Synthesis of Benzothiazoles via ipso Substitution of ortho‐Methoxythiobenzamides.

Downer, Nadale K.; Jackson, Yvette A.

doi:10.1002/chin.200510132

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Via Thioamide Cyclisation1

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2009

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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

144

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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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