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L-proline-catalyzed Knoevenagel reaction promoted by choline chloride-based deep eutectic solvents

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Abstract

Knoevenagel condensation of acetylacetone and aromatic aldehyde catalyzed by L-proline in the choline chloride-based deep eutectic solvents was achieved. High yields are up to 96.6%. Mild reaction conditions, enhanced rates, improved yields, recyclability of deep eutectic solvents containing L-proline, and reagents’ reactivity which is different from that in standard organic solvents are the remarkable features observed in deep eutectic solvents. The deep eutectic solvents containing catalyst was recycled in four subsequent runs with no decrease in activity.

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References

  1. Hayashi Y, Tsuboi W, Shoji M, Suzuki N (2003) Application of high pressure induced by water-freezing to the direct catalytic asymmetric three-component List–Barbas–Mannich reaction. J Am Chem Soc 125(37):11208–11209. https://doi.org/10.1021/ja0372513

    Article  Google Scholar 

  2. Hirose M, Sugisaki S, Suga K, Umakoshi H (2019) Detection of L-proline-catalyzed Michael addition reaction in model biomembrane. J Chem 2019:1–8. https://doi.org/10.1155/2019/4926435

    Article  Google Scholar 

  3. Hayashi Y, Urushima T, Tsuboi W, Mitsuru S (2007) L-proline-catalyzed enantioselective one-pot cross-Mannich reaction of aldehydes. Nat Protoc 2(1):113–118. https://doi.org/10.1038/nprot.2006.472

    Article  Google Scholar 

  4. Al-Momani LA, Lorbach V, Detry J, Geilenkirchen P, Mller M (2016) β- and σ-amino acids (2,3- and 3,4-trans-CHA) as catalysts in Knoevenagel condensation and asymmetric aldol reactions. Arkivoc 6:172–183. https://doi.org/10.24820/ark.5550190.p009.854

    Article  Google Scholar 

  5. Bakkolla MG, Taduri AK, Bhoomireddy RD (2018) A facile synthesis of novel (Z )-ethyl-3-(5-substituted-1-alkyl/aryl-1H -indol-3-yl)-2-(1H -tetrazol-5-yl)acrylate. J Heterocycl Chem 00:00. https://doi.org/10.1002/jhet.3375

    Article  Google Scholar 

  6. Groth U, de Meijere A, Beifuss U, Belzner J, Tietze LF, von Kiedrowski G et al (1991) Comprehensive organic synthesis. Selectivity, strategy and efficiency in modern organic chemistry, vol. 1–9. Reihenherausgeber: B. M. Trost) Pergamon Press, Oxford. https://doi.org/10.1002/ange.19931050746

  7. Zhang H, Han M, Chen T, Xu L, Yu L (2017) Poly(N-isopropylacrylamide-co-l-proline)-catalyzed Claisen-Schmidt and Knoevenagel condensations: unexpected enhanced catalytic activity of the polymer catalyst. RSC Adv 7(76):48214–48221. https://doi.org/10.1039/c7ra09412d

    Article  Google Scholar 

  8. Tasqeeruddin S, Asiri Y, Alsherhri JA (2020) An efficient and green microwave-assisted synthesis of quinoline derivatives via Knoevengal condensation. Lett Org Chem 17(2):157–163. https://doi.org/10.2174/1570178616666190618153721

    Article  Google Scholar 

  9. Lei ZG, Chen BH, Koo YM (2017) Douglas RM (2019) Introduction: ionic liquids. Chem Rev 117(10):6633–6635. https://doi.org/10.1021/acs.chemrev.7b00246

    Article  Google Scholar 

  10. Wang Y, Shang Z, Wu T, Fan J, Chen X (2006) Synthetic and theoretical study on proline-catalyzed Knoevenagel condensation in ionic liquid. J Mol Catal A: Chem 253(1–2):212–221. https://doi.org/10.1016/j.molcata.2006.03.035

    Article  Google Scholar 

  11. Syed T, Yahya IA (2020) An environmentally benign, green, and efficient ionic liquid catalyzed synthesis of Quinoline derivatives via Knoevenagel condensation. J Heterocycl Chem 57(1):1–516. https://doi.org/10.1002/jhet.3754

    Article  Google Scholar 

  12. Abbott AP, Capper G, Davies DL, Munro HL, Rasheed RK, Tambyrajah V (2001) Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains. Chem Commun 19:2010–2011. https://doi.org/10.1039/B106357J

    Article  Google Scholar 

  13. Smith L, Abbott AP, Ryder KS (2014) Deep eutectic solvents (DESs) and their applications. Chem Rev 114(21):11060–11082. https://doi.org/10.1021/cr300162p

    Article  Google Scholar 

  14. Zhang M, Liu YH, Shang ZR, Hu HC, Zhang ZH (2017) Supported molybdenum on graphene oxide/Fe3O4: an efficient, magnetically separable catalyst for one-pot construction of spiro-oxindole dihydropyridines in deep eutectic solvent under microwave irradiation. Catal Commun 88:39–44. https://doi.org/10.1016/j.catcom.2016.09.028

    Article  Google Scholar 

  15. Liu P, Hao J-W, Mo L-P, Zhang Z-H (2015) Recent advances in the application of deep eutectic solvents as sustainable media as well as catalysts in organic reactions. RSC Adv 5:48675–48704. https://doi.org/10.1039/C5RA05746A

    Article  Google Scholar 

  16. Gao G, Wang P, Liu P, Zhang W-H, Mo L-P, Zhang Z-H (2018) Deep eutectic solvent catalyzed one-pot synthesis of 4,7-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carbonitriles. Chin J Org Chem 38:846–854. https://doi.org/10.6023/cjoc201711014

    Article  Google Scholar 

  17. Martínez R, Berbegal L, Guillena G, Ramón DJ (2016) Bio-renewable enantioselective aldol reaction in natural deep eutectic solvents. Green Chem 18:1724–1730. https://doi.org/10.1039/c5gc02526e

    Article  Google Scholar 

  18. Brenna D, Massolo E, Puglisi A, Sergio Rossi, Celentano G, Benaglia M, Capriati V (2016) Towards the development of continuous, organocatalytic, and stereoselective reactions in deep eutectic solvents. Beilstein J Org Chem 12:2620–2626. https://doi.org/10.3762/bjoc.12.258

    Article  Google Scholar 

  19. Abbott AP, Boothby D, Capper G, Davies DL, Rasheed RK (2004) Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids. J Am Chem Soc 126(29):9142–9147. https://doi.org/10.1021/ja048266j

    Article  Google Scholar 

  20. Durand E, Lecomte J, Villeneuve P (2013) Deep eutectic solvents: Synthesis, application, and focus on lipase-catalyzed reactions. Eur J Lipid Sci Technol 115(4):379–385. https://doi.org/10.1002/ejlt.201200416

    Article  Google Scholar 

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Acknowledgements

We gratefully acknowledge the Natural Science Foundation of Guangdong Province(Grant No. 2018A030307022) and the Special Innovation Projects of Common Universities in Guangdong Province (Grant No. 2018KTSCX126).

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Authors and Affiliations

  1. Laboratory of Marine Green Fine Chemicals, School of Chemistry and Chemical Engineering, LingNan Normal University, Zhanjiang, 524048, China

    Yun Wang, Qiao-Xia Yao, Jia-Rui He, Zhi-Hui Liang, Xiang Li, Hong Cheng & Li-Ling Li

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  1. Yun Wang
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  2. Qiao-Xia Yao
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  3. Jia-Rui He
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  4. Zhi-Hui Liang
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Correspondence to Yun Wang.

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Wang, Y., Yao, QX., He, JR. et al. L-proline-catalyzed Knoevenagel reaction promoted by choline chloride-based deep eutectic solvents. Biomass Conv. Bioref. 12 (Suppl 1), 87–93 (2022). https://doi.org/10.1007/s13399-021-01747-9

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