Anion-cation Co-operative Catalysis by Artificial Sweetener Saccharine-based Ionic Liquid for Sustainable Synthesis of 3,4-dihydropyrano[]chromenes, 4,5-dihydropyrano[4,3-]pyran and Tetrahydrobenzo[]pyrans in Aqueous Medium

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 May 13

PMID 35558303

Authors

Himani Sharma

Suman Srivastava

Affiliations

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Abstract

In this study, a saccharine-based ionic liquid [Bmim]Sac has been found to be a sustainable catalyst for the synthesis of 3,4-dihydropyrano[]chromenes, 4,5-dihydropyrano[4,3-]pyran and tetrahydrobenzo[]pyrans scaffolds through Domino Knoevenagel-Michael reaction. The easy recovery of the catalyst and high yield of the products make the protocol attractive, sustainable and economical. A mechanistic hypothesis is discussed using the concept of cooperative catalysis based on the dual (electrophilic/nucleophilic) activation of reactants by [Bmim]Sac. Furthermore, dual hydrogen bonding of saccharinate anions plays an important role in the activation of nucleophiles.

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References

Shaker R . Synthesis and reactions of some new 4H-pyrano[3,2-c]benzopyran-5-one derivatives and their potential biological activities. Pharmazie. 1996; 51(3):148-51. View

Kumar A, Srivastava S, Gupta G, Chaturvedi V, Sinha S, Srivastava R . Natural product inspired diversity oriented synthesis of tetrahydroquinoline scaffolds as antitubercular agent. ACS Comb Sci. 2011; 13(1):65-71. DOI: 10.1021/co100022h. View

Zhang Y, Chen B, Zheng K, Xu M, Zhang L, Lei X . [Chemotherapeutic studies on schistosomiasis. XXV. Derivatives of substituted coumarin-3-carboxylic esters and amides (author's transl)]. Yao Xue Xue Bao. 1982; 17(1):17-22. View

Kumar A, Maurya S, Pratap K, Srivastava S . Betaine mediated synthesis of annulated dihydrofurans from oxobis(methylthio)ketene acetals and N-butyl-N'-methyl ethane-1,2-diamine as precursors via NHC elimination. Chem Commun (Camb). 2016; 52(13):2795-8. DOI: 10.1039/c5cc09509c. View

LAZZERI ADREANI L, Lapi E . [On some new esters of coumarin-3-carboxylic acid wit balsamic and bronchodilator action]. Boll Chim Farm. 1960; 99:583-6. View

Parvulescu V, Hardacre C . Catalysis in ionic liquids. Chem Rev. 2007; 107(6):2615-65. DOI: 10.1021/cr050948h. View

Carter E, Culver S, Fox P, Goode R, Ntai I, Tickell M . Sweet success: Ionic liquids derived from non-nutritive sweeteners. Chem Commun (Camb). 2004; (6):630-1. DOI: 10.1039/b313068a. View

Hu H, Qiu F, Ying A, Yang J, Meng H . An environmentally benign protocol for aqueous synthesis of tetrahydrobenzo[b]pyrans catalyzed by cost-effective ionic liquid. Int J Mol Sci. 2014; 15(4):6897-909. PMC: 4013668. DOI: 10.3390/ijms15046897. View

Lee S . Functionalized imidazolium salts for task-specific ionic liquids and their applications. Chem Commun (Camb). 2006; (10):1049-63. DOI: 10.1039/b514140k. View

10.

Ranu B, Banerjee S . Ionic liquid as catalyst and reaction medium. The dramatic influence of a task-specific ionic liquid, [bmIm]OH, in Michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles. Org Lett. 2005; 7(14):3049-52. DOI: 10.1021/ol051004h. View

11.

Petkovic M, Seddon K, Rebelo L, Pereira C . Ionic liquids: a pathway to environmental acceptability. Chem Soc Rev. 2010; 40(3):1383-403. DOI: 10.1039/c004968a. View

12.

Xu J, Liu B, Wu W, Qian C, Wu Q, Lin X . Basic ionic liquid as catalysis and reaction medium: a novel and green protocol for the Markovnikov addition of N-heterocycles to vinyl esters, using a task-specific ionic liquid, [bmIm]OH. J Org Chem. 2006; 71(10):3991-3. DOI: 10.1021/jo0600914. View

13.

Ren S, Hou Y, Tian S, Chen X, Wu W . What are functional ionic liquids for the absorption of acidic gases?. J Phys Chem B. 2013; 117(8):2482-6. DOI: 10.1021/jp311707e. View

14.

Kumar A, Gupta G, Srivastava S . Synthesis of new class of alkyl azarene pyridinium zwitterions via iodine mediated sp3 C-H bond activation. Org Lett. 2011; 13(24):6366-9. DOI: 10.1021/ol202654j. View

15.

Nockemann P, Thijs B, Driesen K, Janssen C, Van Hecke K, Meervelt L . Choline saccharinate and choline acesulfamate: ionic liquids with low toxicities. J Phys Chem B. 2007; 111(19):5254-63. DOI: 10.1021/jp068446a. View

16.

Kumar A, Gupta G, Srivastava S . Diversity oriented synthesis of pyrrolidines via natural carbohydrate solid acid catalyst. J Comb Chem. 2010; 12(4):458-62. DOI: 10.1021/cc100007a. View

17.

Cole A, Jensen J, Ntai I, Tran K, Weaver K, Forbes D . Novel Brønsted acidic ionic liquids and their use as dual solvent-catalysts. J Am Chem Soc. 2002; 124(21):5962-3. DOI: 10.1021/ja026290w. View