Synthesis of 1,2-disubstituted-3-thioindoles by the Madelung reaction

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Abstract

The synthesis of 1,2-disubstituted-3-thioindoles was performed by the Madelung reaction from available starting compounds – benzylsulfides. Under the found conditions [0.2 M benzylsulfide solution in THF, 2 eq LDA], 1,2-disubstituted-3-thioindoles with electron-donor and electron-acceptor substituents at the 5 and 6 positions, as well as with aromatic and aliphatic substituents at the sulfur were obtained. The products were obtained in high yields (from 62 to 93%).

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About the authors

G. K. Sterligov

Topchiev Institiute of Petrochemical Synthesis, Russian Academy of Sciences

Email: aasachenko@ips.ac.ru
ORCID iD: 0000-0002-0922-1964
Russian Federation, Leninskii prosp., 29, Moscow, 119991

M. A. Rasskazova

Topchiev Institiute of Petrochemical Synthesis, Russian Academy of Sciences

Email: aasachenko@ips.ac.ru
ORCID iD: 0000-0002-6637-6866
Russian Federation, Leninskii prosp., 29, Moscow, 119991

M. A. Topchiy

Topchiev Institiute of Petrochemical Synthesis, Russian Academy of Sciences

Email: aasachenko@ips.ac.ru
ORCID iD: 0000-0002-6604-7034
Russian Federation, Leninskii prosp., 29, Moscow, 119991

A. F. Asachenko

Topchiev Institiute of Petrochemical Synthesis, Russian Academy of Sciences

Author for correspondence.
Email: aasachenko@ips.ac.ru
ORCID iD: 0000-0001-8638-9261
Russian Federation, Leninskii prosp., 29, Moscow, 119991

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2. Scheme 1. Examples of biologically active 1,2-disubstituted-3-thioindoles

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3. Scheme 2. Synthesis of 1,2-diphenyl-3-thioindoles 2a–2i via the Madelung reaction

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4. Figure

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