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Issue 11, 2018
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Synthesis of 3-aryl-3-benzazepines via aryne [1,2] Stevens rearrangement of 1,2,3,4-tetrahydroisoquinolines

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Abstract

An efficient method for the synthesis of 3-aryl-3-benzazepines via aryne induced [1,2] Stevens rearrangement of 1,2,3,4-tetrahydroisoquinolines is described. This approach provided straightforward access to 3-aryl-3-benzazepines in moderate to good yields under transition-metal-free and strong-base-free conditions. Temperature-dependent α-arylated products of the carbonyl group were also obtained. Preliminary mechanistic studies suggest both 3-aryl-3-benzazepines and α-arylated products of the carbonyl group were generated via the rearrangement of nitrogen ylide intermediates.

Graphical abstract: Synthesis of 3-aryl-3-benzazepines via aryne [1,2] Stevens rearrangement of 1,2,3,4-tetrahydroisoquinolines

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Publication details

The article was received on 13 Mar 2018, accepted on 12 Apr 2018 and first published on 13 Apr 2018


Article type: Research Article
DOI: 10.1039/C8QO00275D
Org. Chem. Front., 2018,5, 1798-1810

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    Synthesis of 3-aryl-3-benzazepines via aryne [1,2] Stevens rearrangement of 1,2,3,4-tetrahydroisoquinolines

    X. Pan and Z. Liu, Org. Chem. Front., 2018, 5, 1798
    DOI: 10.1039/C8QO00275D

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