Synthesis of Cyclo[b]fused Carbazoles via SnCl4-Mediated Domino Reaction of 2-Indolylmethylpivalates with Arenes and Heteroarenes

被引：12
|
作者：
Saravanan, Velu [1 ]
Mageshwaran, Thiyagarajan [1 ]
Mohanakrishnan, Arasambattu K. [1 ]
机构：
[1] Univ Madras, Sch Chem, Dept Organ Chem, Guindy Campus, Madras 600025, Tamil Nadu, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 18期
关键词：
TRANSITION-METAL-COMPLEXES; ORGANIC-SYNTHESIS; BIOLOGICAL EVALUATION; DERIVATIVES; ACID; ANTITUMOR; CYCLOADDITION; BENZYLATION; INDOLES; ANALOGS;
D O I：
10.1021/acs.joc.6b01646
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A straightforward synthesis of aryl and heteroaryl-annulated cyclo[b]carbazoles has been developed via SnCl4-mediated one-pot arylation, cyclization and aromatization reaction sequence from 3-acetyl/aroyl-2-pivaloyloxymethylindoles. The starting material is easily accessible from commercially available 2-methylindole via Friedel Crafts acylation, bromination and pivaloylation. Remarkably, electron withdrawing/donating aroyl units including heterocyclic systems are well tolerated in the present domino reaction protocol. Furthermore, this methodology could be extended to the synthesis of dibenzofurocarbazole via bis-annulation of 2,5-bis(2-pivaloyloxymethyl)pyrrole.
引用
收藏
页码：8633 / 8646
页数：14
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