Simple protic ionic liquid [Et3NH][HSO4] as a proficient catalyst for facile synthesis of biscoumarins

Patil, Sandip K.; Awale, Deepak V.; Vadiyar, Madagonda M.; Patil, S. A.; Bhise, Sagar C.; Kolekar, Sanjay S.

doi:10.1007/s11164-017-2932-5

Cited by 27 publications

(11 citation statements)

References 55 publications

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“…Synthesized ionic liquids were characterized by the 1 H NMR, IR spectroscopy, and high resolution‐mass spectrometry (HRMS). The presence of a broad resonance signal at δ H 13.01 ( 1a ), 15.59 ( 1b ), 13.0 ( 1c ), 10.96 ( 1d ), 14.9 ( 1e ), 9.40 ( 2a ), 9.05 ( 2b ), 9.28 ( 2c ), 9.00 ( 2d ), and 8.94 ( 2e ) ppm in the 1 H NMR spectrum confirms the formation of N−H bond (Supporting Information) . It is further supported by IR spectroscopy which exhibits a broad absorption band at 2990–3035 cm −1 attributed to N−H bond stretching vibrations…”

Section: Resultssupporting

confidence: 55%

Economically Viable and Efficient Catalysts for Esterification and Cross Aldol Condensation Reactions under Mild Conditions

Bano

Jain²,

Sarkar

et al. 2020

ChemistrySelect

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Brønsted acidic ionic liquids (BAILs) have been used as catalyst and solvent in organic synthesis, due to their negligible volatility, remarkable solubility, good catalytic activity, and easily structurally tunable properties. In the present study, we have investigated the catalytic efficiency of economically viable ionic liquids bearing different cations pyridinium ([PyH] + and triethylammonium [TEAH] + ) for the esterification of aromatic acid with various aliphatic alcohols and crossed aldol condensation of aromatic aldehydes with cyclohexanone under ambient condition. We also examined the effect of various process parameters on the yield of aromatic esters and α,α'-bis (arylidene)cycloalkanones.

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Section: Resultssupporting

confidence: 55%

Economically Viable and Efficient Catalysts for Esterification and Cross Aldol Condensation Reactions under Mild Conditions

Bano

Jain²,

Sarkar

et al. 2020

ChemistrySelect

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“…Patil et al . developed a condensation reaction of 4HC and the aryl aldehydes to produce biscoumarins in the vicinity of EtOH as a solvent and PIL (protic ionic liquids) as a catalyst ( Scheme : Method 4) .…”

Section: General Synthesis Of Biscoumarinmentioning

confidence: 99%

An Insight View on Synthetic Protocol, Mechanistic and Biological Aspects of Biscoumarin Derivatives

2019

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Biscoumarin has emerged as one of the most unique and valuable moiety in the field of synthetic as well as in medicinal chemistry. This moiety has been examined for the designing of potent derivatives and hybrids with other moieties and substituents exhibiting a myriad of medicinal properties. These far‐flung characteristics enthralled the researchers to discover various methods for the synthesis of biscoumarin nucleus and its derivatives from 4‐hydroxycoumarin and varieties of aldehydes using different types of catalysts to improve the selectivity, purity and yield of the products. Moreover, liberal scope is available for this structural unit which needs to be explored by chemists for the advancement of new potential drug candidates. This article summarizes the current eco‐benign pathways for the synthetic strategies of biscoumarins under various reaction conditions viz. solid supported catalyst, ionic liquid, nanoparticles, Lewis acid, heteropolyacids, nanocomposites etc.

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“…The ionic liquid [Et 3 NH][HSO 4 ] has been used extensively in various organic transformations, for the synthesis of thiazolidine and oxazolidine derivatives, [ 41 ] quinolone derivatives, [ 42 ] α‐aminophosphonates, [ 43 ] 5‐arylidine‐rohdanine conjugates, [ 44 ] synthesis of coumarin, [ 45 ] and biscoumarins. [ 46 ]…”

Section: Introductionmentioning

confidence: 99%

[Et₃NH][HSO₄] catalyzed solvent‐free synthesis of new 1,2,3‐triazolidene‐indolinone derivatives

Siddiqui

Nagargoje

Raza

et al. 2022

Journal of Heterocyclic Chem

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A series of new 1,2,3‐triazolidene‐indolinone derivatives (17a‐j) were designed and synthesized via [Et3NH] [HSO4] catalyzed solvent‐free approach. The synthesis strongly relied on Knoevenagel condensation of 1,4‐disubstituted 1,2,3‐triazolyl aldehydes (15a‐j) and oxindole (5). The solvent‐free approach and Brønsted acidity of [Et3NH] [HSO4] ionic liquid increased the rate of reaction and provided the corresponding 1,2,3‐triazolidene‐indolinone derivatives (17a‐j) in excellent yields. The reusability of ionic liquid is also established with persistent effective yields up to four cycles. These novel 1,2,3‐triazolidene‐indolinone derivatives may exhibit potential biological response due to the presence of potent moieties and presence of triazolidene‐exocyclic double bond.

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Simple protic ionic liquid [Et3NH][HSO4] as a proficient catalyst for facile synthesis of biscoumarins

Cited by 27 publications

References 55 publications

Economically Viable and Efficient Catalysts for Esterification and Cross Aldol Condensation Reactions under Mild Conditions

Economically Viable and Efficient Catalysts for Esterification and Cross Aldol Condensation Reactions under Mild Conditions

An Insight View on Synthetic Protocol, Mechanistic and Biological Aspects of Biscoumarin Derivatives

[Et₃NH][HSO₄] catalyzed solvent‐free synthesis of new 1,2,3‐triazolidene‐indolinone derivatives

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Simple protic ionic liquid [Et3NH][HSO4] as a proficient catalyst for facile synthesis of biscoumarins

Cited by 27 publications

References 55 publications

Economically Viable and Efficient Catalysts for Esterification and Cross Aldol Condensation Reactions under Mild Conditions

Economically Viable and Efficient Catalysts for Esterification and Cross Aldol Condensation Reactions under Mild Conditions

An Insight View on Synthetic Protocol, Mechanistic and Biological Aspects of Biscoumarin Derivatives

[Et3NH][HSO4] catalyzed solvent‐free synthesis of new 1,2,3‐triazolidene‐indolinone derivatives

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Product

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[Et₃NH][HSO₄] catalyzed solvent‐free synthesis of new 1,2,3‐triazolidene‐indolinone derivatives