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

✍ Scribed by Elwira Chrobak; Andrzej Maślankiewicz

Book ID: 102892973
Publisher: Journal of Heterocyclic Chemistry
Year: 2008
Tongue: English
Weight: 501 KB
Volume: 45
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570450436

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✦ Synopsis

Abstract

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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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