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Sulfur‐Containing Heterocycles Derived by Reaction of ω‐Keto Amides with Lawesson 's Reagent
Author(s) -
Nishio Takehiko
Publication year - 1998
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19980810531
Subject(s) - chemistry , reagent , yield (engineering) , sulfur , medicinal chemistry , disulfide bond , organic chemistry , biochemistry , materials science , metallurgy
The reaction of ω‐keto amides with Lawesson 's reagent ( LR : 2,4‐bis(4‐methoxyphenyl)‐1,3,2,4‐dithiadiphosphetane 2,4‐disulfide) is described. Treatment of 3‐keto amides (2‐acylacetamides) 1 with LR gave the corresponding 3‐keto thioamides 2 , along with 1,2‐dithiole‐3‐thiones 3 . Treatment of 4‐keto amides, 3‐acyl propionamides 5 , with LR yielded five‐membered heterocycles, pyrroles 6 and/or 2‐aminothiophenes 7 . 5‐Keto amides, 3‐benzoyl butyramides 8 , reacted with LR to give dihydrothiopyran‐2‐thione 9 as the sole product, but in low yield. 2‐Acylbenzamides 10 also reacted with LR to afford 3‐mercaptoisoindolin‐2‐ones 11 or dihydroisobenzothiophene‐1‐thiones 12 .
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