IODINE-INDUCED IMINOTHIOLACTONIZATION OF γ,δ-UNSATURATED SECONDARY THIOAMIDES, NEW ENTRY TO 2-ACETOAMIDOTHIOPHENES

DOI: 10.1016/S0040-4020(01)86180-9

Source and publish data:

Tetrahedron p. 4777 - 4786 (1988)

Update date:2022-08-04

Topics:

Authors:

Takahata, Hiroki

Suzuki, Toshiaki

Maruyama, Mihoko

Moriyama, Keiko

Mozumi, Mayumi

et.al. et.al.

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Article abstract of DOI:10.1016/S0040-4020(01)86180-9

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.

Full text of DOI:10.1016/S0040-4020(01)86180-9

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