Synlett 2006(20): 3439-3442  
DOI: 10.1055/s-2006-956477
LETTER
© Georg Thieme Verlag Stuttgart · New York

Zirconium-Mediated Synthesis of Azepanes and Benzazepanes

Donald P. S. Macfarlanea, David Nortona, Richard J. Whitby*a, David Tupperb
a School of Chemistry, University of Southampton, Southampton, Hants SO17 1BJ, UK
Fax: +44(2380)593781; e-Mail: rjw1@soton.ac.uk;
b Eli Lilly, Erl Wood Manor, Windlesham, Surrey GU20 6PH, UK
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Publikationsverlauf

Received 14 August 2006
Publikationsdatum:
08. Dezember 2006 (online)

Abstract

Intramolecular co-cyclisation of 4- or 5-azanona-1,8-dienes, -enynes and -diynes using zirconocene(1-butene) gives zirconacycles which may be protonated to afford 3,4- or 4,5-disubstituted azepanes or, for the diyne derived systems, reacted with dimethyl acetylenedicarboxylate and CuCl to afford 2- or 3-benz­azepanes.

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Compound 2: 13C NMR (75 MHz, C6D6): δ = 111.0 (CH, 2 × Cp), 56.4 (CH2N), 50.7 (CH2Zr), 48.5 (CH), 47.1 (Me), 40.2 (CH2) ppm.