Ultrasound-promoted novel route to triazabenzo[b]cyclopenta[lm]fluorenes: An efficient NiFe2O4@SiO2–SO3H nanocatalyst-assisted green synthesis
Soumyadip Basu
Department of Chemistry, University of Calcutta, Kolkata, India
Contribution: Formal analysis (lead), Methodology (lead)
Search for more papers by this authorSauvik Chatterjee
Department of Materials Science, Indian Association for the Cultivation of Science, Kolkata, India
Contribution: Data curation (supporting)
Search for more papers by this authorAsim Bhaumik
Department of Materials Science, Indian Association for the Cultivation of Science, Kolkata, India
Contribution: Formal analysis (supporting), Investigation (supporting), Project administration (supporting)
Search for more papers by this authorCorresponding Author
Chhanda Mukhopadhyay
Department of Chemistry, University of Calcutta, Kolkata, India
Correspondence
Chhanda Mukhopadhyay, Department of Chemistry, University of Calcutta, 92 APC Road, Kolkata 700009, India.
Email: [email protected]
Contribution: Conceptualization (lead), Project administration (lead), Supervision (lead)
Search for more papers by this authorSoumyadip Basu
Department of Chemistry, University of Calcutta, Kolkata, India
Contribution: Formal analysis (lead), Methodology (lead)
Search for more papers by this authorSauvik Chatterjee
Department of Materials Science, Indian Association for the Cultivation of Science, Kolkata, India
Contribution: Data curation (supporting)
Search for more papers by this authorAsim Bhaumik
Department of Materials Science, Indian Association for the Cultivation of Science, Kolkata, India
Contribution: Formal analysis (supporting), Investigation (supporting), Project administration (supporting)
Search for more papers by this authorCorresponding Author
Chhanda Mukhopadhyay
Department of Chemistry, University of Calcutta, Kolkata, India
Correspondence
Chhanda Mukhopadhyay, Department of Chemistry, University of Calcutta, 92 APC Road, Kolkata 700009, India.
Email: [email protected]
Contribution: Conceptualization (lead), Project administration (lead), Supervision (lead)
Search for more papers by this authorFunding information: DST-PURSE DST Purse II, Grant/Award Number: SR/PURSE Phase 2/21(C); DST-FIST, Grant/Award Number: SR/FST/CSI-198/2008; CAS-V, Grant/Award Number: 540/3/CAS-V/2015; University Grants Commission (UGC), New Delhi
Abstract
A series of new triazabenzo[b]cyclopenta[lm]fluorene scaffolds have been synthesized from 1,2-phenylenediamines, isothiocyanates and ninhydrin via a heterogeneous and efficient NiFe2O4@SiO2–SO3H nanoparticle-catalysed, ultrasonic irradiation-assisted, eco-friendly protocol. The NiFe2O4@SiO2–SO3H nanopowder has been synthesized and thoroughly characterized by FTIR, powdered XRD, FESEM, HRTEM, EDX and N2 adsorption analysis. The most desirable agenda of our methodology is to evolve an eco-friendly green protocol with minimum reaction time and easy reaction condition. A new and efficient catalyst, broad scope in substrate variation, very high yield percentages, use of green solvent and very short reaction time are the crucial advantages of our methodology.
CONFLICT OF INTEREST
There are no conflicts to declare.
Open Research
DATA AVAILABILITY STATEMENT
Research data are not shared.
Supporting Information
| Filename | Description |
|---|---|
| aoc6426-sup-0001-Supporting Information 2 (Tiff file of 4l).tiffTIFF image, 1.6 MB |
Data S1. Supporting information |
| aoc6426-sup-0002-Revised Supporting Information 1.docxWord 2007 document , 3.8 MB |
Data S2. Supporting information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
REFERENCES
- 1D. Astruc, F. Lu, J. R. Aranzaes, Angew. Chem., Int. Ed. 2005, 44, 7852.
- 2a) B. M. Reddy, A. Khan, Catal. Rev.: Sci. Eng. 2005, 47, 257; b) M. B. Gawande, V. D. B. Bonifácio, R. S. Varma, I. D. Nogueira, N. Bundaleski, C. A. A. Ghumman, O. M. N. D. Teodorod, P. S. Branco, Green Chem. 2013, 15, 1226.
- 3E. Rafiee, S. Eavania, Green Chem. 2011, 13, 2116.
- 4S. Minakata, M. Komatsu, Chem. Rev. 2009, 109, 711.
- 5A. Dandia, V. Parewa, A. K. Jain, K. S. Rathore, Green Chem. 2011, 13, 2135.
- 6M. Zhang, J. Lu, J. N. Zhang, Z. H. Zhang, Catal. Commun. 2016, 78, 26.
- 7R. S. Turtelli, G. V. Duong, J. Magn. Magn. Mater. 2008, 320, 339.
- 8A. Goldman, Modern Ferrite Technology, Van Nostrand Reinhold, New York 1990 35.
- 9M. B. Gawande, Y. Monga, R. Zboril, R. K. Sharma, Coord. Chem. Rev. 2015, 288, 118.
- 10a) S. Ray, A. Bhaumik, M. Pramanik, C. Mukhopadhyay, RSC Adv. 2014, 4, 15441; b) S. Ray, P. Das, A. Bhaumik, A. Dutta, C. Mukhopadhyay, Appl. Catal., a 2013, 458, 183; c) L. A. Joyce, S. H. Shabbir, E. V. Anslyn, Chem. Soc. Rev. 2010, 39, 3621; d) M. North, R. Pasquale, C. Young, Green Chem. 2010, 12, 1514.
- 11a) S. Basu, T. Ghosh, S. Maity, P. Ghosh, C. Mukhopadhyay, ChemistrySelect 2019, 4, 5763; b) A. R. Kiasat, J. Davarpanah, J. Mol. Catal. A: Chem. 2013, 373, 46.
- 12C. S. Gill, B. A. Price, C. W. Jones, J. Catal. 2007, 251, 145.
- 13S. Kralj, D. Makovec, S. Campelj, M. Drofenik, J. Magn. Magn. Mater. 2010, 322, 1847.
- 14B. Zeynizadeh, S. Rahmani, E. Eghbali, Polyhedron 2019, 168, 57.
- 15a) S. Ray, P. Manna, C. Mukhopadhyay, Ultrason. Sonochem. 2015, 22, 22; b) S. Mandal, S. Hazra, S. Sarkar, C. Bodhak, A. Pramanik, Appl. Organometal. Chem. 2019, 33, e4702.
- 16a) M. J. James, N. D. Grant, P. O'Brien, R. J. K. Taylor, W. P. Unsworth, Org. Lett. 2016, 18, 6256; b) Z. Zhang, F. Xiao, B. Huang, J. Hu, B. Fu, Z. Zhang, Org. Lett. 2016, 18, 908.
- 17K. J. Duffy, R. C. Haltiwanger, A. J. Freyer, F. Li, J. I. Luengo, H. Y. Cheng, J. ChemSoc. Perkin Trans. 2002, 2, 181.
- 18P. Diana, A. Martorana, P. Barraja, J. Med. Chem. 2008, 51, 2387.
- 19K. Torisu, K. Kobayashi, M. Iwahashi, Y. Nakai, T. Onoda, T. Nagase, I. Sugimoto, Y. Okada, R. Matsumoto, F. Nanbu, S. Ohuchida, H. Nakai, M. Toda, Bioorg. Med. Chem. 2004, 12, 5361.
- 20J. R. Burke, M. A. Pattoli, K. R. Gregor, J. Biol. Chem. 2003, 278, 1450.
- 21A. M. Akondi, S. Mekala, M. L. Kantam, R. Trivedi, R. Chowhan, A. Das, New J. Chem. 2017, 41, 873.
- 22Y. Ohtake, A. Naito, H. Hasegawa, K. Kawano, D. Morizono, M. Taniguchi, Y. Tanaka, H. Matsukawa, K. Naito, T. Oguma, Y. Ezure, Y. Tsuriya, Bioorg. Med. Chem. 1999, 7, 1247.
- 23M. S. Khan, M. A. Munawar, M. Ashraf, Bioorg. Med. Chem. 2014, 22, 1195.
- 24U. Sehlstedt, P. Aich, J. Bergman, E. I. Vallberg, B. Norden, A. Graslund, J. Mol. Biol. 1998, 278, 31.
- 25C. H. Tseng, Y. R. Chen, C. C. Tzeng, Eur. J. Med. Chem. 2016, 108, 258.
- 26A. Gazit, H. App, G. McMahon, J. Chen, A. Levitzki, F. D. Bohmer, J. Med. Chem. 1996, 39, 2170.
- 27J. Ameri Rad, A. Jarrahpour, C. C. Ersanlı, Z. Atioglu, M. Akkurtd, E. Turos, Tetrahedron 2017, 73, 1135.
- 28C. O. Kappe, Bioorg. Med. Chem. Lett. 2000, 10, 49.
- 29E. K. Dziadulewicz, T. J. Ritchie, A. Hallett, C. R. Snell, S. Y. Ko, R. Wrigglesworth, G. A. Hughes, A. R. Dunstan, G. C. Bloomfield, G. S. Drake, M. C. Brown, W. Lee, G. M. Burgess, C. Davis, M. Yaqoob, M. N. Perkins, E. A. Campbell, A. J. Davis, H. P. Rang, J. Med. Chem. 2000, 43, 769.
- 30J. S. Ren, J. Diprose, J. Warren, R. M. Esnouf, L. E. Bird, S. Ikemizu, M. Slater, J. Milton, J. Balzarini, D. I. Stuart, D. K. Stammers, J. Biol. Chem. 2000, 275, 5633.
- 31A. V. Ivachtchenko, Y. A. Ivanenkov, O. D. Mitkin, A. A. Vorobiev, I. V. Kuznetsova, N. A. Shevkun, A. G. Koryakova, R. N. Karapetian, A. S. Trifelenkov, D. V. Kravchenko, M. S. Veselov, N. V. Chufarova, Eur. J. Med. Chem. 2015, 99, 51.
- 32L. Skalova, M. Nobilis, B. Szotakova, E. Kondrova, M. Savlik, V. Wosol, G. L. Pichard, E. Maser, Biochem. Pharmacol. 2002, 64, 297.
- 33T. Ishihara, H. Kakuta, H. Moritani, T. Ugawa, S. Sakamoto, S. I. Tsukamoto, I. Yanagisawa, Bioorg. Med. Chem. 2003, 11, 2403.
- 34a) R. H. Friend, R. W. Gymer, A. B. Holmes, J. H. Burroughes, R. N. Marks, C. Taliani, D. D. C. Bradley, D. A. Dos Santos, J. L. Bredas, M. Logdlund, W. R. Salaneck, Nature 1999, 397, 6715; b) S. R. Marder, B. Kippelen, A. K. Y. Jen, N. Peyghammbarian, Nature 1997, 388, 845; c) M. Fukuda, K. Savada, K. Yoshino, J. Poly. Sci. A. Poly Chem. 1993, 31, 2465; d) J. Teetsov, M. A. Fox, J. Mater. Chem. 1999, 9, 2117; e) M. Grell, D. D. C. Bradley, M. Inbasekaran, E. P. Woo, Adv. Mater. 1997, 9, 798; f) J. Jo, C. Chi, S. Hoeger, G. Wegner, D. Y. Yoon, Chem. – Eur. J. 2004, 10, 2681.
- 35V. Kumari, K. Dey, S. Giri, A. Bhaumik, RSC Adv. 2016, 6, 45701.
- 36S. Basu, U. Kayal, S. Maity, P. Ghosh, A. Bhaumik, C. Mukhopadhyay, ChemistrySelect 2018, 3, 12755.
- 37a) S. Dutta, A. K. Patra, S. De, A. Bhaumik, B. Saha, ACSAppl. Mater.Interfaces. 2012, 4, 1560; b) A. K. Patra, S. K. Das, A. Bhaumik, J. Mater. Chem. 2011, 21, 3925.
- 38H. Naeimi, Z. S. Nazifi, J. Nanopart. Res. 2013, 15, 2026.
