Tetrahedron

Iodine-induced iminothiolactonization of γ, δ-unsaturated secondary thio-amides. new entry to 2-acetoamidothiophenes

H Takahata, T Suzuki, M Maruyama, K Moriyama…

Index: Takahata, Hiroki; Suzuki, Toshiaki; Maruyama, Mihoko; Moriyama, Keiko; Mozumi, Mayumi; et.al. Tetrahedron, 1988 ,  vol. 44,  # 15  p. 4777 - 4786

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Citation Number: 14

Abstract

Iodine-induced cyclization of γ, δ-unsaturated secondary thioamides 1 proceeded regio-(5- exo-trigonal) and chemo-(sulfur-carbon bond formation) selectively, providing iminothiolactones 2, which were converted in two-step sequences (dehydroiodination and N- acetylation) into 2-acetoamidothiophenes 4. This procedure was performed in one flask to afford polysubstituted 2-aminothiophenes.