Synthesis of Benzoin Under Supramolecular Catalysis Involving Cyclodextrins in Water: Application for the Preparation of the Antiepileptic Drug Phenytoin

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 Apr 15

PMID 35424977

Authors

Zhichao Jin

Chunhua Yan

Huimin Chu

Qing Huang

Zhizhong Wang

Affiliations

Soon will be listed here.

Abstract

Among the cyclodextrins screened for the synthesis of 2-hydroxy-1,2-diphenylethanone (benzoin) in water, 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) exhibited the highest yield in the benzoin condensation reactions, and HP-β-CD can be recycled several times with little loss of activity through the addition of fresh VB. As an example of supramolecular catalysis, the methodology was applied to the "green" synthesis of the antiepileptic drug phenytoin through benzoin condensation, oxidation, and cyclization reactions in the presence of HP-β-CD, without the use of any harmful organic solvent. Moreover, the complexation behaviors of HP-β-CD with benzaldehyde and intermediates were studied by UV-vis and 2D-ROESY NMR spectroscopies to reveal the plausible mechanisms of the reactions, and HP-β-CD did not act as a simple phase transfer agent.

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References

Yamabe S, Yamazaki S . Three competitive transition states in the benzoin condensation compared to the clear rate-determining step in the Cannizzaro reaction. Org Biomol Chem. 2009; 7(5):951-61. DOI: 10.1039/b817849f. View

Crini G . Review: a history of cyclodextrins. Chem Rev. 2014; 114(21):10940-75. DOI: 10.1021/cr500081p. View

Dharani S, Barakh Ali S, Afrooz H, Bhattacharya R, Khan M, Rahman Z . Quality and In-Use Stability Comparison of Brand and Generics of Extended-Release Phenytoin Sodium Capsules. J Pharm Sci. 2019; 108(5):1808-1817. DOI: 10.1016/j.xphs.2018.12.022. View

Gonzalez-Gaitano G, Isasi J, Velaz I, Zornoza A . Drug Carrier Systems Based on Cyclodextrin Supramolecular Assemblies and Polymers: Present and Perspectives. Curr Pharm Des. 2016; 23(3):411-432. DOI: 10.2174/1381612823666161118145309. View

Donnelly L, Hardy J, Gorman S, Jones D, Irwin N, McCoy C . Photochemically Controlled Drug Dosing from a Polymeric Scaffold. Pharm Res. 2017; 34(7):1469-1476. PMC: 5445155. DOI: 10.1007/s11095-017-2164-9. View

Lee J, Jang J, Velusamy N, Jung H, Bhuniya S, Kim J . An intramolecular crossed-benzoin reaction based KCN fluorescent probe in aqueous and biological environments. Chem Commun (Camb). 2015; 51(36):7709-12. DOI: 10.1039/c5cc02234g. View

Massey R, Murray J, Collett C, Zhu J, Smith A, ODonoghue A . Kinetic and structure-activity studies of the triazolium ion-catalysed benzoin condensation. Org Biomol Chem. 2020; 19(2):387-393. DOI: 10.1039/d0ob02207a. View

Konnert L, Reneaud B, Marcia de Figueiredo R, Campagne J, Lamaty F, Martinez J . Mechanochemical preparation of hydantoins from amino esters: application to the synthesis of the antiepileptic drug phenytoin. J Org Chem. 2014; 79(21):10132-42. DOI: 10.1021/jo5017629. View

Jansook P, Ogawa N, Loftsson T . Cyclodextrins: structure, physicochemical properties and pharmaceutical applications. Int J Pharm. 2017; 535(1-2):272-284. DOI: 10.1016/j.ijpharm.2017.11.018. View

10.

Kasprzak A, Koszytkowska-Stawinska M, Nowicka A, Buchowicz W, Poplawska M . Supramolecular Interactions between β-Cyclodextrin and the Nucleobase Derivatives of Ferrocene. J Org Chem. 2019; 84(24):15900-15914. DOI: 10.1021/acs.joc.9b02353. View

11.

Sharma N, Baldi A . Exploring versatile applications of cyclodextrins: an overview. Drug Deliv. 2014; 23(3):739-57. DOI: 10.3109/10717544.2014.938839. View

12.

Iwamoto K, Kimura H, Oike M, Sato M . Methylene-bridged bis(benzimidazolium) salt as a highly efficient catalyst for the benzoin reaction in aqueous media. Org Biomol Chem. 2008; 6(5):912-5. DOI: 10.1039/b719430g. View

13.

Bai C, Tian B, Zhao T, Huang Q, Wang Z . Cyclodextrin-Catalyzed Organic Synthesis: Reactions, Mechanisms, and Applications. Molecules. 2017; 22(9). PMC: 6151768. DOI: 10.3390/molecules22091475. View

14.

Rahman Z, Dharani S, Barakh Ali S, Nutan M, Khan M . Effects of Diluents on Physical and Chemical Stability of Phenytoin and Phenytoin Sodium. AAPS PharmSciTech. 2020; 21(3):104. DOI: 10.1208/s12249-020-1639-x. View

15.

White M, Leeper F . Kinetics of the thiazolium ion-catalyzed benzoin condensation. J Org Chem. 2001; 66(15):5124-31. DOI: 10.1021/jo010244h. View