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
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.
|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.|
|Institution:||The University of Leeds|
|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:||16 Sep 2016 13:37|