Reactions of 4-dimethylamino-3-quinolinyl sulfides with nitrating mixture and transamination of 4-dimethylamino-3-methylsulfinyl-6-nitroquinoline

Elwira Chrobak,

Elwira Chrobak

Department of Organic Chemistry, The Medical University of Silesia, 4 Jagiellońska, 41-200 Sosnowiec, Poland

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Andrzej Maślankiewicz,

Andrzej Maślankiewicz

[email protected]

Department of Organic Chemistry, The Medical University of Silesia, 4 Jagiellońska, 41-200 Sosnowiec, Poland

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Elwira Chrobak,

Elwira Chrobak

Department of Organic Chemistry, The Medical University of Silesia, 4 Jagiellońska, 41-200 Sosnowiec, Poland

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Andrzej Maślankiewicz,

Andrzej Maślankiewicz

[email protected]

Department of Organic Chemistry, The Medical University of Silesia, 4 Jagiellońska, 41-200 Sosnowiec, Poland

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First published: 13 March 2009

https://doi.org/10.1002/jhet.5570450436

Citations: 3

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Abstract

4-Amino-3-quinolinyl sulfides 4d-e and 7a-c were prepared by amination of 4-chloro-3-quinolinyl sulfides 4c or 1c, respectively, in methanol (140-160 °C) or in boiling phenol with yields up to 95 %. Reaction of 4-dimethylamino-3-quinolinyl sulfides 7c and 4e with nitrating mixture proceeded simultanously as oxidation of the methylthio group to the methylsulfinyl one and as C6-nitration to form 6-nitro-β-quinolinyl sulfoxides 9c or 10b, respectively. 4-Dimethylamino-3-methylsulfinyl-6-nitroquinoline 9c underwent acid catalysed transamination when reacting with primary aliphatic amines and ammonia.

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Volume45, Issue4

July/August 2008

Pages 1171-1177

Reactions of 4-dimethylamino-3-quinolinyl sulfides with nitrating mixture and transamination of 4-dimethylamino-3-methylsulfinyl-6-nitroquinoline

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Reactions of 4-dimethylamino-3-quinolinyl sulfides with nitrating mixture and transamination of 4-dimethylamino-3-methylsulfinyl-6-nitroquinoline

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