Abstract
N-Unsubstituted cyclic imides were readily synthesized in deep eutectic solvent (DES) choline chloride (ChCl)/urea from anhydrides with urea. Urea serves as both a DES component and a nitrogen source, which endows the protocol with advantages of smooth reaction, easy separation of products, simple recovery and recycling of ChCl/urea.
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References
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 126:9142–9147. https://doi.org/10.1021/ja048266j
Abbott AP, Capper G, McKenzie KJ, Ryder KS (2006) Voltammetric and impedance studies of the electropolishing of type 316 stainless steel in a choline chloride based ionic liquid. Electrochim Acta 51:4420–4425. https://doi.org/10.1016/j.electacta.2005.12.030
Abdel-Aziz AAM, El-Azab AS, Ghiaty AH, Gratteri P, Supuran CT, Nocentini A (2019) 4-Substituted benzenesulfonamides featuring cyclic imides moieties exhibit potent and isoform-selective carbonic anhydrase II/IX inhibition. Bioorg Chem 83:198–204. https://doi.org/10.1016/j.bioorg.2018.10.037
Alonso DA, Baeza A, Chinchilla R, Guillena G, Pastor IM, Ramón DJ (2016) Deep eutectic solvents: the organic reaction medium of the century. Eur J Org Chem 2016:612–632. https://doi.org/10.1002/ejoc.201501197
Andrade C, Alves LM (2005) Environmentally benign solvents in organic synthesis: current topics. Curr Org Chem 9:195–218. https://doi.org/10.2174/1385272053369178
Azizi N, Batebi E, Bagherpour S, Ghafuri H (2012) Natural deep eutectic salt promoted regioselective reduction of epoxides and carbonyl compounds. RSC Adv 2:2289–2293. https://doi.org/10.1039/C2RA01280D
Benjamin E, Hijji Y (2008) The synthesis of unsubstituted cyclic imides using hydroxylamine under microwave irradiation. Molecules 13:157–169. https://doi.org/10.3390/molecules13010157
Chiriac CI, Nechifor M, Tanasǎ F (2007) Formamide a novel challenging reagent for the direct synthesis of non-N-substituted cyclic imides. Rev Roum Chim 52:883–886. https://doi.org/10.1002/chin.200830081
Crockett GC, Swanson BJ, Anderson DR, Koch TH (1981) A preferred method for imide preparation. Synth Commun 11:447–454. https://doi.org/10.1080/00397918108061876
Dai Y, van Spronsen J, Witkamp G-J, Verpoorte R, Choi YH (2013) Natural deep eutectic solvents as new potential media for green technology. Anal Chim Acta 766:61–68. https://doi.org/10.1016/j.aca.2012.12.019
DeSimone JM (2002) Practical approaches to green solvents. Science 297:799–803. https://doi.org/10.1126/science.1069622
Franks ME, Macpherson GR, Figg WD (2004) Thalidomide. The Lancet 363:1802–1811. https://doi.org/10.1016/S0140-6736(04)16308-3
Gordon AJ, Ehrenkaufer RLE (1971) Chemistry of imides. II. Cyclic imides and some unusual products from some diacid chlorides and lithium nitride. J Org Chem 36:44–45. https://doi.org/10.1021/jo00800a011
Hargreaves MK, Pritchard JG, Dave HR (1970) Cyclic carboxylic monoimides. Chem Rev 70:439–469. https://doi.org/10.1021/cr60266a001
Ilgen F, König B (2009) Organic reactions in low melting mixtures based on carbohydrates and l-carnitine—a comparison. Green Chem 11:848–854. https://doi.org/10.1039/B816551C
Kacprzak K (2003) Rapid and convenient microwave-assisted synthesis of aromatic imides and N-hydroxymethylimides. Synth Commun 33:1499–1507. https://doi.org/10.1081/SCC-120018768
Khandelwal S, Tailor YK, Kumar M (2016) Deep eutectic solvents (DESs) as eco-friendly and sustainable solvent/catalyst systems in organic transformations. J Mol Liq 215:345–386. https://doi.org/10.1016/j.molliq.2015.12.015
Kumar Tailor Y, Khandelwal S, Kumar Jain H, Kumar M (2015) Environmentally benign synthetic protocol for the synthesis of spiroquinazolinones using sustainable and recyclable choline chloride based deep eutectic mixture. Curr Org Synth 12:484–491. https://doi.org/10.2174/157017941204150522190425
Le Z-G, Chen Z-C, Hu Y, Zheng Q-G (2004) Organic reactions in ionic liquids: ionic liquid-promoted efficient synthesis of N-alkyl and N-arylimides. Cheminform 2004:995–998. https://doi.org/10.1055/s-2004-822337
Marvi O (2017) Grinding imidation of anhydrides on smectite clays as recyclable and heterogeneous catalysts under solvent-free conditions. J Chil Chem Soc 62:3501–3504. https://doi.org/10.4067/S0717-97072017000200015
Meng G, Szostak M (2018) N-acyl-glutarimides: privileged scaffolds in amide N–C bond cross-coupling. Eur J Org Chem 20–21:2352–2365. https://doi.org/10.1002/ejoc.201800109
Nikpour F, Kazemi S, Sheikh D (2006) A facile and convenient synthesis of 1H-isoindole-1,3(2H)-diones. Heterocycles 68:1559–1564. https://doi.org/10.3987/COM-06-10762
Osumi Y, Liu C, Szostak M (2017) N-Acylsuccinimides: twist-controlled, acyl-transfer reagents in Suzuki-Miyaura cross-coupling by N–C amide bond activation. Org Biomol Chem 15:8867–8871. https://doi.org/10.1039/c7ob02269g
Paiva A, Craveiro R, Aroso I, Martins M, Reis RL, Duarte ARC (2014) Natural deep eutectic solvents-solvents for the 21st century. ACS Sustain Chem Eng 2:1063–1071. https://doi.org/10.1021/sc500096j
Peng Y, Song G, Qian X (2001) Imidation of cyclic carboxylic anhydrides under microwave irradiation. Synth Commun 31:1927–1931. https://doi.org/10.1081/SCC-100104345
Radošević K, Cvjetko Bubalo M, Gaurina Srček V, Grgas D, Landeka Dragičević T, Radojčić Redovniković I (2015) Evaluation of toxicity and biodegradability of choline chloride based deep eutectic solvents. Ecotoxicol Environ Saf 112:46–53. https://doi.org/10.1016/j.ecoenv.2014.09.034
Rahman A-U, Medrano MA, Mittal OP (1960) Reactions between acids and thiourea: Part I. The formation of amides from acids and thiourea. Recl Trav Chim Pays-Bas 79:188–192. https://doi.org/10.1002/recl.19600790207
Rajawat A, Khandelwal S, Kumar M (2014) Deep eutectic solvent promoted efficient and environmentally benign four-component domino protocol for synthesis of spirooxindoles. RSC Adv 4:5105–5112. https://doi.org/10.1039/c3ra44600j
Rushell E, Tailor YK, Khandewal S, Verma K, Agarwal M, Kumar M (2019) Deep eutectic solvent promoted synthesis of structurally diverse hybrid molecules with privileged heterocyclic substructures. New J Chem 43:12462–12467. https://doi.org/10.1039/c9nj02694k
Shoji A, Kuwahara M, Ozaki H, Sawai H (2007) Modified DNA aptamer that binds the (R)-isomer of a thalidomide derivative with high enantioselectivity. J Am Chem Soc 129:1456–1464. https://doi.org/10.1021/ja067098n
Smith EL, Abbott AP, Ryder KS (2014) Deep eutectic solvents (DESs) and their applications. Chem Rev 114:11060–11082. https://doi.org/10.1021/cr300162p
Tang S, Baker GA, Zhao H (2012) Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications. Chem Soc Rev 41:4030–4066. https://doi.org/10.1039/C2CS15362A
Weaver KD, Kim HJ, Sun J, MacFarlane DR, Elliott GD (2010) Cyto-toxicity and biocompatibility of a family of choline phosphate ionic liquids designed for pharmaceutical applications. Green Chem 12:507–513. https://doi.org/10.1039/B918726J
Wen Q, Chen J-X, Tang Y-L, Wang J, Yang Z (2015) Assessing the toxicity and biodegradability of deep eutectic solvents. Chemosphere 132:63–69. https://doi.org/10.1016/j.chemosphere.2015.02.061
Winter GE, Buckley DL, Paulk J, Roberts JM, Souza A, Dhe-Paganon S, Bradner JE (2015) Phthalimide conjugation as a strategy for in vivo target protein degradation. Science 348:1376. https://doi.org/10.1126/science.aab1433
Xu X, Wang Y, Yang F, Wu C, Wang Z, Ye B, Jiang X, Zhao Q, Li J, Liu Y, Zhang J, Tian G, He Y, Shen J, Jiang H (2018) Synthesis and biological evaluation of a series of multi-target N-substituted cyclic imide derivatives with potential antipsychotic effect. Eur J Med Chem 145:74–85. https://doi.org/10.1016/j.ejmech.2017.12.099
Zhang Q, De Oliveira Vigier K, Royer S, Jérôme F (2012) Deep eutectic solvents: syntheses, properties and applications. Chem Soc Rev 41:7108–7146. https://doi.org/10.1039/C2CS35178A
Zhao B-Y, Xu P, Yang F-X, Wu H, Zong M-H, Lou W-Y (2015) Biocompatible deep eutectic solvents based on choline chloride: characterization and application to the extraction of rutin from sophora japonica. ACS Sustain Chem Eng 3:2746–2755. https://doi.org/10.1021/acssuschemeng.5b00619
Zhu A, Li L, Wang J, Zhuo K (2011) Direct nucleophilic substitution reaction of alcohols mediated by a zinc-based ionic liquid. Green Chem 13:1244–1250. https://doi.org/10.1039/C0GC00763C
Acknowledgements
We acknowledge the financial support from the National Natural Science Foundation of China (Grant No. 21776056).
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Liu, L., Zhang, HY., Yin, G. et al. Synthesis of N-unsubstituted cyclic imides from anhydride with urea in deep eutectic solvent (DES) choline chloride/urea. Chem. Pap. 74, 1351–1357 (2020). https://doi.org/10.1007/s11696-019-00969-6
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DOI: https://doi.org/10.1007/s11696-019-00969-6
Keywords
- N-Unsubstituted cyclic imides
- Deep eutectic solvent
- Choline chloride/urea
- Anhydrides