Reactions of some N-(2,5-dimethoxyaryl)thiobenzamides: en route to an analogue of kuanoniamine A

Jackson, Yvette A.; Lyon, Michael A.; Townsend, Norman; Bellabe, Kettyna; Soltanik, Fernando

doi:10.1039/a907633f

Cited by 22 publications

(14 citation statements)

References 12 publications

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“…The N-arylthiobenzamides were prepared from the corresponding anilines by benzoylation and subsequent sulfurization. [3][4][5][6][7] Scheme 2 N-Arylthiobenzamides 1e (Scheme 3) was prepared from 2,4-dimethoxyaniline (5) (Scheme 3). N-Arylthiobenzamide 1l was obtained by sulfurization of N-arylthiobenzamide 7 in 97% yield.…”

Section: Methodsmentioning

confidence: 99%

Thermally Induced Cyclization of Electron-Rich N-Arylthiobenzamides to Benzothiazoles

2012

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Section: Methodsmentioning

confidence: 99%

Thermally Induced Cyclization of Electron-Rich N-Arylthiobenzamides to Benzothiazoles

2012

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“…The regioselective synthesis of substituted 2-arylbenzothiazoles under Jacobsen conditions (or using azobisisobutyronitrile (AIBN)) has also been reported via an unusual ipso substitution of orthomethoxythiobenzamides [86,87], and via intramolecular displacement of fluoride [88,89] or chloride/iodide under photochemical conditions [90,91].…”

Section: Via Thioamide Cyclisationmentioning

confidence: 99%

2-Arylbenzothiazole as a Privileged Scaffold in Drug Discovery

Weekes

Westwell²

2009

CMC

143

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Substituted 2-arylbenzothiazoles have emerged in recent years as an important pharmacophore in a number of diagnostic and therapeutic settings. Attractive features of drug candidates based on this benzothiazole scaffold include their synthetic accessibility, and synthetic approaches to 2-arylbenzothiazole-based compounds will be reviewed here. Examples of 2-arylbenzothiazoles endowed with diagnostic/therapeutic activity include the 2-(4-aminophenyl)benzothiazole series, which has a remarkable activity profile in both the potential non-invasive diagnosis of Alzheimer's disease and as antitumour agents.

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“…The pyridine ring in the precursor 48 of an analog of Kuanoniamide A is formed with the use of methyl vinyl ketone [77,78] In the examples presented above the preferential formation of tricyclic systems with angular fusion of the rings is observed in both the Skraup and the Doebner-Miller reactions even if there is an alternative cyclization path. However, the formation of compound 48 with linear structure is possible if there is one substituted ortho position in relation to the amino group (e.g., with the presence of a methoxy group).…”

Section: Synthesis Of Polycyclic Derivatives Of Quinoline Using the Smentioning

confidence: 99%

Traditional and modern approaches to the synthesis of quinoline systems by the Skraup and Doebner-Miller methods. (Review)

Yamashkin

Oreshkina

2006

Chem Heterocycl Compd

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Recent data on classical and modified methods for the synthesis of quinoline systems by the Skraup andDoebner-Miller reactions, not included in reviews on heterocycles, are discussed.The need for compounds containing a quinoline fragment in various regions of human activity has increased in recent times. The great attention paid by researchers to the study of quinoline derivatives is explained by the fact that these compounds exhibit a broad range of antimicrobial activity [1-4] and, particularly, antitubercular activity [5] and antimalarial activity [6,7] and are also present in antiallergic and antiasthmatic agents [8]. Classical methods are widely used for their synthesis, and two of these are discussed in the present review.The most important way of constructing the quinoline system involves the cyclization of a substituent in the side chain of a benzene ring. This applies to the synthesis of quinolines by the Skraup and Doebner-Miller reactions. In the classical form, however, these syntheses take place under fairly harsh conditions, and this reduces their preparative value. In recent years, however, the efforts of synthetic chemists have been directed toward modification of these methods. Both traditional and modified approaches to the synthesis are discussed in this review.The first report on the synthesis of quinoline, realized by passing the vapor of ethylaniline and other alkylanilines over heated lead oxide, was published by Koenigs in 1879; in another method (1880) quinoline was obtained by heating the product from the addition of acrolein to aniline. Soon after this Skraup (1880) [9] and Doebner and Miller (1881) put forward their methods [10]; both these syntheses are close to Koenigs' acrolein method and have found widespread application. THE SKRAUP AND DOEBNER-MILLER REACTIONS (THE TRADITIONAL APPROACH)The construction of the quinoline system by the Skraup and Doebner-Miller methods is based on the reaction of an aromatic amine containing at least one free ortho position with a reagent providing a source of the three-carbon fragment.In the classical Skraup method the aromatic amine is heated with glycerol (1), sulfuric acid (which catalyzes the dehydration of glycerol to acrolein (2)), and an oxidizing agent 7, transforming the initially formed 1,2-dihydroquinoline (6) into the fully aromatized heterocycle 8. In the simplest case, with aniline (3) as amine and nitrobenzene (7) as oxidizing agent, the reaction is represented by the following scheme [11]. __________________________________________________________________________________________

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Reactions of some N-(2,5-dimethoxyaryl)thiobenzamides: en route to an analogue of kuanoniamine A

Cited by 22 publications

References 12 publications

Thermally Induced Cyclization of Electron-Rich N-Arylthiobenzamides to Benzothiazoles

Thermally Induced Cyclization of Electron-Rich N-Arylthiobenzamides to Benzothiazoles

2-Arylbenzothiazole as a Privileged Scaffold in Drug Discovery

Traditional and modern approaches to the synthesis of quinoline systems by the Skraup and Doebner-Miller methods. (Review)

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