Microwave-assisted Synthesis of Some New N, N`-Bis-[(2-hydroxy- napthalene-1-yl) Substituted Phenyl-methyl] 4,4`-diaminodiphenyl- Sulphone

Authors: Dalia A. Abdul¹ & Faiq H.S. Hussain^2
1Department of Chemistry, College of Science, University of Sulaimani, Sulaimani, Iraq
²TIU, Research Center, Tishk International University, Erbil, Iraq

Abstract:  An efficient and easy approach to N,N`-Bis-[(2-hydroxy-napthalene-1-yl) substituted phenylmethyl] 4,4`-diamine diphenyl sulphone derivatives is presented in this study. The products can be obtained both through the traditional method and via the microwave assisted protocol from the condensation of 4,4`-diamine diphenyl sulphone, benzaldehydes derivatives and β-naphthol. The characterization of the newly provided compounds elucidated by spectral methods: FT-IR, ¹H-NMR, ¹³C-NMR, and Mass spectral data. Finally, the bis-Bestti bases have been screened for antimicrobial and antifungal activities.

Keywords: Bis-Betti Base, 2-Naphthol, Microwave, One-Pot Reaction, Aromatic Aldehydes

Download the PDF Documentfrom here .

doi: 10.23918/eajse.v4i4p48

References

Betti, M. (1900). On the addition of benzyl amine to naphthol. Gazz. Chim. Ital, 30, 301-309.

Betti, M. (1941). β-Naphthol phenylaminomethane. Org Synth Coll, 1, 381-3.

Cardellicchio, C., Capozzi, M. A. M., & Naso, F. (2010). The Betti base: The awakening of a sleeping beauty. Tetrahedron: Asymmetry, 21(5), 507-517.

Deepam, A., & Viswanadhan, J. (2017). Green protocols for the one-pot synthesis of vanillin based aminoalkyl and Amidoalkyl Naphthols and their antibacterial activity. Oriental Journal of Chemistry, 33(3), 1354-1365.

Dindulkar, S. D., Puranik, V. G., & Jeong, Y. T. (2012). Supported copper triflate as an efficient catalytic system for the synthesis of highly functionalized 2-naphthol Mannich bases under solvent free condition. Tetrahedron Letters, 53(33), 4376-4380.

Gao, H., Sun, J., & Yan, C. G. (2015). Synthesis of new type of Betti bases via three-component reaction of β-naphthol, cyclic amines and isatins. Chinese Chemical Letters, 26(3), 353-356.

Gawande, M. B., Shelke, S. N., Zboril, R., & Varma, R. S. (2014). Microwave-assisted chemistry: synthetic applications for rapid assembly of nanomaterials and organics. Accounts of Chemical Research, 47(4), 1338-1348.

Heydenreich, M., Koch, A., Klod, S., Szatmári, I., Fülöp, F., & Kleinpeter, E. (2006). Synthesis and conformational analysis of naphth [1′, 2′: 5, 6][1, 3] oxazino [3, 2-c][1, 3] benzoxazine and naphth [1′, 2′: 5, 6][1, 3] oxazino [3, 4-c][1, 3] benzoxazine derivatives. Tetrahedron, 62(48), 11081-11089.

Jha, A., Paul, N. K., Trikha, S., & Cameron, T. S. (2006). Novel synthesis of 2-naphthol Mannich bases and their NMR behaviour. Canadian Journal of Chemistry, 84(6), 843-853.

Kappe, C. O. (2006). The use of microwave irradiation in organic synthesis. From laboratory curiosity to standard practice in twenty years. CHIMIA International Journal for Chemistry, 60(6), 308-312.

Karmakar, B., & Banerji, J. (2011). A competent pot and atom-efficient synthesis of Betti bases over nanocrystalline MgO involving a modified Mannich type reaction. Tetrahedron Letters, 52(38), 4957-4960.

Kumar, A., Gupta, M. K., & Kumar, M. (2010). Non-ionic surfactant catalyzed synthesis of Betti base in water. Tetrahedron Letters, 51(12), 1582-1584.

Mou, J., Gao, G., Chen, C., Liu, J., Gao, J., Liu, Y., & Pei, D. (2017). Highly efficient one-pot three-component Betti reaction in water using reverse zinc oxide micelles as a recoverable and reusable catalyst. RSC Advances, 7(23), 13868-13875.

Salamone, M., Amorati, R., Menichetti, S., Viglianisi, C., & Bietti, M. (2014). Structural and medium effects on the reactions of the cumyloxyl radical with intramolecular hydrogen bonded phenols. The interplay between hydrogen-bonding and acid-base interactions on the hydrogen atom transfer reactivity and selectivity. The Journal of Organic Chemistry, 79(13), 6196-6205.

Shen, A. Y., Tsai, C. T., & Chen, C. L. (1999). Synthesis and cardiovascular evaluation of N-substituted 1-aminomethyl-2-naphthols. European Journal of Medicinal Chemistry, 34(10), 877-882.

Szatmári, I., & Fülöp, F. (2013). Syntheses, transformations and applications of aminonaphthol derivatives prepared via modified Mannich reactions. Tetrahedron, 69, 1255-1278.