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Hypervalent iodine(III)-mediated oxidative acetoxylation of 2-methoxyphenols for regiocontrolled nitrogen benzannulation

Quideau, S, Pouysegu, L, Avellan, AV, Whelligan, DK and Looney, MA (2001) Hypervalent iodine(III)-mediated oxidative acetoxylation of 2-methoxyphenols for regiocontrolled nitrogen benzannulation Tetrahedron Lett, 42 (42). pp. 7393-7396.

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Abstract

Nitrogen-tethered 2-methoxyphenols are conveniently dearomatized into synthetically useful orthoquinol acetates by treatment with phenyliodine(III) diacetate in methylene chloride at low temperature. Subsequent fluoride- or base-induce intramolecular nucleophilic addition reactions furnish indole and quinoline derivatives. The potential of this methodology for the synthesis or a functionalized lycorine-type alkaloid skeleton is introduced here. (C) 2001 Elsevier Science Ltd. All rights reserved.

Item Type: Article
Authors :
NameEmailORCID
Quideau, SUNSPECIFIEDUNSPECIFIED
Pouysegu, LUNSPECIFIEDUNSPECIFIED
Avellan, AVUNSPECIFIEDUNSPECIFIED
Whelligan, DKd.whelligan@surrey.ac.ukUNSPECIFIED
Looney, MAUNSPECIFIEDUNSPECIFIED
Date : 15 October 2001
Uncontrolled Keywords : hypervalent iodine, arene chemistry, oxidative activation, orthoquinol acetate, heterocyclization, IODINE OXIDATION, NUCLEOPHILIC-SUBSTITUTION, TRANSFORMATIONS, ALKALOIDS, REAGENTS, PHENOLS
Depositing User : Symplectic Elements
Date Deposited : 17 May 2017 12:07
Last Modified : 17 May 2017 15:01
URI: http://epubs.surrey.ac.uk/id/eprint/834111

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