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Thionation of N-(ω-Halogenoalkyl)-Substituted Amides with Lawesson's Reagent: Facile Synthesis of 4,5-Dihydro-1,3-thiazoles and 5,6-Dihydro-4H-1,3-thiazines

✍ Scribed by Yasuhiro Kodama; Mayuko Ori; Takehiko Nishio

Publisher: John Wiley and Sons
Year: 2005
Tongue: German
Weight: 88 KB
Volume: 88
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200590000

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✦ Synopsis

The thionation and cyclization of N-(w-halogenoalkyl)-substituted amides (and related compounds) with Lawessons reagent (LR 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide) has been investigated. Treatment of the amides 1 with LR gave the corresponding thioamides 2 in moderate to good yields (Table ). The latter, upon treatment with base, afforded, either in a separate step or in a one-pot procedure, the cyclized title compounds, i.e., the 4,5-dihydro-1,3-thiazoles 3 or the corresponding 5-6-dihydro-4H-thiazines 4 via dehydrohalogenation.

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