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Thionation of ω ‐Acylamino Ketones with Lawesson 's Reagent: Convenient Synthesis of 1,3‐Thiazoles and 4 H ‐1,3‐Thiazines
Author(s) -
Nishio Takehiko,
Ori Mayuko
Publication year - 2001
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 - 10.1002/1522-2675(20010815)84:8<2347::aid-hlca2347>3.0.co;2-n
Subject(s) - chemistry , reagent , thiazole , carbon disulfide , disulfide bond , organic chemistry , combinatorial chemistry , medicinal chemistry , biochemistry
The reaction of ω ‐acylamino ketones with Lawesson 's reagent (=2,4‐bis(4‐methoxyphenyl)‐1,3,2,4‐dithiadiphosphetane 2,4‐disulfide; LR ) is described. Treatment of 2‐acylamino ketones 1 ( n =0) with LR gave 1,3‐thiazole derivatives 3 in good yields ( Scheme 1 and Table 1 ). The 4 H ‐1,3‐thiazines 4 were obtained as main products by treatment of 3‐acylamino ketones 2 ( n =1) with an equimolar amount of LR , while mainly the corresponding 3‐(thioacyl)amino ketones 5 were isolated when 0.5 equiv. of LR was used. The 3‐acylamino esters 7 also reacted with LR to give the corresponding 3‐(thioacyl)amino esters 8 ( Scheme 3 and Table 2 ).