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Chemistry of the phenoxathiins and isosterically related heterocycles. 25. Synthesis of 1,6-diazathianthrene from 3-mercaptopyridin-2(1H)-thione via a novel dehydrothiolation reaction in the presence of triethylamine. [Novel Heterocyclic systems. 13]

Puig-torres, Salvador, Womack, Charles H., Martin, Gary E. and Smith, Keith 1982. Chemistry of the phenoxathiins and isosterically related heterocycles. 25. Synthesis of 1,6-diazathianthrene from 3-mercaptopyridin-2(1H)-thione via a novel dehydrothiolation reaction in the presence of triethylamine. [Novel Heterocyclic systems. 13]. Journal of Heterocyclic chemistry 19 (6) , pp. 1561-1563. 10.1002/jhet.5570190665

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Abstract

The generation of the dianion of 3-mercaptopyridin-2(1H)-thione with triethylamine in N,N-dimethylform-amide followed by reaction in the presence of 2-chloronitrobenzene fails to give 1-azathianthrene which is formed in good yield when sodium hydride was employed as the base. The principle product isolated from the reaction was instead 1,6-diazathianthrene. Mechanistic considerations are discussed.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Additional Information: For the previous paper in this series, see: “Chemistry of the Phenoxathiins and Isosterically Related Heterocycles. XXIV. Synthesis and Characterization by 13C-NMR Spectroscopy of Isomeric Benzoxathiinopyridazinones: 1-oxo-1,2-dihydro-2,3-diazaphenoxathiin and 4-oxo-3,4 3,4-dihydro-2,3-diazaphenoxathiin. The First Observation of a Smiles Rearrangement involving Divalent Sulfur during the Synthesis of an Azaphenoxathiin”, C. H. Womack, L. M. Martin, G. E. Martin and K. Smith, J. Heterocyclic Chem., 19, 1447 (1982). The present work also represents Part 13 in the series Novel Heterocyclic systems.
Publisher: Wiley
ISSN: 0022-152x
Last Modified: 04 Jun 2017 02:57
URI: http://orca.cf.ac.uk/id/eprint/14523

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