Issue 2, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis of 6-alkyl analogues of the 1-azabicyclo[4.3.0]nonan-2-one system by a strategy of geminal acylation and Beckmann rearrangement

Christine E. Elliott,a   David O. Millera  and  D. Jean Burnell*a  

* Corresponding authors

a Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland, A1B 3X7, Canada
E-mail: jburnell@mun.ca
Fax: 709-737-3702
Tel: 709-737-8535

Abstract

Compounds with the 1-azabicyclo[4.3.0]nonan-2-one nucleus have been prepared with methyl and isobutyl groups at C-6. The synthetic sequence was: geminal acylation to produce a but-2-enylcyclopentane-1,3-dione derivative, treatment with O-mesitylenesulfonylhydroxylamine and then Beckmann rearrangement with BF3·Et2O and cyclization of the amidic nitrogen onto the terminal double bond. In addition, the results of exploratory reactions are presented.

Graphical abstract: Synthesis of 6-alkyl analogues of the 1-azabicyclo[4.3.0]nonan-2-one system by a strategy of geminal acylation and Beckmann rearrangement

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Article information

DOI
https://doi.org/10.1039/B108164K
Article type
Paper
Submitted
10 Sep 2001
Accepted
13 Nov 2001
First published
18 Dec 2001

J. Chem. Soc., Perkin Trans. 1, 2002, 217-226

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Synthesis of 6-alkyl analogues of the 1-azabicyclo[4.3.0]nonan-2-one system by a strategy of geminal acylation and Beckmann rearrangement

C. E. Elliott, D. O. Miller and D. J. Burnell, J. Chem. Soc., Perkin Trans. 1, 2002, 217 DOI: 10.1039/B108164K

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