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Sonogashira/N-acyliminium ion aromatic π-cyclisation processes: access to tetra- and pentacyclic lactams

Grigg, R., Sridharan, V. and Sykes, D.A. (2008) Sonogashira/N-acyliminium ion aromatic π-cyclisation processes: access to tetra- and pentacyclic lactams. Tetrahedron, 64 (37). pp. 8952-8962. ISSN 0040-4020

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Abstract

Application of the Sonogashira reaction of N-alkynylimides with 2-iodophenol or 2-iodo-N-tosylaniline affords 2-(N-alkylimino)-benzofurans and indoles in good yield. Selective partial reduction of the latter followed by treatment with TsOH generates N-acyliminium ions, which cyclise to afford tetra- and pentacyclic lactams in good yield. The latter are reduced to the analogous cyclic amines by BH3.

Item Type: Article
Copyright, Publisher and Additional Information: © 2008 Elsevier B.V. This is an author produced version of a paper published in Tetrahedron. Uploaded in accordance with the publisher's self archiving policy.
Academic Units: The University of Leeds > Faculty of Maths and Physical Sciences (Leeds) > School of Chemistry (Leeds)
Depositing User: Sherpa Assistant
Date Deposited: 16 Oct 2008 10:31
Last Modified: 08 Feb 2013 17:05
Published Version: http://dx.doi.org/10.1016/j.tet.2008.06.044
Status: Published
Publisher: Elsevier B.V.
Refereed: Yes
Identification Number: 10.1016/j.tet.2008.06.044
URI: http://eprints.whiterose.ac.uk/id/eprint/4752

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