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- Title
Synthesis of 3-Aminotropones from N-Boc-Protected Furan-2-amine (=tert-Butyl Furan-2-ylcarbamate; Boc=(tert-Butoxy)carbonyl) by Cycloaddition Reactions and Subsequent Rearrangement.
- Authors
Ángel 4;M. Montaña; Juan 4;A. Barcia; Gabriele Kociok-Köhn; Mercè Font-Bardia; Xavier Solans
- Abstract
The 3-aminotropones (=3-aminocyclohepta-2,4,6-trien-1-ones) 4 were prepared in two steps by i) a [4+3] cycloaddition reaction between a conveniently substituted α,α′-dihalo ketone 1 and a furan-2-amine derivative 2 functionalized at C(2) by a protected amino group (→3), and ii) a base-induced molecular rearrangement of the cycloadduct 3via cleavage of the O-bridge. A mechanism for the formation of 3-aminotropones is proposed on the basis of the initial deprotonation of the [(tert-butoxy)carbonyl]amino (BocNH) group of 3, followed by O-bridge opening, an acid–base equilibrium, and finally an alkoxyaluminate elimination to afford the conjugated stable troponoid system (Scheme 4;7).
- Subjects
RING formation (Chemistry); AMINO group; REARRANGEMENTS (Chemistry); REACTION mechanisms (Chemistry)
- Publication
Helvetica Chimica Acta, 2008, Vol 91, Issue 2, p187
- ISSN
0018-019X
- Publication type
Article