Bi(NO3)3•5H2O-catalyzed Mannich Reaction: A Potent Catalyst for Synthesis of β-Aminocarbonyl Compounds

Abstract

Biologically active compounds containing nitrogen, natural molecules and drugs are important for organic synthesis. Mannich reaction is one of the most common methods used for the synthesis of these compounds. Bi(NO₃)₃ was used as an efficient catalyst for the one-pot three-component Mannich reactions of ketones with different aromatic amines and aromatic aldehydes at room temperature. It is a good method to prepare β-amino carbonyl compounds in excellent yield. The high efficiency using simple starting materials and a catalytic amount of a reusable catalyst is especially noteworthy.

Keywords

• Mannich reaction,One-pot synthesis,Bismuth (III) nitrate

References

1. 1. Ai T, Han J, Chen ZX, Li G. Chiral N‐Phosphonyl Imine Chemistry: Asymmetric Synthesis of α‐Alkyl β‐Amino Ketones by Reacting Phosphonyl Imines with Ketone‐Derived Enolates. Chem Biol Drug Des. 2009, 73, 203-208.
2. 2. Zhiani R, Nishaburi AT, Abedi F, Moradi M. A rapid and green method for synthesis of β-amino ketones (Mannich reaction) using an acid catalyst nano- SiO2. Indian J. Fund. Appl. Life Sci. 2014, 4: 779-784.
3. 3. Srivastava BK, Kapadnis PB, Pandya P, Lohray VB. Novel Mannich ketones of oxazolidinones as antibacterial agents. Eur. J. Med. Chem. 2004, 39: 989-992.
4. 4. Lutz Z, Orban K, Bona A, Mark L, Maasz G, Prokai L, Seress L, Lorand T. Mannich Ketones as Possible Antimycobacterial Agents, Arch. Pharm. Chem. Life Sci. 2017, 350: e1700102.
5. 5. Hollosy F, Lorand T, Orfi L, Eros D, Keri G, Idei M. Relationship between lipophilicity and antitumor activity of molecule library of Mannich ketones determined by high-performance liquid chromatography, clogP calculation and cytotoxicity test. J. Chromatogr. B. 2001, 768: 361-368.
6. 6. Loranda T, Kocsis B, Sohar P, Nagy G, Kispal G, Krane HG, Schmitt H, Weckert E. Synthesis and antibacterial study of unsaturated Mannich ketones. Eur. J. Med. Chem. 2001, 36: 705-717.
7. 7. Filho JFA, Lemos BC, Souza AS, Pinheiro S, Greco SJ. Multicomponent Mannich reactions: General aspects, methodologies and applications, Tetrahedron. 2017, 73: 6977-7004.
8. 8. Yi WB and Cai C. Mannich-type reactions of aromatic aldehydes, anilines, and methyl ketones in fluorous biphase systems created by rare earth (III) perfluorooctane sulfonates catalysts in fluorous media. J. Fluorine Chem. 2006, 127: 1515-1521.

9. 9. Wang R, Li BG, Huang TK, Shi L, Lu XX. NbCl5-Catalyzed one-pot Mannich-type reaction: three component synthesis of β-amino carbonyl compounds. Tetrahedron Lett. 2007, 48: 2071-2073.
10. 10. Fujisawa H, Takahashi E, Mukaiyama T. Lewis base catalyzed Mannich-type reactions between trimethylsilyl enol ethers and aldimines. Chemistry. 2006, 12: 5082-5093.
11. 11. Rajput JK, Kaur G. Bi(NO3)3·5H2O: An Efficient and Green Catalyst for Synthesis of 1,5-Benzodiazepines and β-Amino Carbonyl Compounds. Asian J. Chem. 2013, 25: 6545-6549.
12. 12. Ravikumar Naik TR, Bhojya Naik HS, Raghavendra M, Bindu PJ, Mahadevan KM. Synthesis of novel 1,5-benzothiazepine[7,6-b]-1, 8-naphthyridines under microwave irradiation via Mannich condensation. J. Sulfur Chem. 2007, 28: 589-595.
13. 13. Sheik Mansoor S, Aswin K, Logaiya K, Sudhan SPN. An efficient synthesis of β-amino ketone compounds through one-pot three-component Mannich-type reactions using bismuth nitrate as catalyst. J. Saudi Chem. Soc. 2015, 19: 379-386.
14. 14. Min W, Yan L, Zhigou S. Aluminium nitrate as an efficient and reusable catalyst for the three components one-pot Mannich reaction: Synthesis of -amino carbonyl compounds Indian. J. Chem., Sect. B: Org. Chem. Including Med. Chem. 2010, 49: 1653-1656.
15. 15. El-Sayed Mansour ME, El-Sadany SK, Kassem AA, Maksoud H. Aminolysis of para-substituted benzalacetophenones., J. Chem. And Eng. Data. 1989, 34: 368-370.
16. 16. Hua L, Hang-yao Z, Hua-wu. Bismuth(III) chloride-catalyzed one-pot Mannich reaction: three-component synthesis of β-amino carbonyl compounds. Tetrahedron Lett. 2009, 50:6858-6860.
17. 17. Abdghasem D, Afsaneh TN, Niloofar TH. Carbon-based Solid Acid Catalyzed One-pot Mannich Reaction: A Facile Synthesis of β-Amino Carbonyl Compounds. Bull. Korean Chem. Soc. 2011, 32: 635-638.
18. 18. Hai-Tang L, Yu-Ru K, Hong-Yun N, Li-Ming Y. Sulfamic Acid as a Cost‐Effective and Recyclable Catalyst for β‐Amino Carbonyl Compounds Synthesis. J. Chin. Chem. Soc. 2009, 56: 186-195.
19. 19. Kozlov NS, Kiseleva SA, Buzykin BI. Reaktionen Aromatischer Azomethine Mit Benzoylaceton. Zh. Org. Khim. 1974, 10: 1487.
20. 20. Kozlov NS, Kiseleva SA, Buzykin B. Catalytic reaction of azomethines with benzoylactone. Tr. Perm. Sel.-Khoz. Inst. 1971, 79: 13.
21. 21. Neelakantan L, Hartung WH. α-Aminoalkanesulfonic Acids. J. Org. Chem. 1959, 24: 1943-1948.
22. 22. Wu M, Jing H, Chang T. Synthesis of β-amino carbonyl compounds via a Mannich reaction catalyzed by Salen Zn complex. Catal. Commun. 2007, 8: 2217-2221.
23. 23. Demirkol O, Akbaşlar D, Giray S, Barış AB. One-Pot Synthesis of Mannich Bases Under Solvent-Free Conditions. Synth. Commun. 2014, 44: 1279-1285.