General and facile synthesis of indoles with oxygen-bearing substituents at the benzene moiety

Yoshinori Kondo; Satoshi Kojima; Takao Sakamoto

doi:10.1021/jo970377w

General and facile synthesis of indoles with oxygen-bearing substituents at the benzene moiety

Yoshinori Kondo, Satoshi Kojima, Takao Sakamoto

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

123 Citations (Scopus)

Abstract

Indoles with oxygen-bearing substituents such as a methoxy or (triisopropylsilyl)oxy group at all of the positions of the benzene moiety were synthesized by cyclization of tert-butyl methoxy(or (triisopropylsilyl)oxy)-2-((trimethylsilyl)ethynyl)phenyl)carbamates with potassium tert-butoxide in tert-butyl alcohol. The (ethynylphenyl)carbamates were synthesized by the palladium-catalyzed reaction of (trimethylsilyl)acetylene and the corresponding (iodophenyl)carbamates, which were selectively synthesized by directed lithiation of the phenylcarbamates and subsequent iodination.

Original language	English
Pages (from-to)	6507-6511
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	62
Issue number	19
DOIs	https://doi.org/10.1021/jo970377w
Publication status	Published - 1997 Jan 1

ASJC Scopus subject areas

Organic Chemistry

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abstract = "Indoles with oxygen-bearing substituents such as a methoxy or (triisopropylsilyl)oxy group at all of the positions of the benzene moiety were synthesized by cyclization of tert-butyl methoxy(or (triisopropylsilyl)oxy)-2-((trimethylsilyl)ethynyl)phenyl)carbamates with potassium tert-butoxide in tert-butyl alcohol. The (ethynylphenyl)carbamates were synthesized by the palladium-catalyzed reaction of (trimethylsilyl)acetylene and the corresponding (iodophenyl)carbamates, which were selectively synthesized by directed lithiation of the phenylcarbamates and subsequent iodination.",

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AU - Kondo, Yoshinori

AU - Kojima, Satoshi

AU - Sakamoto, Takao

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AB - Indoles with oxygen-bearing substituents such as a methoxy or (triisopropylsilyl)oxy group at all of the positions of the benzene moiety were synthesized by cyclization of tert-butyl methoxy(or (triisopropylsilyl)oxy)-2-((trimethylsilyl)ethynyl)phenyl)carbamates with potassium tert-butoxide in tert-butyl alcohol. The (ethynylphenyl)carbamates were synthesized by the palladium-catalyzed reaction of (trimethylsilyl)acetylene and the corresponding (iodophenyl)carbamates, which were selectively synthesized by directed lithiation of the phenylcarbamates and subsequent iodination.

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