Novel Phenolic 1-aryl-3-arylamino-1-propanones: Synthesis and Characterization

Open access


A small collection of 1-aryl-3-arylamino-1-propanones having a phenolic moiety in their structure has been obtained by the replacement of the tertiary amino group in ketonic Mannich bases with (hetero)aromatic amines. The installment of the phenolic moiety took place either through the N-alkylation of 4-aminophenol with ketonic Mannich base hydrochlorides, or via amine exchange in ketonic Mannich bases derived from either 2′-hydroxyacetophenone or 4′-hydroxyacetophenone.

1. Tilak, B. D.; Ravindranathan, T.; Subbaswami, K.N. Synthesis of quinoline derivatives involving hydride transfer. Tetrahedron Lett. 1966, 1959-1963.

2. Gogte, V. N.; Salama, M. A.; Tilak, B. D. Synthesis of nitrogen heterocyclics — VI: Stereochemistry of hydride transfer in acid-catalysed disproportionation of 3,4-disubstituted 1,2-dihydroquinolines. Tetrahedron 1970, 26, 173-181.

3. Andreani, F.; Andrisano, R.; Salvadori, G.; Tramontini, M. Reactivity of Mannich bases. Part XIV. Synthesis of phenylbenzoquinoline and styrylbenzoquinoline derivatives and their photoreactivity. J. Chem. Soc. [C] 1971, 1007-1013.

4. Andreani, F.; Andrisano, R.; Tramontini, M. Researches on the reactivity of Mannich bases. Part VIII. Synthesis of N-methyl(vinylaryl)quinolinium salts and their photosensitivity. J. Heterocycl. Chem. 1967, 4, 171-177.

5. Ardashev, B. I.; Kagan, E. S.; Mezheritskii, V. V.; Sidorova, T. F. Synthesis of lepidine and its derivatives from aromatic amines and quaternary salts of Mannich bases. Chem. Heterocycl. Compds. 1967, 2, 177-179.

6. Roth, H. J.; Schumann, E. Mannichbasen als Zwischenstufen bei Chinolinsynthesen. Arch. Pharm. (Weinheim) 1970, 303, 268-274.

7. Afsah, E. M.; Keshk, E. M.; Abdel-Rahman, A.-R. H.; Jomah, N. F. Mannich bases as synthetic intermediates: Convenient synthesis of functionalized 1,2,4-triazepines, 1,4-diazepines and 1,5-diazocines. Z. Naturforsch. B 2011, 66, 577-584.

8. Zhou, C.; Wu, G.; Feng, Y.; Li, Q.; Su, H.; Mais, D.E.; Zhu, Y.; Li, N.; Deng, Y.; Yang, D.; Wang, M.-W. Discovery and biological characterization of a novel series of androgen receptor modulators. Br. J. Pharmacol. 2008, 154, 440-450.

9. Du, Y.; Li, Q.; Xiong, B.; Hui, X.; Wang, X.; Feng, Y.; Meng, T.; Hu, D.; Zhang, D.; Wang, M.; Shen, J. Aromatic β-amino-ketone derivatives as novel selective non-steroidal progesterone receptor antagonists. Bioorg. Med. Chem. 2010, 18, 4255-4268.

10. Damljanović, I.; Stevanović, D.; Pejović, A.; Vukićević, M.; Novaković, S. B.; Bogdanović, G. A.; Mihajlov-Krstev, T.; Radulović, N.; Vukićević, R. D. Antibacterial 3-(arylamino)-1-ferrocenylpropan-1-ones: synthesis, spectral, electrochemical and structural characterization. J. Organomet. Chem. 2011, 696, 3703-3713.

11. Liu, D.; Yu, W.; Li, J.; Pang, C.; Zhao, L. Novel 2-(E)-substituted benzylidene-6-(N-substituted aminomethyl)cyclohexanones and cyclohexanols as analgesic and anti-inflammatory agents. Med. Chem. Res. 2013, 22, 3779-3786.

12. Tang, G. X.; Yan, J. F.; Fan, L.; Xu, J.; Song, X. L.; Jiang, L.; Luo, L. F.; Yang, D. C. Synthesis of novel β-amino ketones containing a p-aminobenzoic acid moiety and evaluation of their antidiabetic activities. Sci. China: Chem. 2013, 56, 490-504.

13. Kenchappa, R.; Bodke, Y. D.; Peethambar, S. K.; Telkar, S.; Bhovi, V. K. Synthesis of β-amino carbonyl derivatives of coumarin and benzofuran and evaluation of their biological activity. Med. Chem. Res. 2013, 22, 4787-4797.

14. Roman, G.; Comaniţă, E.; Comaniţă, B.; Drăghici, D. Synthesis and reactivity of some Mannich bases. V. Arylamine N-alkylation with Mannich bases derived from 2-hydroxy-5-methylacetophenone. J. Serb. Chem. Soc. 1998, 63, 931-939.

15. Roman, G.; Comaniţă, E.; Comaniţă, B.; Nanu, D. Synthesis and reactivity of some Mannich bases. VI. New arylamine Mannich bases derived from 2-hydroxy-5-methylacetophenone. Turk. J. Chem. 2000, 24, 67-72.

16. Keshavarzipour, F.; Tavakol, H. Deep eutectic solvent as a recyclable catalyst for three-component synthesis of β-amino carbonyls. Catal. Lett. 2015, 145, 1062-1066.

17. Abedini-Torghabeh, J.; Eshghi, H.; Bakavoli, M.; Rahimizadeh, M. PPh3-catalyzed Mannich reaction. A facile one-pot synthesis of β-amino carbonyl compounds under solvent-free conditions at room temperature. Res. Chem. Intermed. 2015, 41, 3649-3658.

18. Liu, D.; Zhang, J.; Zhang, C.; Kou, X. One-pot synthesis of β-amino carbonyl compounds catalyzed silica supported phenylphosphinic acid. Green Process. Synth. 2015, 4, 11-15.

19. Craig, J. C.; M. Moyle, M.; Johnson, L. F. Amine exchange reactions. Mannich bases from aromatic amines. J. Org. Chem. 1964, 29, 410-415.

20. Roman, G.; Mareş, M.; Năstasă, V. A novel antifungal agent with broad spectrum: 1-(4-Biphenylyl)-3-(1H-imidazol-1-yl)-1-propanone. Arch. Pharm. (Weinheim) 2013, 346, 110-118.

21. Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. NMR chemical shifts of common laboratory solvents as trace impurities. J. Org. Chem. 1997, 62, 7512-7515.

22. Gewald, K.; Schinke, E.; Böttcher, H. Heterocyclen aus CH-aciden Nitrilen, VIII. 2-Amino-thiophene aus methylenaktiven Nitrilen, Carbonyl-verbindungen und Schwefel. Chem. Ber. 1966, 99, 94-100.

23. Lehmann, F.; Pilotti, Å; Luthman, K. Efficient large scale microwave assisted Mannich reactions using substituted acetophenones. Mol. Divers. 2003, 7, 145-152.

24. Sielemann, D.; Keuper, R.; Risch, N. Efficient preparation of substituted 5,6,7,8-tetrahydroquinolines and octahydroacridine derivatives. J. Prakt. Chem. 1999, 341, 487-491.

25. Kuliev, A.M.; Guseinov, M. S.; Sardarova, S. A.; Iskenderova, T. Yu. Alkylation by Mannich bases. Synthesis and study of morpholine and piperazine derivatives of hydroxypropiophenones. J. Org. Chem. USSR 1972, 1315-1318.

26. Roman, G. Synthesis of novel 3-substituted-1-(2′-hydroxyphenyl) propan-1-ones. Rev. Chim. (Bucharest) 2016, 67, 1692-1696.

Acta Chemica Iasi

The Journal of "Alexandru Ioan Cuza" University from Iasi

Journal Information


All Time Past Year Past 30 Days
Abstract Views 0 0 0
Full Text Views 330 181 7
PDF Downloads 165 122 5