Synthesis of substituted tetrahydron-1H-carbazol-1-one and analogs via PhI(OCOCF3)2-mediated oxidative C-C bond formation

被引：15
|
作者：
Shi, Hao [1 ]
Guo, Tianjian [1 ]
Zhang-Negrerie, Daisy [1 ]
Du, Yunfei [1 ,2 ]
Zhao, Kang [1 ]
机构：
[1] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin Key Lab Modern Drug Delivery & High Effic, Tianjin 300072, Peoples R China
[2] China & Collaborat Innovat Ctr Chem Sci & Engn Ti, Tianjin 300072, Peoples R China
来源：
TETRAHEDRON | 2014年 / 70卷 / 17期
基金：
中国国家自然科学基金;
关键词：
Hypervalent iodine reagent; Metal-free coupling; Oxidative annulation; C(sp(2))-C(sp(2)) bond formation; Tetrahydro-1H-carbazol-1-one; ACIDS; CYCLIZATION; CONVENIENT;
D O I：
10.1016/j.tet.2014.02.083
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A variety of tetrahydro-1H-carbazol-1-ones and analogs were conveniently synthesized from the reaction of the corresponding 2-(phenylamino)cyclohex-2-enone with hypervalent iodine reagent PhI(OCOCF3)2 (FIFA), through a direct intramolecular oxidative C(sp(2))-C(sp(2)) bond formation. This approach realized the construction of the biologically important tetrahydro-1H-carbazol-1-one and tetrahydrocyclohepta[b]lindol-6(5H)-one skeletons. The mechanism of the process was proposed and briefly discussed. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2753 / 2760
页数：8
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