A New Indole Synthesis Promoted by Metal Triflates

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

doi:10.1002/ijch.198600011

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 journal › Article › peer-review

4 Scopus citations

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 language	English (US)
Pages (from-to)	61-65
Number of pages	5
Journal	Israel Journal of Chemistry
Volume	27
Issue number	1
DOIs	https://doi.org/10.1002/ijch.198600011
State	Published - 1986
Externally published	Yes

ASJC Scopus subject areas

General Chemistry

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10.1002/ijch.198600011

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title = "A New Indole Synthesis Promoted by Metal Triflates",

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.",

author = "Kozikowski, {Alan P.} and Cheng, {Xue‐Min ‐M} and Li, {Chun‐Sing ‐S} and Scripko, {James G.}",

year = "1986",

doi = "10.1002/ijch.198600011",

language = "English (US)",

volume = "27",

pages = "61--65",

journal = "Israel Journal of Chemistry",

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publisher = "Wiley-VCH Verlag",

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T1 - A New Indole Synthesis Promoted by Metal Triflates

AU - Kozikowski, Alan P.

AU - Cheng, Xue‐Min ‐M

AU - Li, Chun‐Sing ‐S

AU - Scripko, James G.

PY - 1986

Y1 - 1986

N2 - 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.

AB - 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.

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U2 - 10.1002/ijch.198600011

DO - 10.1002/ijch.198600011

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SP - 61

EP - 65

JO - Israel Journal of Chemistry

JF - Israel Journal of Chemistry

IS - 1

ER -

A New Indole Synthesis Promoted by Metal Triflates

Abstract

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