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Collect. Czech. Chem. Commun. 2005, 70, 1943-1952
https://doi.org/10.1135/cccc20051943

Efficient Synthesis of β-Aminoacrylates and β-Enaminones Catalyzed by Zn(OAc)2·2H2O

Ramandeep Kaur Vohra, Jean-Luc Renaud* and Christian Bruneau*

Institut de Chimie, UMR 6509, Organométalliques et Catalyse, Université de Rennes 1, Campus de Beaulieu-35042 Rennes Cedex, France

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  • Sayad Rayene, Bouzina Abdeslem, Bouone Yousra Ouafa, Beldjezzia Dounia, Djemel Abdelhak, Ibrahim-Ouali Malika, Aouf Nour-Eddine, Aouf Zineb: Zinc acetate-catalyzed, green and efficient synthesis of xanthene derivatives under ultrasound irradiation: X-ray crystallographic analysis and in silico study. RSC Adv. 2024, 14, 24585. <https://doi.org/10.1039/D4RA04135F>
  • Alam Mohammed Mujahid, Varala Ravi, Seema Vittal: Zinc Acetate in Organic Synthesis and Catalysis: A Review. MROC 2024, 21, 555. <https://doi.org/10.2174/1570193X20666230507213511>
  • Santos Felipe B., Pezzini Emily, Cargnelutti Roberta, Penteado Filipe, Schumacher Ricardo F.: Synthesis of Two Isomers of pyrido/benzo[b][1,4]selenazines: A Selective Catalyst‐Dependent Formation of C−N and C‐Se Bonds. Adv Synth Catal 2023, 365, 4286. <https://doi.org/10.1002/adsc.202301003>
  • Dutta Sriparna, Kumar Prashant, Sharma Shivani, Yadav Sneha, Priyanka, Dixit Ranjana, Srivastava Anju, Sharma Rakesh Kumar: A versatile core–shell hetero-nanostructure catalysed chemo-selective synthesis of β-enamino carbonyl compounds. RSC Sustain. 2023, 1, 975. <https://doi.org/10.1039/D3SU00073G>
  • Wang Yeming, Zhang Chaoqun, Li Shizhe, Liu Lihui, Feng Xiaodong: Recent Advances in Transition Metal Catalyzed Synthesis of β‐Enaminones and β‐Enaminoesters. ChemistrySelect 2022, 7. <https://doi.org/10.1002/slct.202103345>
  • Redjemia Rayenne, Bouzina Abdeslem, Bouone Yousra Ouafa, Mansouri Achraf, Bahadi Rania, Berredjem Malika: Copper (I) bromide (CuBr): a highly efficient catalyst for the synthesis of β-enaminone derivatives using ultrasound irradiation under solvent-free conditions. Res Chem Intermed 2022, 48, 4947. <https://doi.org/10.1007/s11164-022-04853-z>
  • Mousavi Seyyed Rasul, Sereshti Hassan, Rashidi Nodeh Hamid, Foroumadi Alireza: A novel and reusable magnetic nanocatalyst developed based on graphene oxide incorporated strontium nanoparticles for the facial synthesis of β‐enamino ketones under solvent‐free conditions. Applied Organom Chemis 2019, 33. <https://doi.org/10.1002/aoc.4644>
  • Prakasham A. P., Gangwar Manoj Kumar, Ghosh Prasenjit: β‐Enaminone Synthesis from 1,3‐Dicarbonyl Compounds and Aliphatic and Aromatic Amines Catalyzed by Iron Complexes of Fused Bicyclic Imidazo[1,5‐a]pyridine Derived N‐Heterocyclic Carbenes. Eur J Inorg Chem 2019, 2019, 295. <https://doi.org/10.1002/ejic.201800906>
  • Eidi Esmaiel, Kassaee Mohamad Z., Cummings Peter T.: β-Enaminones over recyclable nano-CoFe2O4: a highly efficient solvent-free green protocol. Res Chem Intermed 2018, 44, 5787. <https://doi.org/10.1007/s11164-018-3454-5>
  • Dutta Gargi, Jana Ajay Kumar, Natarajan Srinivasan: Assembling Porphyrins into Extended Network Structures by Employing Aromatic Dicarboxylates: Synthesis, Metal Exchange, and Heterogeneous Catalytic Studies. Chemistry A European J 2017, 23, 8932. <https://doi.org/10.1002/chem.201700985>
  • Prabakaran Kaliyan, Sivakumar Matam, Perumal Muthu Seenivasa: A Simple, Efficient Green Protocol for the Synthesis of β‐Enaminone and Enamino Ester Derivatives by Using Onion Extract as Green Catalyst. ChemistrySelect 2017, 2, 2363. <https://doi.org/10.1002/slct.201601515>
  • Wodtke Felipe, Xavier Fernando R., Mendes Samuel R., de Oliveira Alfredo R.M., Gariani Rogério A.: A simple protocol for the preparation of β-enamino ketones catalyzed by NbOPO4 under solvent free conditions. Tetrahedron Letters 2017, 58, 231. <https://doi.org/10.1016/j.tetlet.2016.12.019>
  • Deng Dian, Xiao Lang, Chung Ill-Min, Kim Ick Soo, Gopiraman Mayakrishnan: Industrial-Quality Graphene Oxide Switched Highly Efficient Metal- and Solvent-Free Synthesis of β-Ketoenamines under Feasible Conditions. ACS Sustainable Chem. Eng. 2017, 5, 1253. <https://doi.org/10.1021/acssuschemeng.6b02766>
  • Rout Lipeeka, Kumar Aniket, Dhaka Rajendra S., Dash Priyabrat: Bimetallic Ag–Cu alloy nanoparticles as a highly active catalyst for the enamination of 1,3-dicarbonyl compounds. RSC Adv. 2016, 6, 49923. <https://doi.org/10.1039/C6RA04569C>
  • De Rosa Michael, Arnold David, Hartline Douglas, Truong Linda, Verner Roman, Wang Tianwei, Westin Christian: Effect of Bronsted Acids and Bases, and Lewis Acid (Sn2+) on the Regiochemistry of the Reaction of Amines with Trifluoromethyl-β-diketones: Reaction of 3-Aminopyrrole to Selectively Produce Regioisomeric 1H-Pyrrolo[3,2-b]pyridines. J. Org. Chem. 2015, 80, 12288. <https://doi.org/10.1021/acs.joc.5b02192>
  • Huo Hongfei, Li Xinzhe, Zhou Xingchun, Jiao Lixin, Zhao Shiling, Zhang Le, Li Wenzhu, Li Shuwen, Li Rong: Fabrication of Ag/γ-Fe2O3@TiO2 hollow magnetic core–shell nanospheres as highly efficient catalysts for the synthesis of β-enaminones. RSC Adv. 2015, 5, 73612. <https://doi.org/10.1039/C5RA14878B>
  • Feng Cheng-Liang, Chu Ning-Ning, Zhang Shu-Guang, Cai Jin, Chen Jun-Qing, Hu Hua-You, Ji Min: Solvent-free synthesis of β-enamino ketones and esters catalysed by recyclable iron(III) triflate. Chem. Pap. 2014, 68, 1097. <https://doi.org/10.2478/s11696-014-0544-8>
  • Liu Yu-Heng, Wang Ping, Cheng Gui-Tian: A general and efficient method for synthesis of enaminones and enamino esters catalyzed by NbCl5 under solvent-free conditions. Monatsh Chem 2013, 144, 191. <https://doi.org/10.1007/s00706-012-0783-8>
  • Brož Břetislav, Padělková Zdeňka, Bertolasi Valerio, Šimůnek Petr: A simple new hydrazine-free synthesis of methyl 1,4,5-trisubstituted 1H-pyrazole-3-carboxylates. Monatsh Chem 2013, 144, 1013. <https://doi.org/10.1007/s00706-013-0962-2>
  • Sun Jian, Dong Zhengping, Li Ping, Zhang Fengwei, Wei Shuoyun, Shi Zhiqiang, Li Rong: Ag nanoparticles in hollow magnetic mesoporous spheres: A highly efficient and magnetically separable catalyst for synthesis of β-enaminones. Materials Chemistry and Physics 2013, 140, 1. <https://doi.org/10.1016/j.matchemphys.2013.03.030>
  • Tayyari Sayyed Faramarz, Ghafari Maliheh, Jamialahmadi Mina, Chahkandi Behzad, Patrick Brian O., Wang Yan Alexander: Vibrational assignment and crystal structure of 3-amino-1-phenyl-2-buten-1-one. Journal of Molecular Structure 2013, 1045, 20. <https://doi.org/10.1016/j.molstruc.2013.04.029>
  • Laskar Rajibul A., Begum Naznin A., Hedayetullah Mir Mohammad, Ali Shahzad, Khan Abu T.: Vanadium(IV) acetylacetonate catalyzed stereoselective synthesis of β-enaminoesters and β-enaminones. Tetrahedron Letters 2013, 54, 436. <https://doi.org/10.1016/j.tetlet.2012.11.051>
  • Zhao Ying, Deng Dong-Sheng, Ma Lu-Fang, Ji Bao-Ming, Wang Li-Ya: A new copper-based metal–organic framework as a promising heterogeneous catalyst for chemo- and regio-selective enamination of β-ketoesters. Chem. Commun. 2013, 49, 10299. <https://doi.org/10.1039/c3cc45310c>
  • Zohreh N., Alizadeh A., Babaki M., Kornienko Alexander: One‐Pot Solvent‐Free Three‐Component Synthesis of Conjugated Enaminones Containing Three Alkyl Carboxylate Groups. Journal of Chemistry 2013, 2013. <https://doi.org/10.1155/2013/473968>
  • Feng Chengliang, Zhang Shuguang, Cai Jin, Chen Junqing, Hu Huayou, Ji Min: Zinc Triflate Catalysed Synthesis of β-Enamino Ketones(Esters) under Solvent-Free Conditions. Journal of Chemical Research 2013, 37, 626. <https://doi.org/10.3184/174751913X13787959859506>
  • Martins Marcos A.P., Rossatto Marcelo, Prola Liziê D.T., Pizzuti Lucas, Moreira Dayse N., Campos Patrick T., Frizzo Clarissa P., Zanatta Nilo, Bonacorso Helio G.: Ultrasound promoted the synthesis of N-propargylic β-enaminones. Ultrasonics Sonochemistry 2012, 19, 227. <https://doi.org/10.1016/j.ultsonch.2011.06.011>
  • Samantaray Manoja K., Dash Chandrakanta, Shaikh Mobin M., Pang Keliang, Butcher Ray J., Ghosh Prasenjit: Gold(III) N-Heterocyclic Carbene Complexes Mediated Synthesis of β-Enaminones From 1,3-Dicarbonyl Compounds and Aliphatic Amines. Inorg. Chem. 2011, 50, 1840. <https://doi.org/10.1021/ic102268n>
  • Liu Ju‐Yan, Cao Gai‐E, Xu Wei, Cao Jie, Wang Wei‐Lu: Ni(OAc)2: a highly efficient catalyst for the synthesis of enaminone and enamino ester derivatives under solvent‐free conditions. Applied Organom Chemis 2010, 24, 685. <https://doi.org/10.1002/aoc.1667>
  • Harrad Mohamed Anoir, Outtouch Rachid, Ait Ali Mustapha, Firdoussi Larbi El, Karim Abdallah, Roucoux Alain: Ca(CF3COO)2: An efficient Lewis acid catalyst for chemo- and regio-selective enamination of β-dicarbonyl compounds. Catalysis Communications 2010, 11, 442. <https://doi.org/10.1016/j.catcom.2009.11.019>
  • Moreau Julie, Hubert Claudie, Batany Jessika, Toupet Loic, Roisnel Thierry, Hurvois Jean-Pierre, Renaud Jean-Luc: Metal-Free Brønsted Acid Catalyzed Formal [3 + 3] Annulation. Straightforward Synthesis of Dihydro-2H-Chromenones, Pyranones, and Tetrahydroquinolinones. J. Org. Chem. 2009, 74, 8963. <https://doi.org/10.1021/jo901238y>
  • Mohammadizadeh Mohammad R., Hasaninejad A., Bahramzadeh M., Khanjarlou Z. Sardari: P2O5/SiO2 as a New, Efficient, and Reusable Catalyst for Preparation of β-Enaminones Under Solvent-Free Conditions. Synthetic Communications 2009, 39, 1152. <https://doi.org/10.1080/00397910802513052>
  • Li Geng-Chen: Simple and efficient synthesis of 3-aminopropenones and 3-aminopropenoates catalyzed by copper(II) nitrate trihydrate under solvent-free conditions. Monatsh Chem 2008, 139, 789. <https://doi.org/10.1007/s00706-007-0832-x>
  • Martins Marcos A.P., Frizzo Clarissa P., Moreira Dayse N., Rosa Fernanda A., Marzari Mara R.B., Zanatta Nilo, Bonacorso Helio G.: Synthesis of β-enaminones by ionic liquid catalysis: A one-pot condensation under solvent-free conditions. Catalysis Communications 2008, 9, 1375. <https://doi.org/10.1016/j.catcom.2007.11.037>
  • Zhang Zhan-Hui, Li Tong-Shuang, Li Jian-Jiong: Synthesis of enaminones and enamino esters catalysed by ZrOCl2· 8H2O. Catalysis Communications 2007, 8, 1615. <https://doi.org/10.1016/j.catcom.2007.01.015>
  • Epifano Francesco, Genovese Salvatore, Curini Massimo: Ytterbium triflate catalyzed synthesis of β-enaminones. Tetrahetron Lett 2007, 48, 2717. <https://doi.org/10.1016/j.tetlet.2007.02.064>
  • Li Geng-Chen: Phosphotungstic Acid Catalysed Synthesis of β-Enamino Compounds under Solvent-Free Conditions. Journal of Chemical Research 2007, 2007, 696. <https://doi.org/10.3184/030823407X273488>
  • Vohra Ramandeep Kaur, Bruneau Christian, Renaud Jean‐Luc: Lewis Acid‐Catalyzed Sequential Transformations: Straightforward Preparation of Functional Dihydropyridines. Adv Synth Catal 2006, 348, 2571. <https://doi.org/10.1002/adsc.200600343>
  • Vohra Ramandeep Kaur, Renaud Jean‐Luc, Bruneau Christian: Efficient Synthesis of β‐Aminoacrylates and β‐Enaminones Catalyzed by Zn(OAc)2×2H2O. ChemInform 2006, 37. <https://doi.org/10.1002/chin.200620046>