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
收藏
页码：1798 / 1810
页数：13
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