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First synthesis of 3-mercapto-2(1H)-pyridinone, a simple disubstituted pyridine useful for synthesis of the 4-azaphenoxathiine ring system and its novel diazaphenoxathiine analogs: 1,6-Diazaphenoxathiine and 2,6-diazaphenoxathiine

Smith, Keith, Anderson, Dorian and Matthews, Ian 1996. First synthesis of 3-mercapto-2(1H)-pyridinone, a simple disubstituted pyridine useful for synthesis of the 4-azaphenoxathiine ring system and its novel diazaphenoxathiine analogs: 1,6-Diazaphenoxathiine and 2,6-diazaphenoxathiine. Journal of organic chemistry 61 (2) , pp. 662-665. 10.1021/jo951254j

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Abstract

3-Mercapto-2(1H)-pyridinone (1) can be synthesized in three simple high-yielding steps from readily available 2-tert-butylthiazolo[4,5-b]pyridine (2). Its disodium salt condenses with o-chloronitrobenzene, 2-chloro-3-nitropyridine, and 3-chloro-4-nitropyridine 1-oxide to give respectively 4-azaphenoxathiine (10), 1,6-diazaphenoxathiine (12), and 2,6-diazaphenoxathiine 2-oxide (14) which reduces to 2,6-diazaphenoxathiine (15). The structures of these previously unreported azaphenoxathiine systems were confirmed by assignment of their respective 13C NMR spectra.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: American Chemical Society
ISSN: 0022-3263
Last Modified: 04 Jun 2017 02:51
URI: http://orca.cf.ac.uk/id/eprint/12730

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