Analysis by GC-MS of an Aza-Michael Reaction Catalyzed by CALB on an Orbital Shaker and under Microwave Irradiation
biocatalysis; amines; aza-michael addition; enones; imines
Abstract
In this study, aza-Michael reactions between 1-phenylmethanamine and α,β-unsaturated cyclohexenones were investigated, using lipase from Candida antarctica. The reactions were performed in various organic solvents (CH 2 Cl 2 , hexane, MeOH, toluene, THF) under mild conditions, with orbital shaking and microwave irradiation. The reactions showed good results in the presence of CALB, yielding the Michael adducts and imines. The reaction products were analyzed by GC-MS and in some cases it was found that the reverse aza-Michael reaction had occurred.
Downloads
- Article PDF
- TEI XML Kaleidoscope (download in zip)* (Beta by AI)
- Lens* NISO JATS XML (Beta by AI)
- HTML Kaleidoscope* (Beta by AI)
- DBK XML Kaleidoscope (download in zip)* (Beta by AI)
- LaTeX pdf Kaleidoscope* (Beta by AI)
- EPUB Kaleidoscope* (Beta by AI)
- MD Kaleidoscope* (Beta by AI)
- FO Kaleidoscope* (Beta by AI)
- BIB Kaleidoscope* (Beta by AI)
- LaTeX Kaleidoscope* (Beta by AI)
How to Cite
References
Vicente Gotor‐fernández, Eduardo Busto, Vicente Gotor (2006) Candida antarctica lipase B: An ideal biocatalyst for the preparation of nitrogenated organic compounds Adv Synth Catal. 348(7-8), 797-812. https://doi.org/10.1002/adsc.200606057
J. Yadav, B. Reddy, A. Basak, A. Narsaiah (2003) S.; Reddy, B V S.; Basak, A K.; Narsaiah, A V Aza-Michael reactions in ionic liquids A facile synthesis of α-amino compounds Chem Lett. 32(11), 988-989. https://doi.org/10.1246/cl.2003.988
Yuhong Zhang, Yanguang Wang, Huaxing Zhang, Leifang Liu, Hailiang Xu (2005) RuCl3 in poly(ethylene glycol): A highly efficient and recyclable catalyst for the conjugate addition of nitrogen and sulfur nucleophiles Synthesis. 2005(13), 2129-2136. https://doi.org/10.1055/s-2005-870010
Rajiv Trivedi, P. Lalitha, Sarabindu Roy (2008) Vanadyl(IV) acetate: An efficient, reusable heterogenous catalyst for aza- Michael reaction under solvent-free conditions Synth Commun. 38(20), 3556-3566. https://doi.org/10.1080/00397910802164740
Alexander Rulev (2011) Y Aza-Michael reaction: achievements and prospects Russian Chem Rev. 80(3), 197-218. https://doi.org/10.1070/rc2011v080n03abeh004162
Kishor Dhake, Pawan Tambade, Rekha Singhal, Bhalchandra Bhanage (2010) P.; Tambade, P J.; Singhal, R S.; Bhanage, B M Promiscuous Candida antarctica lipase B-catalyzed synthesis of β-amino esters via aza-Michael addition of amines to acrylates Tetrahedron Lett. 51(33), 4455-4458. https://doi.org/10.1016/j.tetlet.2010.06.089
Anguo Ying, Ming Zheng, Haidan Xu, Fangli Qiu, Changhua Ge (2011) Guanidine-based task-specific ionic liquids as catalysts for aza-Michael addition under solvent-free conditions Res Chem Intermed. 37(8), 883-890. https://doi.org/10.1007/s11164-011-0296-9
Surya Singh, T. Kumar, M. Chandrasekharam, L. Giribabu, P. Reddy (2009) P.; Kumar, T V.; Chandrasekharam, M.; Giribabu, L.; Reddy, P Y Microwave-assisted, rapid, solvent-free aza-Michael reaction by perchloric acid impregnated on silica gel Synth Commun. 39(22), 3982-3989. https://doi.org/10.1080/00397910902883579
Tai-Bao Wei, Mao-Tang Hua, Hai-Xiong Shi, Yong Liu, You-Ming Zhang (2010) Aza-Michael addition of acrylonitrile with 2- aryloxymethylbenzimidazole derivatives under microwave irradiation J Chem Research. 34(8), 452-454. https://doi.org/10.3184/030823410x12798039968476
E. Dockal (1985) A simple and efficient synthesis of thymoquinone and methyl pbenzoquinone. 15, 1033-1036.
M. Uliana (2008) Oxidation of mono-phenols to parabenzoquinones: a comparative study. 19, 1484-1489.
Sandra Ribeiro, Cristiano Raminelli, André Porto (2013) S.; Raminelli, C.; Porto, A L M Enzymatic resolution by CALB of organofluorine compounds under conventional condition and microwave irradiation J Fluorine Chem. 154, 53-59. https://doi.org/10.1016/j.jfluchem.2013.06.014
Sandra Ribeiro, Julieta Oliveira, André Porto (2012) S.; De Oliveira, J R.; Porto, A L M Lipase-catalyzed kinetic resolution of (±)- mandelonitrile under conventional condition and microwave irradiation J Braz Chem Soc. 23(7), 1395-1399. https://doi.org/10.1590/s0103-50532012000700025
G. Melgar (2010) First stereocontrolled acetylation of a hydroxypropargylpiperidone by lipase CALB. 21(18), 2271-2274. https://doi.org/10.1016/j.tetasy.2010.07.024
H. Ferraz (2007) Enzymatic resolution of α-tetralols by CALB-catalyzed acetylation. 18, 1070-1076.
R. Souza (2009) Michael additions of primary and secondary amines to acrylonitrile catalyzed by lipases. 50.
Priego, J.; Ortíz-Nava, C.; Carrillo-Morales, A. M.; López-Munguía (2009) Escalate, J.; Castillo, E Solvent engineering: an effective tool to direct chemoselectivity in a lipase-catalyzed Michael addition. 65(2), 536-539. https://doi.org/10.1016/j.tet.2008.10.103
Prabhakar Bachu, Jennifer Gibson, Jonathan Sperry, Margaret Brimble (2007) The influence of microwave irradiation on lipasecatalyzed kinetic resolution of racemic secondary alcohols. 18(13), 1618-1624. https://doi.org/10.1016/j.tetasy.2007.06.035
Lenilson Rocha, Isac Rosset, Rodrigo Luiz, Cristiano Raminelli, André Porto (2010) Kinetic resolution of iodophenylethanols by Candida antarctica lipase and their application for the synthesis of chiral biphenyl compounds. 21(8), 926-929. https://doi.org/10.1016/j.tetasy.2010.05.008
Brian Mather, Kalpana Viswanathan, Kevin Miller, Timothy Long (2006) D.; Viswanathan, K.; Miller, K M.; Long, T E Michael addition reactions in macromolecular design for emerging technologies Prog Polym Sci. 31(5), 487-531. https://doi.org/10.1016/j.progpolymsci.2006.03.001
A. Hoz, L. de, A. Días-Ortiz, M. Gómez, J. Mayoral, A. Moreno, A. Sánchez-Migallón, E. Vazquez (2001) de L.; Días-Ortiz, A.; Gómez, M V.; Mayoral, J A.; Moreno, A.; Sánchez-Migallón, A M.; Vazquez, E Preparation of α- and β-substitutend alanine derivatives by α-amidoalkylation or Michael addition reactions under heterogeneous catalysis assisted by microwave irradiation. 57, 5421-5428.
WSS: Spectral data were obtained from Wiley Subscription Services, Inc. (US).
Yuhong Zhang, Yanguang Wang, Huaxing Zhang, Leifang Liu, Hailiang Xu (2005) RuCl3 in Poly(ethylene glycol): A Highly Efficient and Recyclable Catalyst for the Conjugate Addition of Nitrogen and Sulfur Nucleophiles. 2005(13), 2129-2136. https://doi.org/10.1055/s-2005-870010
Yu, D.; Wang, Z.; Chen, P.; Jin, L.; Vheng, Y.; Zhou, S. J.; Cao (2007) Microwave-assisted resolution of (R,S)-2- octanol by enzymatic transesferification. 48(1-2), 51-57. https://doi.org/10.1016/j.molcatb.2007.06.009
Rubén Montalvo-González, Armando Ariza-Castolo (2003) Molecular structure of di-aryl-aldimines by multinuclear magnetic resonance and X-ray diffraction J Mol Structure. 655(3), 375-389. https://doi.org/10.1016/s0022-2860(03)00279-5
Published
2014-01-21
Issue
Section
License
Copyright (c) 2014 Authors and Global Journals Private Limited

This work is licensed under a Creative Commons Attribution 4.0 International License.