6‐Diethylphosphonomethyl‐2,2‐dimethyl‐1,3‐dioxen‐4‐one

Boeckman, Robert K.; Perni, Robert B.; Macdonald, James E.; Thomas, Anthony J.

doi:10.1002/0471264180.os066.25

Cited by 3 publications

(3 citation statements)

References 14 publications

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“…30 The synthesis of amides from the reaction of 12 with amines or anilines has typically involved reuxing the substrates in toluene or xylene. 31 A few exceptions include reuxing in THF in the presence of NaOAc for 24 hours, 32 heating in a mixture of biphenyl and diphenyl ether, 33 microwave heating in: THF/DMA, 34 DMF, 35 or in the absence of solvent; 36 or by conventional heating in the presence of the amine, 37 or by the use of dichlorobenzene as solvent. 38 Initially we had prepared acetoacetanilides 15 by reuxing 12 and 14 in toluene.…”

Section: Resultsmentioning

confidence: 99%

An efficient green protocol for the preparation of acetoacetamides and application of the methodology to a one-pot synthesis of Biginelli dihydropyrimidines. Expansion of dihydropyrimidine topological chemical space

2015

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Graphical AbstractA one pot synthesis of Biginelli dihydropyrimidines. The novel use of the aminoacids allows topological diversification of the chemical space. Abstract:The present study describes the preparation of N-aryl-(15) and N-alkyl-(17) acetoacetamides, in good to excellent yields, using both conventional and microwave heating, by reaction of amine derivatives (14 and 16) with 2,2,6-trimethyl-4H-1,3-dioxin-4-one (TMD, 12) in aqueous medium. The acetoacetamides were used

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Section: Resultsmentioning

confidence: 99%

An efficient green protocol for the preparation of acetoacetamides and application of the methodology to a one-pot synthesis of Biginelli dihydropyrimidines. Expansion of dihydropyrimidine topological chemical space

2015

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“…The base-promoted Dieckmann cyclization of glycolyl acetoacetates 4 (Scheme 1) is one of the most synthetically useful methods for the preparation of these 3-acyl derivatives. [8][9][10][11][12][13][14]26,28 The ability of these intermediates to cyclize is highly dependent on the presence of substituents at the α'-position. Thus, while the cyclization of α'-substituted glycolyl acetoacetates is a very easy process, the unsubstituted derivatives require vigorous reaction conditions to success.…”

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confidence: 99%

Synthesis and Chemistry of Tetronic Acids

Tejedor

García‐Tellado

2004

Organic Preparations and Procedures International

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“…An advantage of this method is that it allows Wadsworth-Emmons olefination to be performed subsequent to ring formation, if the final molecule is to be a 3-dienoyl compound. 30 A reported synthesis using an acetoacetyl ester attached to a solid support noted near-quantitative yield, but made no mention of stereoselectivity. 31 Alternative protocols for ring formation require subsequent 3-acylation.…”

Section: Synthetic Methods For Tetramic Acidsmentioning

confidence: 99%

Synthesis and Evaluation of Tetramic Acids as Antimicrobial Agents

Wilson¹

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As bacterial infectious diseases are a major cause of morbity and mortality throughout the world, and many causative organisms are resistant to currently available antibiotics, the motivation for the development of new drugs is readily apparent. A number of natural products exhibiting antimicrobial activity possess a tetramic acid (2,4pyrrolidinedione) functional group. As their antibacterial mechanism of action is different from that of many of the currently available antibiotics, these compounds have potential to serve as a basis for a pharmacophore in synthetic compounds. However, toxicity to eukaryotic cells is frequently a problem with currently known tetramic acids. The purpose of the project, as outlined in the following pages, is to demonstrate a method of synthesis of a small library of compounds containing the tetramic acid ring, and to illustrate their structure-activity relationship as agents both having activity against Grampositive bacteria and possessing low hemolytic activity. Chapter One takes an overview of a number of the different classes of antibiotics available today, with emphasis on their method of action, then covers several naturally occurring tetramic acid compounds with antibiotic activity, and finally methods of synthesis. Chapter Two details the methods used to synthesize and characterize the set of compounds and examines their activity against a set of Gram-positive bacteria, with the purpose of clarifying their structureactivity relationship. v Table of Contents Chapter 1. Introduction.

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6‐Diethylphosphonomethyl‐2,2‐dimethyl‐1,3‐dioxen‐4‐one

Abstract: 6‐Diethylphosphonomethyl‐2,2‐dimethyl‐1,3‐dioxen‐4‐one intermediate: 6‐Chloromethyl‐2,2‐dimethyl‐1,3‐dioxen‐4‐one. product: 6‐diethylphosphonomethyl‐2,2‐dimethyl‐1,3‐dioxen‐4‐one

Cited by 3 publications

References 14 publications

An efficient green protocol for the preparation of acetoacetamides and application of the methodology to a one-pot synthesis of Biginelli dihydropyrimidines. Expansion of dihydropyrimidine topological chemical space

An efficient green protocol for the preparation of acetoacetamides and application of the methodology to a one-pot synthesis of Biginelli dihydropyrimidines. Expansion of dihydropyrimidine topological chemical space

Synthesis and Chemistry of Tetronic Acids

Synthesis and Evaluation of Tetramic Acids as Antimicrobial Agents

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