A New Indole Synthesis Promoted by Metal Triflates

Alan P. Kozikowski, Xue‐Min ‐M Cheng, Chun‐Sing ‐S Li, James G. Scripko

Research output: Contribution to journalArticle

Abstract

A new synthesis of 4‐ and 7‐carbon‐substituted indoles is described. The overall sequence involves the addition of a nitrile oxide to 1 carboethoxy‐2‐(or 3‐) allylpyrrole, hydrogenation of the intermediate isoxazoline to β‐hydroxy ketone and cyclization of the ketol using magnesium or zinc triflate to the substituted indole. This new indole‐forming strategy can also accommodate the introduction of oxygen functionality into the indole 6‐position. Possible mechanistic aspects of the reaction are detailed.

Original languageEnglish (US)
Pages (from-to)61-65
Number of pages5
JournalIsrael Journal of Chemistry
Volume27
Issue number1
DOIs
StatePublished - 1986
Externally publishedYes

Fingerprint

Metals
Indoles
Nitriles
Cyclization
Ketones
Oxides
Magnesium
Hydrogenation
Oxygen
indole
trifluoromethanesulfonic acid

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Kozikowski, A. P., Cheng, XM. M., Li, CS. S., & Scripko, J. G. (1986). A New Indole Synthesis Promoted by Metal Triflates. Israel Journal of Chemistry, 27(1), 61-65. https://doi.org/10.1002/ijch.198600011

A New Indole Synthesis Promoted by Metal Triflates. / Kozikowski, Alan P.; Cheng, Xue‐Min ‐M; Li, Chun‐Sing ‐S; Scripko, James G.

In: Israel Journal of Chemistry, Vol. 27, No. 1, 1986, p. 61-65.

Research output: Contribution to journalArticle

Kozikowski, AP, Cheng, XMM, Li, CSS & Scripko, JG 1986, 'A New Indole Synthesis Promoted by Metal Triflates', Israel Journal of Chemistry, vol. 27, no. 1, pp. 61-65. https://doi.org/10.1002/ijch.198600011
Kozikowski, Alan P. ; Cheng, Xue‐Min ‐M ; Li, Chun‐Sing ‐S ; Scripko, James G. / A New Indole Synthesis Promoted by Metal Triflates. In: Israel Journal of Chemistry. 1986 ; Vol. 27, No. 1. pp. 61-65.
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