Pfitzinger Reaction Research Articles

Ring-substituted 11-oxo-11H-indeno[1,2-b]quinoline-6-carboxamides with similar patterns of cytotoxicity to the dual topo I/II inhibitor DACA

A series of ring-substituted analogues of the topoisomerase inhibitor 11-oxo-11H-indeno[1,2-b]quinoline-6-carboxamides was prepared and evaluated. The compounds were prepared by Pfitzinger reaction of the appropriate isatin-7-carboxylic acids and 1-indanones, followed by selective thermal decarboxylation of the resulting tetracyclic diacids, subsequent oxidation of the methylene group with alkaline permanganate under carefully controlled conditions, and 1,1'-carbonyldiimidazole-induced amidation. The compounds were evaluated in a panel of cell lines in culture. The largest increases in cytotoxicity (five to tenfold) were shown by 4-substituted analogues, with the 4-Cl derivative having an IC50 of 8nM against the Lewis lung carcinoma.

ChemInform Abstract: Synthetic Use of the Pfitzinger Reaction in Preparation of 2(,3)‐(Di)substituted Derivatives of Quinoline‐4‐carboxylic Acids

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Ethyl (4‐N‐acylaminopyridin‐3‐yl)glyoxylate and 5‐azaisatin as new synthons for a route to various new polyheterocycles

AbstractFrom 4‐N‐protected‐aminopyridines which were functionalized at their 3‐position, 5‐azaisatin and equivalent synthons where obtained. Via the use of the Pfitzinger reaction, these compounds provided an easy route to new and various polyheterocyclic compounds.

Synthesis of carbon C‐14 labelled 2‐phenyl‐4‐alpha‐alkylaminomethyl‐quinolinemethanol: A potential anti‐leishmaniasis agent

AbstractUsing sodium acetate, [1‐14C] as a starting material, a total of seven steps were required to synthesize the title compound. This involved acylation of ortho‐dichlorobenzene to form dichloroacetophenone, [2‐14C] (I). The 2‐phenyl‐4‐quinoline carboxylic acid, [2‐14C] (II) was prepared by the Pfitzinger reaction from (I) and dichloroisatin. Compound II was converted to the acid chloride (III) by reaction with SOCl2 in benzene. Grignard condensation reaction of (III) yielded 4‐quinolylmethylketone, [2‐14C] (IV) which was then converted to the bromomethylketone (V). Compound V was reacted with NaBH4 to form the ethylene oxide (VI). Alkylation of the oxide yielded the title compound (VII). The overall radiochemical yield was 10.1% and the specific activity was 3.0 mCi/mmol, with a radiochemical purity of > 99.5%.

Synthesis and reactions of 3-(N-arylcarbamoyl)-2-methylcinchoninic acid

The Pfitzinger reaction between acetoacetic acid arylamides and the potassium salt of isatinic acid leads in good yield to 3-(N-arylcarbamoyl)-2-methylcinchoninic acids. Refluxing the latter in 2-propanol produced N-substituted imides of 2-methylquinoline-3,4-dicarboxylic acids and, with benzaldehyde in p-xylene in the presence of piperidine, to N-phenylimides of 2-styrylquinoline-3,4-dicarboxylic acids.

Synthesis of [2‐13C]quinoline and [3‐13C]quinoline

Abstract[2‐13C]Quinoline and [3‐13C]quinoline were synthesised by a five‐step process starting from isatin. Acetylation of isatin with acetyl chloride labelled in either the 1‐ or 2‐position, was followed by the pfitzinger reaction to give 2‐hydroxy‐4‐quinoline carboxylic acid labelled in the 2‐or 3‐position. Decarboxylation by pyrolysis was followed by chlorination and reduction to the labelled quinolines. The overall yield was approximately 20%

ChemInform Abstract: A NEW SYNTHESIS OF PYRAZOLO(3,4‐B)QUINOLINE DERIVATIVES

AbstractDie Pyrazolochinolincarbonsäuren (III) und (IV) werden dargestellt.

A New Synthesis of Pyrazolo[3,4-b]quinoline Derivatives

Abstract A new synthesis of pyrazolo[3,4-b]quinoline-4-carboxylic acid derivatives is described. This involves the Pfitzinger reaction of pyrazolone derivatives with isatic acid under controlled conditions. The pyrazoloquinolinecarboxylic acids were converted to their corresponding amides and nitriles, and their absorption and emission characteristics are recorded.

The Pfitzinger reaction with unsymmetrical ketones

The ratios of the products obtained from the Pfitzinger reaction with a series of dialkyl, alkyl arylalkyl, and alkyl aryloxymethylketones have been determined. These results, and the Friedlander reaction on ethyl methyl ketone, show that steric effects have a marked influence on the product ratio from dialkyl ketones, but that with compounds of similar steric requirements in the aromatic series electronic effects are also important. Analysis of the u.v. and n.m.r. spectra of the cinchoninic acids shows that in the 3-unsubstituted compounds the carboxy-group is coplanar with the aromatic rings even when the ring is protonated, but that the carboxy-group of the 3-substituted compounds is very much out of plane except where the substituent is a hydroxy-group. Huckel molecular orbital calculations of π-electron energy and other quantities in the intermediate anions have been carried out.

Some Reactions of 3‐Hydroxy‐6‐Methoxythianaphthene

Abstract3‐Hydroxy‐6‐methoxythianaphthene reacts in its 3‐keto form with various aryl‐, quinolyl‐, and isoquinolyl‐hydrazines to give the corresponding hydrazones, which readily undergo indolisation to the corresponding thianaphthenoindoles. The latter compounds were prepared for testing as potential carcinogens. 3‐Hydroxy‐6‐methoxythianaphthene also condenses in its keto form with isatin, under the conditions of the Pfitzinger reaction.

The Pfitzinger Reaction with Ketones Derived from o-Hydroxydiphenyl

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe Pfitzinger Reaction with Ketones Derived from o-HydroxydiphenylNG. PH. BUU-HOÏ and MICHEL SYCite this: J. Org. Chem. 1956, 21, 1, 136–138Publication Date (Print):January 1, 1956Publication History Published online1 May 2002Published inissue 1 January 1956https://doi.org/10.1021/jo01107a031RIGHTS & PERMISSIONSArticle Views158Altmetric-Citations6LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (349 KB) Get e-Alerts Get e-Alerts

The Utilization of Alkyl 2-Cyclohexylethyl Ketones in the Pfitzinger Reaction1

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe Utilization of Alkyl 2-Cyclohexylethyl Ketones in the Pfitzinger Reaction1Charles G. Skinner and Henry R. HenzeCite this: J. Am. Chem. Soc. 1955, 77, 14, 3810–3813Publication Date (Print):July 1, 1955Publication History Published online1 May 2002Published inissue 1 July 1955https://doi.org/10.1021/ja01619a039RIGHTS & PERMISSIONSArticle Views57Altmetric-Citations6LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (515 KB) Get e-Alerts Get e-Alerts

The Pfitzinger Reaction in the Synthesis of Quinoline Derivatives

The Pfitzinger Reaction in the Synthesis of Quinoline Derivatives

770. The Pfitzinger reaction of p-hydroxypropiophenone and similar phenolic ketones

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58. The chemistry of carcinogenic nitrogen compounds. Part X. The pfitzinger reaction in the synthesis of 1 : 2-benzacridines

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フィツチンガー反應によるイサチンとフェノオキシアセトンの縮合について

Condensation of isatin and phenoxyacetone by the Pfitzinger reaction yields 3-phenoxy-4-quinaldine-carboxylic acid and 2-phenoxymethyl-4-quinoline-carboxylic acid in a 3:1 ratio. It was found that the ether linkage of the phenoxymethyl group in the latter compound is cleaved comparatively easily.

Steric Hindrance in the Pfitzinger Reaction

Steric Hindrance in the Pfitzinger Reaction

Synthesis of 2,3-Disubstituted Cinchoninic Acids from Propoxymethyl Alkyl (or Phenyl) Ketones by Means of the Pfitzinger Reaction1

Synthesis of 2,3-Disubstituted Cinchoninic Acids from Propoxymethyl Alkyl (or Phenyl) Ketones by Means of the Pfitzinger Reaction¹

The Synthesis of Quinolines by the Pfitzinger Reaction

The Synthesis of Quinolines by the Pfitzinger Reaction

Utilization of Alkoxy Ketones in the Synthesis of Quinolines by the Pfitzinger Reaction. II1

Utilization of Alkoxy Ketones in the Synthesis of Quinolines by the Pfitzinger Reaction. II¹