Notes: Preparation of Acetals and Ketals from Enol Esters

Hirsh, D. H.; Hoaglin, R. I.; Kubler, D. G.

doi:10.1021/jo01101a628

Cited by 9 publications

(3 citation statements)

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“…The authors noticed that the methodology was improved by mechanochemistry, i.e. by milling the mercuric acetate in ethanol [232] . More recently, Chapman et al.…”

Section: Tandem Reactionsmentioning

confidence: 99%

“…by milling the mercuric acetate in ethanol. [232] More recently, Chapman et al noticed the simultaneous formation of acetylated and acetalizated products during the reaction between iPAc and 1-phenyl-1,2-ethanediol catalyzed by In(ClO 4 ) 3 (Scheme 71, top). [233] Mukherjee et al reported that molecular iodine catalyzes acetalization and acetylation of reducing sugars and sugar glycosides with stoichiometric amounts of enol acetates under solvent-free conditions (14 examples; 62-91 % yields; Scheme 71, bottom).…”

Section: Tandem Reactionsmentioning

confidence: 99%

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Isopropenyl Esters (iPEs) in Green Organic Synthesis

Rigo

Masters

Maschmeyer

et al. 2022

Chemistry A European J

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The need for greener compounds able to replace conventional ones with similar reactivity is crucial for the development of sustainable chemistry. Isopropenyl esters (iPEs) represent one eco-friendly alternative to acyl halides and anhydrides. This review provides a comprehensive overview of the preparation methodologies and reported synthetic applications of iPEs and, in particular, of isopropenyl acetate (iPAc). Intriguingly, the presence of a C=C double bond adjacent to the ester functionality makes iPEs appealing in different chemoselective organic synthesis transformations. For instance, the acyl moiety is suitable for transesterification reactions in presence of different heteroatom-based nucleo-philes (CÀ , OÀ , NÀ , SÀ , SeÀ ); these reactions are irreversible thanks to the formation of acetone, obtained upon keto-enol tautomerization of the prop-1-en-2-ol (isopropenyl) leaving group. Similarly, the unsaturation contained in the isopropenyl synthon could be selectively exploited in organic synthesis for electrophilic and/or radical additions as well as in metal-catalyzed cross-coupling reactions. To conclude, iPEs recently found major interest in the direct modification of biomass (i.e. lignin or cellulose) and in the implementation of tandem reactions of esterification-acetalization by exploiting the co-formation of acetone during the reaction.

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“…The authors noticed that the methodology was improved by mechanochemistry, i.e. by milling the mercuric acetate in ethanol [232] . More recently, Chapman et al.…”

Section: Tandem Reactionsmentioning

confidence: 99%

Section: Tandem Reactionsmentioning

confidence: 99%

Isopropenyl Esters (iPEs) in Green Organic Synthesis

Rigo

Masters

Maschmeyer

et al. 2022

Chemistry A European J

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“…Quinazoline derivatives are of special importance because of their versatile biological & pharmacological activities [18][19][20] , especially anti-inflammatory [21][22][23] , anticonvulsant 24 ,hypnotic 25 , anthemintic 26 , hypo-tensive 27 , antibacterial 28 agents etc. In the present work, s-alkylated derivatives of thio-quinazolinone were obtained using Ethyl chloroacetate via a solvent-free microwave-assisted method.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and QSAR Study of Some HDL Cholesterol Increasing Quinazolinone Derivatives

Deshmukh

Dhongade

2004

Journal of Chemistry

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We describe here an easy and efficient method to obtain s-alkylated derivatives of thio-quinazolinone using different alkylating agents via a solvent-free microwave-assisted method. The alkylated thio quinazolinones were further sequentially condensed with hydrazine hydrate and different aromatic aldehydes to get the hydrazones, which were studied for QSAR. The synthesized compounds were subjected to a prediction of biological activities. A software application (PASS) was used for this purpose. The relationship between structure and different biological activities was studied and the different derivatives were recommended for the screening of some specific activities like anti-tuberculosic, anti-mycobacterial and HDL cholesterol increasing activities.

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The reaction of vinyl ethers with acridine

Takano

Ishihara

Saito

et al. 1996

Journal of Heterocyclic Chem

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The reaction of vinyl ethers with acridine gives new acridine derivatives in the presence of an organic ammonium salt and alcohol. An organic ammonium salt such as acridinium chloride affect this reaction. All of the addition products were obtained as dihydroacridinyl derivatives. Moreover, in the reaction of ketene silyl acetal with acridine, the addition products were also obtained as the dihydroacridine derivatives.

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Notes: Preparation of Acetals and Ketals from Enol Esters

Abstract: NOTES 1083 as benzoic acid, and that the acidic strength of the second hydrogen of II is about the same as that of the phenol. These results are given in Table II.

Cited by 9 publications

References 0 publications

Isopropenyl Esters (iPEs) in Green Organic Synthesis

Isopropenyl Esters (iPEs) in Green Organic Synthesis

Synthesis and QSAR Study of Some HDL Cholesterol Increasing Quinazolinone Derivatives

The reaction of vinyl ethers with acridine

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