Synthesis of Cyclo[b]fused Carbazoles via SnCl4-Mediated Domino Reaction of 2-Indolylmethylpivalates with Arenes and Heteroarenes.
Synthesis of Cyclo[b]fused Carbazoles via SnCl4-Mediated Domino Reaction of 2-Indolylmethylpivalates with Arenes and Heteroarenes.
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DOI：
10.1021/acs.joc.6b01646
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发表时间：
2016-09
期刊：
影响因子：
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通讯作者：
V. Saravanan;Thiyagarajan Mageshwaran;A. Mohanakrishnan
中科院分区：
文献类型：
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作者：
V. Saravanan;Thiyagarajan Mageshwaran;A. Mohanakrishnan
通过SnCl 4介导的一锅法芳基化、环化和芳构化反应序列，从3-乙酰基/芳酰基-2-新戊酰氧甲基吲哚直接合成了芳基和杂芳基环的环[B]咔唑。起始材料可通过Friedel-Crafts酰化、溴化和新戊酰化从市售2-甲基吲哚容易地获得。值得注意的是，包括杂环系统的吸电子/供电子芳酰基单元在本多米诺反应方案中耐受良好。此外，该方法可以扩展到通过2，5-二（2-新戊酰氧基甲基）吡咯的双环化合成二苯并呋喃并咔唑。
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.