Synthesis of ethynylindoles

M. S. Shvartsberg, S. F. Vasilevskii, T. A. Prikhod'ko

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

1. Iodine at C-2 and C-3 in the N-methylindole ring are substituted by acetylenic groups under conditions of Pd-Cu catalysis. Condensation of 2-iodo- and 3-iodo-N-methylindole with 2-methyl-3-butyn-2-ol and subsequent cleavage of the indolylacetylenic alcohols yield 2-ethynyl- and 3-ethynyl-N-methylindoles. The condensation of 1-(3′-iodo-1′-methyl-2′-indolyl)-3-methyl-1-butyn-3-ol with 2-methyl-3-butyn-2-ol and subsequent cleavage of the resultant alcohol yield 2,3-diethynyl-N-methylindole. 2. o-Aminophenylacetylenic compounds are cyclized to yield 2-acetylenylindoles. The condensation of o-iodoaniline with 2-methyl-3,5-hexadiyn-2-ol, cyclization of the aminophenyldiacetylene obtained, and alkaline cleavage of the acetylenic alcohol yield 2-ethynylindole.

Original languageEnglish
Pages (from-to)2226-2229
Number of pages4
JournalBulletin of the Academy of Sciences of the USSR Division of Chemical Science
Volume31
Issue number11
DOIs
Publication statusPublished - 1 Nov 1982
Externally publishedYes

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Condensation
Alcohols
Cyclization
Iodine
Catalysis
2-methyl-3-butyn-2-ol
3-butyn-1-ol
3-iodoaniline
acetylenic alcohol

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis of ethynylindoles. / Shvartsberg, M. S.; Vasilevskii, S. F.; Prikhod'ko, T. A.

In: Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, Vol. 31, No. 11, 01.11.1982, p. 2226-2229.

Research output: Contribution to journalArticle

Shvartsberg, M. S. ; Vasilevskii, S. F. ; Prikhod'ko, T. A. / Synthesis of ethynylindoles. In: Bulletin of the Academy of Sciences of the USSR Division of Chemical Science. 1982 ; Vol. 31, No. 11. pp. 2226-2229.
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AB - 1. Iodine at C-2 and C-3 in the N-methylindole ring are substituted by acetylenic groups under conditions of Pd-Cu catalysis. Condensation of 2-iodo- and 3-iodo-N-methylindole with 2-methyl-3-butyn-2-ol and subsequent cleavage of the indolylacetylenic alcohols yield 2-ethynyl- and 3-ethynyl-N-methylindoles. The condensation of 1-(3′-iodo-1′-methyl-2′-indolyl)-3-methyl-1-butyn-3-ol with 2-methyl-3-butyn-2-ol and subsequent cleavage of the resultant alcohol yield 2,3-diethynyl-N-methylindole. 2. o-Aminophenylacetylenic compounds are cyclized to yield 2-acetylenylindoles. The condensation of o-iodoaniline with 2-methyl-3,5-hexadiyn-2-ol, cyclization of the aminophenyldiacetylene obtained, and alkaline cleavage of the acetylenic alcohol yield 2-ethynylindole.

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