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

被引：12

作者：

Pan, Xuan

Liu, Zhanzhu ^{[1
]}

机构：

[1] Peking Union Med Coll, Inst Mat Med, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 11期

关键词：

TERTIARY-AMINES; N-ARYLATION; POTENT; RECEPTOR; DISCOVERY; ANTAGONISTS; ACCESS; CO2;

D O I：

10.1039/c8qo00275d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 -arylated products of the carbonyl group were also obtained. Preliminary mechanistic studies suggest both 3-aryl-3-benzazepines and -arylated products of the carbonyl group were generated via the rearrangement of nitrogen ylide intermediates.

引用

页码：1798 / 1810

页数：13

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