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Synthesis 2012; 44(24): 3765-3782
DOI: 10.1055/s-0032-1316808
DOI: 10.1055/s-0032-1316808
paper
Stereoselective Synthesis of Novel 2-Alkenyl-2,3,4,5-tetrahydro-1,4-epoxy-1-benzazepines and 2-Alkenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-4-ols
Further Information
Publication History
Received: 13 August 2012
Accepted after revision: 23 October 2012
Publication Date:
08 November 2012 (online)
Abstract
New series of polyfunctionalized 2,3,4,5-tetrahydro-1,4-epoxy-1-benzazepines and 2,3,4,5-tetrahydro-1H-1-benzazepin-4-ols substituted at C2 with 2-methylprop-1-enyl, (E)-styryl, and (E)-pent-1-enyl were synthesized starting from the corresponding N-alkenyl-substituted [prenyl, trans-cinnamyl, (E)-hex-2-enyl] 2-allylanilines by a three-step sequence consisting of selective oxidation of aromatic secondary amines, intramolecular nitrone–olefin 1,3-dipolar cycloaddition, and reductive cleavage. The intramolecular 1,3-dipolar cycloaddition is stereoselective favoring the exo-cycloadducts (ratio exo/endo 2–3:1). The stereochemistry was determined by exhaustive NMR analysis and X-ray diffraction.
Key words
1,3-dipolar cycloaddition - 2,3,4,5-tetrahydro-1,4-epoxy-1-benzazepines - 2,3,4,5-tetrahydro-1H-1-benzazepin-4-ols - reductive cleavage - nitrogen heterocyclesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
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