyl benzoguanamine sulfonic acid supported on magnetic Fe3O4 nanoparticles: a novel and efficient magnetically heterogeneous catalyst for the synthesis of 1,8-dioxo-decahydroacridine derivatives. New J. Chem., 42(1) 327-335.
14. Choudhury, P. Ghosh, P., and Basu, B. (2020) Amine functionalized graphene oxide nanosheets (AFGONs): an efficient bifunctional catalyst for selective formation of 1,4 dihydropyridines, acridinediones and polyhydroquinolines. Mol. Divers., 24 283-294.
15. Eyvazzadeh-Keihan, R., Bahrami, N., Taheri-Ledari, R., and Maleki, A. (2020) Highly facilitated synthesis of phenyl(tetramethyl)acridinedione pharmaceuticals by a magnetized nanoscale catalytic systedm, constructed of GO, Fe3O4 and creatine. Diam. Relat. Mater., 102 107661.
16. Magyar, A., and Hell, Z. (2019) An efficient one pot four component synthesis of 9 aryl hexahydroacridine 1,8 dione derivatives in the presence of a molecular sieves supported iron catalyst. Catal. Letters., 149 2528-2534.
17. Alirezvani, Z., Dekamin, M. G., and Valiey, E. (2019) New hydrogen-bond-enriched 1,3,5-tris(2-hydroxyethyl) isocyanurate covalently functionalized MCM-41: an efficient and recoverable hybrid catalyst for convenient synthesis of acridinedione derivatives. ACS Omega., 4(24) 20618-20633.
18. Kilbas, B., Ergen, S., and Cakici, D. (2019) Highly efficient and reusable Pd/AlO(OH) catalyzed synthesis of acridinedione derivatives. Curr. Organocatalysis., 6 257-265.
19. Zhu, G., and Li, Y. (2020) Urease: a highly efficient biocatalyst for synthesis of polyhydroquinolines and polyhydroacridines from the ammonia formed in situ. Mol. Divers., 25 2149-2159.
20. Gilanizadeh, M., and Zeynizadeh, B. (2019) Synthesis of acridinediones and biscoumarins Using Fe3O4@SiO2@Ni–Zn–Fe LDH as an efficient magnetically recoverable mesoporous catalyst. Polycycl. Aromat. Comp., 41(1) 15-32.
21. Mohammadi, H., and Shaterian, H. R. (2019) Ferric (III) complex supported on superparamagnetic Fe3O4@SiO2 as a reusable Lewis acid catalyst: a new highly efficient protocol for the synthesis of acridinedione and spiroquinazolin 4(3H) one derivatives. Res. Chem. Intermed., 46(1) 179-195.
22. Patil, M., Karhale, S., Kudale, A., Kumbhar, A., More, S., and Helavi, V. (2019) Green protocol for the synthesis of 1,8-dioxo-decahydroacridines by Hantzsch condensation using citric acid as organocatalyst. Curr. Sci., 116 936-942.
23. Pavithra, D., and Ethiraj, K. R. (2020) Facile Synthesis of xanthenesdiones and acridinediones through TEMPO/CuCl2 catalyzed aerobic oxidation of benzyl alcohols and cyclization with cyclohexane-1,3-dicarbonyl compounds. Polycycl. Aromat. Comp., 42(4) 1078-1090.
24. Shirole, G. D., Bhalekar, S., and Shelke, S. N. (2018) N-Butylpyridinium heptachlorodialuminate : A convenient catalyst for the synthesis of acridine 1,8 diones derivatives by microwave assisted Hantzsch reaction. Indian. J. Chem., 57B 1430-1435.
25. Reddy, M. M., and Sivaramakrishna, A. (2020) A facile L-proline catalyzed one-pot synthesis of xanthene and acridine based quinolones via knoevenagel condensation reaction. ChemistrySelect., 5 4816-4821.
26. Zeynizadeh, B., and Gilanizadeh, M. (2020) Microwave-promoted three-component Hantzsch synthesis of acridinediones under green conditions. Curr. Chem. Lett., 9 71-78.
27. Mazloumi, M., and Shirini, F. (2020) Introduction of a new catalyst containing an ionic liquid bridge on nanoporous Na+-montmorillonite for the synthesis of hexahydroquinolines and 1,8-dioxo-decahydroacridines via Hantzsch condensation. J. Mol. Struct., 1217 128326.
28. Mousavi, S. R., Nodeh, H. R., and Foroumadi, A. (2019) Magnetically recoverable graphene-based nanoparticles for the one-pot synthesis of acridine derivatives under solvent-free conditions. Polycycl. Aromat. Comp., 41(4) 746-760.
29. Chehab, S., Merroun, Y., Ghailane, T., Ghailane, R., Boukhris, S., Akhazzane, M., Kerbal, A., and Souizi, A. (2019) Synthesis of 9-Arylhexahydroacridine-1,8-diones using phosphate fertilizers as heterogeneous catalysts. Russ. J. Org., 55(9) 1380-1386.
30. Bhosle, M. R., Nipte, D., Gaikwad, J., Shaikh, M. A., Bondle, G. M., and Sangshetti, J. N. (2018) A rapid and green method for expedient multicomponent synthesis of N-substituted decahydroacridine-1,8-diones as potential antimicrobial agents. Res. Chem. Intermed., 44 7047-7064.
31. Mohammadi, H., and Shaterian, H. R. (2020) Sulfonated magnetic nanocatalyst and application for synthesis of novel Spiro[acridine 9,5′ thiazole] 1,4′ dione derivatives. Res. Chem. Intermed., 46 1109-1195.
32. Chavan, P. N., Pansare, D. N., and Shelke, R. N. (2019) Eco-friendly, ultrasound-assisted, and facile synthesis of one-pot multicomponent reaction of acridine-1,8(2H,5H)-diones in an aqueous solvent. J. Chin. Chem. Soc., 66(8) 822-828.
33. Xiong, H., Han, J., Wang, J., Lu, W., Wang, C., Chen, Y., Lian, F., Zhang, N., Liu,Y.C., Zhang, C., Ding, H., Jiang, H., Lu, W., Luo, C., and Zhou, B. (2018) Discovery of 1,8-acridinedione derivatives as novel GCN5 inhibitors via high throughput screening. Eur. J. Med. Chem., 151 740-751.
34. Parhad, A., Aute, D., Gadhave, A., and Uphade, B. (2023) Fe Doped Ga2O3 Nanomaterial Catalysed Green and Efficient One Pot Three Component Synthesis of Tetrahydrobenzo[b]Pyran. Lett. Org. Chem., 20 (2) 143-153.
35. Tambe, A., Dange, C., Gavande, J., Dhawale, R., Kadnor, V., Gadhave, A., and Shirole, G. (2023 ) Novel Pumice Supported Perchloric Acid Promoted Protocol for the Synthesis of Tetrahydrobenzo[b]Pyran via Multi-Component Approach. Polycycl. Aromat. Comp., 1-16. (Accepted paper) DOI:10.1080/10406638.2023.2179080
36. Pinjari, S., Shirole, G., Uphade, B., and Gadhave A. (2023) Fe3O4@TiO2 nanoparticles catalyzed and NaBH4 assisted one-pot reductive amination of aldehydes at ambient condition. Res. Chem. Intermed., (Accepted paper) https://doi.org/10.1007/s11164-023-05123-2
2. Bosica, G., and Roderick, A. (2022) Recent advances in multicomponent reactions catalysed under operationally heterogeneous conditions. Catalysts 12(7):725, 1-30.
3. Gensicka-Kowalewska, M., Cholewinski, G., and Dzierzbicka, K. (2017) Recent developments in the synthesis and biological activity of acridine/acridone analogues. RSC Adv., 7 15776-15804.
4. Wang, F. M., Zhou, L., Li, J. F., Bao, D., and Chen, L. Z. (2017) Synthesis, structure, and biological activities of 10-substituted 3,3,6,6-tetramethyl-9-aryl-3, 4, 6, 7, 9, 10- hexahydroacridine-1,8(2H,5H)-dione derivatives. J. Heterocyclic Chem., 54(6) 3120-3125.
5. Iqbal, N., Ali, S. A., Munir, I., Khan, S., Ayub, K., Al-Rashida, M., Islam, M., Shafiq, Z., Ludwing, R., and Hammed, A. (2018) Acridinedione as selective fluoride ion chemosensor: a detailed spectroscopic and quantum mechanical investigation. RSC Adv., 8 1993-2003.
6. Vaid, R., Gupta, M., and Gupta, V. K. (2017) Immobilization of organo functionalized silica (SiMPTMS) with biphenyl 2,2′ dioic acid and investigation of its catalytic property for one pot tandem synthesis of acridine 1,8 dione derivatives. J. Iran. Chem. Soc., 14(10) 2199-2210.
7. Mali, A. S., Potnis, C. S., and Chaturbhuj, G. U. (2018) Aluminized polyborate: a novel catalyst for the multicomponent solvent free synthesis of alkyl 1,2,6 trisubstituted 4 [(hetero) arylamino] 1,2,5,6 tetrahydropyridine 3 carboxylates. J. Iran. Chem. Soc., 15(6) 1399-1409.
8. Aute, D., Kshirsagar, A., Uphade, B., and Gadhave, A. (2020) Aluminized polyborate catalysed green and efficient synthesis of polyhydroquinolines under solvent free conditions. Res. Chem. Intermed., 46(7) 3491-3508.
9. Aute, D., Kshirsagar, A., Uphade, B., and Gadhave, A. (2020) Ultrasound assisted and aluminized polyborate prompted green and efficient one pot protocol for the synthesis of hexahydroquinolines. Polycycl. Aromat. Comp., 42(4) 1375-1390.
10. Aute, D., Kshirsagar, A., Uphade, B., and Gadhave, A. (2020) An expedient and straightforward solvent-free synthesis of 1,8-dioxo-octahydroxanthenes using eco-friendly aluminized polyborate catalyst. J. Heterocyclic Chem., 57(10) 3691-3702.
11. Madankumar, N., and Pitchumani, K. (2018) β-cyclodextrin monosulphonic acid promoted multicomponent synthesis of 1,8-dioxodecahydroacridines in water. ChemistrySelect., 3 10886-10891.
12. Lavanya, G., Venkatapathy, K., Magesh, C. G., Perumal, P. T., R. Sathishkumar, R., and Amudha, P. (2019) The first recyclable, nanocrystalline CdS thin film mediated eco-benign synthesis of Hantzsch 1, 4 dihyropyridines, 1, 8‐dioxodecahydroacridine and polyhydroquinolines derivatives. Appl Organometal Chem., 33(9) e5026.
13. Gholami Dehbalaei, M., Foroughifar, N., Pasdar, H., and Khajeh-Amiri, A. (2018) N-propyl benzoguanamine sulfonic acid supported on magnetic Fe3O4 nanoparticles: a novel and efficient magnetically heterogeneous catalyst for the synthesis of 1,8-dioxo-decahydroacridine derivatives. New J. Chem., 42(1) 327-335.
14. Choudhury, P. Ghosh, P., and Basu, B. (2020) Amine functionalized graphene oxide nanosheets (AFGONs): an efficient bifunctional catalyst for selective formation of 1,4 dihydropyridines, acridinediones and polyhydroquinolines. Mol. Divers., 24 283-294.
15. Eyvazzadeh-Keihan, R., Bahrami, N., Taheri-Ledari, R., and Maleki, A. (2020) Highly facilitated synthesis of phenyl(tetramethyl)acridinedione pharmaceuticals by a magnetized nanoscale catalytic systedm, constructed of GO, Fe3O4 and creatine. Diam. Relat. Mater., 102 107661.
16. Magyar, A., and Hell, Z. (2019) An efficient one pot four component synthesis of 9 aryl hexahydroacridine 1,8 dione derivatives in the presence of a molecular sieves supported iron catalyst. Catal. Letters., 149 2528-2534.
17. Alirezvani, Z., Dekamin, M. G., and Valiey, E. (2019) New hydrogen-bond-enriched 1,3,5-tris(2-hydroxyethyl) isocyanurate covalently functionalized MCM-41: an efficient and recoverable hybrid catalyst for convenient synthesis of acridinedione derivatives. ACS Omega., 4(24) 20618-20633.
18. Kilbas, B., Ergen, S., and Cakici, D. (2019) Highly efficient and reusable Pd/AlO(OH) catalyzed synthesis of acridinedione derivatives. Curr. Organocatalysis., 6 257-265.
19. Zhu, G., and Li, Y. (2020) Urease: a highly efficient biocatalyst for synthesis of polyhydroquinolines and polyhydroacridines from the ammonia formed in situ. Mol. Divers., 25 2149-2159.
20. Gilanizadeh, M., and Zeynizadeh, B. (2019) Synthesis of acridinediones and biscoumarins Using Fe3O4@SiO2@Ni–Zn–Fe LDH as an efficient magnetically recoverable mesoporous catalyst. Polycycl. Aromat. Comp., 41(1) 15-32.
21. Mohammadi, H., and Shaterian, H. R. (2019) Ferric (III) complex supported on superparamagnetic Fe3O4@SiO2 as a reusable Lewis acid catalyst: a new highly efficient protocol for the synthesis of acridinedione and spiroquinazolin 4(3H) one derivatives. Res. Chem. Intermed., 46(1) 179-195.
22. Patil, M., Karhale, S., Kudale, A., Kumbhar, A., More, S., and Helavi, V. (2019) Green protocol for the synthesis of 1,8-dioxo-decahydroacridines by Hantzsch condensation using citric acid as organocatalyst. Curr. Sci., 116 936-942.
23. Pavithra, D., and Ethiraj, K. R. (2020) Facile Synthesis of xanthenesdiones and acridinediones through TEMPO/CuCl2 catalyzed aerobic oxidation of benzyl alcohols and cyclization with cyclohexane-1,3-dicarbonyl compounds. Polycycl. Aromat. Comp., 42(4) 1078-1090.
24. Shirole, G. D., Bhalekar, S., and Shelke, S. N. (2018) N-Butylpyridinium heptachlorodialuminate : A convenient catalyst for the synthesis of acridine 1,8 diones derivatives by microwave assisted Hantzsch reaction. Indian. J. Chem., 57B 1430-1435.
25. Reddy, M. M., and Sivaramakrishna, A. (2020) A facile L-proline catalyzed one-pot synthesis of xanthene and acridine based quinolones via knoevenagel condensation reaction. ChemistrySelect., 5 4816-4821.
26. Zeynizadeh, B., and Gilanizadeh, M. (2020) Microwave-promoted three-component Hantzsch synthesis of acridinediones under green conditions. Curr. Chem. Lett., 9 71-78.
27. Mazloumi, M., and Shirini, F. (2020) Introduction of a new catalyst containing an ionic liquid bridge on nanoporous Na+-montmorillonite for the synthesis of hexahydroquinolines and 1,8-dioxo-decahydroacridines via Hantzsch condensation. J. Mol. Struct., 1217 128326.
28. Mousavi, S. R., Nodeh, H. R., and Foroumadi, A. (2019) Magnetically recoverable graphene-based nanoparticles for the one-pot synthesis of acridine derivatives under solvent-free conditions. Polycycl. Aromat. Comp., 41(4) 746-760.
29. Chehab, S., Merroun, Y., Ghailane, T., Ghailane, R., Boukhris, S., Akhazzane, M., Kerbal, A., and Souizi, A. (2019) Synthesis of 9-Arylhexahydroacridine-1,8-diones using phosphate fertilizers as heterogeneous catalysts. Russ. J. Org., 55(9) 1380-1386.
30. Bhosle, M. R., Nipte, D., Gaikwad, J., Shaikh, M. A., Bondle, G. M., and Sangshetti, J. N. (2018) A rapid and green method for expedient multicomponent synthesis of N-substituted decahydroacridine-1,8-diones as potential antimicrobial agents. Res. Chem. Intermed., 44 7047-7064.
31. Mohammadi, H., and Shaterian, H. R. (2020) Sulfonated magnetic nanocatalyst and application for synthesis of novel Spiro[acridine 9,5′ thiazole] 1,4′ dione derivatives. Res. Chem. Intermed., 46 1109-1195.
32. Chavan, P. N., Pansare, D. N., and Shelke, R. N. (2019) Eco-friendly, ultrasound-assisted, and facile synthesis of one-pot multicomponent reaction of acridine-1,8(2H,5H)-diones in an aqueous solvent. J. Chin. Chem. Soc., 66(8) 822-828.
33. Xiong, H., Han, J., Wang, J., Lu, W., Wang, C., Chen, Y., Lian, F., Zhang, N., Liu,Y.C., Zhang, C., Ding, H., Jiang, H., Lu, W., Luo, C., and Zhou, B. (2018) Discovery of 1,8-acridinedione derivatives as novel GCN5 inhibitors via high throughput screening. Eur. J. Med. Chem., 151 740-751.
34. Parhad, A., Aute, D., Gadhave, A., and Uphade, B. (2023) Fe Doped Ga2O3 Nanomaterial Catalysed Green and Efficient One Pot Three Component Synthesis of Tetrahydrobenzo[b]Pyran. Lett. Org. Chem., 20 (2) 143-153.
35. Tambe, A., Dange, C., Gavande, J., Dhawale, R., Kadnor, V., Gadhave, A., and Shirole, G. (2023 ) Novel Pumice Supported Perchloric Acid Promoted Protocol for the Synthesis of Tetrahydrobenzo[b]Pyran via Multi-Component Approach. Polycycl. Aromat. Comp., 1-16. (Accepted paper) DOI:10.1080/10406638.2023.2179080
36. Pinjari, S., Shirole, G., Uphade, B., and Gadhave A. (2023) Fe3O4@TiO2 nanoparticles catalyzed and NaBH4 assisted one-pot reductive amination of aldehydes at ambient condition. Res. Chem. Intermed., (Accepted paper) https://doi.org/10.1007/s11164-023-05123-2