Two-Step Route to Diverse N-Functionalized Peptidomimetic-like Isatins through an Oxidation/Intramolecular Oxidative-Amidation Cascade of Ugi Azide and Ugi Three-Component Reaction Products

Christopher Foley; Arthur Shaw; Christopher Hulme

doi:10.1021/acs.orglett.6b02383

Two-Step Route to Diverse N-Functionalized Peptidomimetic-like Isatins through an Oxidation/Intramolecular Oxidative-Amidation Cascade of Ugi Azide and Ugi Three-Component Reaction Products

Christopher Foley, Arthur Shaw, Christopher Hulme

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

25 Scopus citations

Abstract

Two-step methodology described herein showcases the first example of an oxidation/oxidative amidation cyclization cascade of MCR products toward diverse N-functionalized isatins. Products of both the Ugi 3CR and the Ugi azide reactions are oxidatively cyclized through a postcondensation process utilizing selenium dioxide. This methodology was found to be applicable for the generation of bis-peptidomimetic-like isatins containing multiple points of diversification.

Original language	English (US)
Pages (from-to)	4904-4907
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.6b02383
State	Published - Oct 7 2016

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Two-Step Route to Diverse N-Functionalized Peptidomimetic-like Isatins through an Oxidation/Intramolecular Oxidative-Amidation Cascade of Ugi Azide and Ugi Three-Component Reaction Products. / Foley, Christopher; Shaw, Arthur; Hulme, Christopher.

In: Organic Letters, Vol. 18, No. 19, 07.10.2016, p. 4904-4907.

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

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AB - Two-step methodology described herein showcases the first example of an oxidation/oxidative amidation cyclization cascade of MCR products toward diverse N-functionalized isatins. Products of both the Ugi 3CR and the Ugi azide reactions are oxidatively cyclized through a postcondensation process utilizing selenium dioxide. This methodology was found to be applicable for the generation of bis-peptidomimetic-like isatins containing multiple points of diversification.

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Two-Step Route to Diverse N-Functionalized Peptidomimetic-like Isatins through an Oxidation/Intramolecular Oxidative-Amidation Cascade of Ugi Azide and Ugi Three-Component Reaction Products

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