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Zirconium-mediated synthesis of azepanes and benzazepanes

Zirconium-mediated synthesis of azepanes and benzazepanes
Zirconium-mediated synthesis of azepanes and benzazepanes
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.
zirconacyclopentadienes, benzazepanes, receptor, analogs, azepanes, alkynes, promoted, cyclization, carbonylation, 4-disubstituted piperidines, metallacycles, heterocycles, 3, reduced isoquinolines, benzene-derivatives, zirconium
0936-5214
3439-3442
Macfarlane, Donald P.S.
321775c5-d95d-4831-b5d9-534463c45185
Norton, David
4c63fcf9-0fc8-4623-b414-443d4658bbed
Whitby, Richard J.
45632236-ab00-4ad0-a02d-6209043e818b
Tupper, David
e5c65499-83aa-44c3-bda9-1d49d6ef7525
Macfarlane, Donald P.S.
321775c5-d95d-4831-b5d9-534463c45185
Norton, David
4c63fcf9-0fc8-4623-b414-443d4658bbed
Whitby, Richard J.
45632236-ab00-4ad0-a02d-6209043e818b
Tupper, David
e5c65499-83aa-44c3-bda9-1d49d6ef7525

Macfarlane, Donald P.S., Norton, David, Whitby, Richard J. and Tupper, David (2006) Zirconium-mediated synthesis of azepanes and benzazepanes. Synlett, (20), 3439-3442. (doi:10.1055/s-2006-956477).

Record type: Article

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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More information

Published date: December 2006
Keywords: zirconacyclopentadienes, benzazepanes, receptor, analogs, azepanes, alkynes, promoted, cyclization, carbonylation, 4-disubstituted piperidines, metallacycles, heterocycles, 3, reduced isoquinolines, benzene-derivatives, zirconium

Identifiers

Local EPrints ID: 54218
URI: http://eprints.soton.ac.uk/id/eprint/54218
ISSN: 0936-5214
PURE UUID: 7c24e14c-afa2-4099-9c7c-5db29e1863a5
ORCID for Richard J. Whitby: ORCID iD orcid.org/0000-0002-9891-5502

Catalogue record

Date deposited: 29 Jul 2008
Last modified: 19 Nov 2019 02:04

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