Zirconium-Mediated Synthesis of Azepanes and Benzazepanes

Donald P. S. Macfarlane; David Norton; Richard J. Whitby; David Tupper

doi:10.1055/s-2006-956477

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2006(20): 3439-3442
DOI: 10.1055/s-2006-956477

LETTER

Zirconium-Mediated Synthesis of Azepanes and Benzazepanes

Donald P. S. Macfarlane^a, David Norton^a, Richard J. Whitby*^a, David Tupper^b
^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

Further Information

Publication History

Received 14 August 2006
Publication Date:
08 December 2006 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

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.

Key words

zirconium - azepanes - benzazepanes - heterocycles - metallacycles

References

1 Neumeyer JL. Kula NS. Baldessarini RJ. Baindur N. J. Med. Chem. 1992, 35: 1466

Crossref Google Scholar
2 Neumeyer JL. Kula NS. Bergman J. Baldessarini RJ. Eur. J. Pharmacol. 2003, 474: 137

Crossref Google Scholar
3 Neumeyer JL. Baldessarini RJ. In Therapeutic and Diagnostic Agents for Parkinson’s Disease Abraham DJ. Wiley; New York: 2003. p.711

Google Scholar
4 Karlsson P. Smith L. Farde L. Harnryd C. Sedvall G. Wiesel FA. Psychopharmacology 1995, 121: 309

Google Scholar
5 Kawase M. Saito S. Motohashi N. Int. J. Antimicrob. Agents 2000, 14: 193

Google Scholar
6 Clark MT. Chang J. Navran SS. Akbar H. Mukhopadhyay A. Amin H. Feller DR. Miller DD. J. Med. Chem. 1986, 29: 181

Crossref Google Scholar
7a Mori M. Imai AE. Uesaka N. Heterocycles 1995, 40: 551

Crossref Google Scholar
7b Bird AJ. Taylor RJK. Wei X. Synlett 1995, 1237

Crossref Google Scholar
For coupling of N,N-diallylamines:
7c Uesaka N. Mori M. Okamura K. Date T. J. Org. Chem. 1994, 59: 4542

Crossref Google Scholar
7d Rousset CJ. Swanson DR. Lamaty F. Negishi E. Tetrahedron Lett. 1989, 30: 5105

Crossref Google Scholar
7e For coupling of N-allyl-N-propargylamines: Mori M. Uesaka N. Saitoh F. Shibasaki M. J. Org. Chem. 1994, 59: 5643

Crossref Google Scholar
8a Kemp MI. Whitby RJ. Coote SJ. Synthesis 1998, 557

Article in Thieme Connect Google Scholar
8b Kemp MI. Whitby RJ. Coote SJ. Synthesis 1998, 552

Article in Thieme Connect Google Scholar
9 Barluenga J. Sanz R. Fananás F. Chem. Eur. J. 1997, 3: 1324

Crossref Google Scholar
10a Negishi E. Holmes SJ. Tour JM. Miller JA. Cederbaum FE. Swanson DR. Takahashi T. J. Am. Chem. Soc. 1989, 111: 3336

Google Scholar
10b Negishi E. Cederbaum FE. Takahashi T. Tetrahedron Lett. 1986, 27: 2929

Google Scholar
12a Harvey AL. Pharmacol. Ther. 1995, 68: 113

Google Scholar
12b Bores GM. Kosley RW. Drugs Future 1996, 21: 621

Google Scholar
13 Nugent WA. Calabrese JC. J. Am. Chem. Soc. 1984, 106: 6422

Crossref Google Scholar
14 Kemp MI. Whitby RJ. Coote SJ. Synlett 1994, 451

Article in Thieme Connect Google Scholar
15 Takahashi T. Kotora M. Xi ZF. J. Chem. Soc., Chem. Commun. 1995, 361

Crossref Google Scholar
16 Takahashi T. Xi ZF. Yamazaki A. Liu YH. Nakajima K. Kotora M. J. Am. Chem. Soc. 1998, 120: 1672

Crossref Google Scholar
17 Datta A. Ila H. Junjappa H. J. Org. Chem. 1990, 55: 5589

Crossref Google Scholar
18 Wu WL. Burnett DA. Spring R. Greenlee WJ. Smith M. Favreau L. Fawzi A. Zhang HT. Lachowicz JE. J. Med. Chem. 2005, 48: 680

Crossref Google Scholar

11

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.