Tetrahedron p. 5017 - 5026 (1999)
Update date:2022-09-26
Topics:
Nishio, Takehiko
Sekiguchi, Hiroshi
The thionation of ω-hydroxy amides with Lawesson's reagent [LR: 2,4- bis(p-methoxyphenyl)-1,3,2,4-dithiaphosphetane-2,4-disulfide] is described. The treatment of 3-hydroxy amides 1 with LR exclusively gave thioenamides 2 in fair yields. The treatment of 4-hydroxy amides 5 with LR yielded sulfur- containing heterocycles such as tetrahydrothiophene-2-imines 6 and tetrahydrothiophene-2-thione 7a through cyclization of intermediates, 4- mercapto amides 8. The 5-hydroxy amides 13 also reacted with LR to afford tetrahydrothiopyrane-2-thione 14 as the the sole product.
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