Volume 18, Issue 38
Heterocyclic Compounds
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ChemInform Abstract: A Facile Synthesis of 4-Mercaptoindoles.

M. MATSUMOTO

M. MATSUMOTO

Sagami Chem. Res. Cent., Sagamihara, Kanagawa 229, Japan

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N. WATANABE

N. WATANABE

Sagami Chem. Res. Cent., Sagamihara, Kanagawa 229, Japan

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First published: September 22, 1987

Abstract

The xanthate (III), prepared from the diazonium salt (I), is cleaved by ethylenediamine (IV) to give the mercaptan (Va).

ChemInform Abstract

The xanthate (III), prepared from the diazonium salt (I), is cleaved by ethylenediamine (IV) to give the mercaptan (Va). The corresponding disulfide is obtained from (Va) in the presence of air. Treatment of the xanthate (III) with ethylenediamine (IV) and the halides (VIb) yields the S-substituted 4-mercaptoindoles (Vb). The ester (Vb) (R: -CH2-CO-O-Et) is converted to the pyrrolobenzothiopyran (VIII) which is reduced, forming a cis/trans-mixture of (IX).

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