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

Xuan Pan; Zhanzhu Liu

doi:10.1039/C8QO00275D

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

Xuan Pan^a and Zhanzhu Liu*^a

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* Corresponding authors

^a State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, P. R. China
E-mail: liuzhanzhu@imm.ac.cn

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.

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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

Citation: 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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Organic Chemistry Frontiers

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

Abstract

Supplementary files

Publication details

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

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