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1,6-Hydride Transfer-Enabled [6 + 1] Annulation to Access Polycyclic 3,4-Fused Azepinoindoles
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2023-06-01 , DOI: 10.1021/acs.joc.3c00631
Xiao-De An 1 , Zhonglin Wang 1 , Yao-Bin Shen 2 , Bin Qiu 1 , Jian Xiao 1
Affiliation  

A [6 + 1] annulation reaction via cascade 1,6-hydride transfer/cyclization is reported to construct a polycyclic 3,4-fused azepinoindole skeleton. The newly designed 4-amino-indole-3-carbaldehyde is applied as a novel six-atom synthon, interacting with arylamines and malononitrile to achieve the [6 + 1] annulation. Notably, the reaction proceeds smoothly under redox-neutral and metal-free conditions, providing a wide range of azepinoindoles in up to 94% yields, with water as the only byproduct. Besides, the advantage of high step- and atom-economy further highlights the practicality of this methodology.

中文翻译:

1,6-氢化物转移启用的 [6 + 1] 环化以获得多环 3,4-稠合氮杂吲哚

据报道,通过级联 1,6-氢化物转移/环化的 [6 + 1] 环化反应构建了多环 3,4-稠合氮杂吲哚骨架。新设计的4-氨基-吲哚-3-甲醛被用作新型六原子合成子,与芳胺和丙二腈相互作用以实现[6 + 1]环化。值得注意的是,该反应在氧化还原中性和无金属条件下顺利进行,提供了多种氮杂吲哚,产率高达 94%,水是唯一的副产物。此外,高步骤经济性和原子经济性的优势进一步凸显了该方法的实用性。
更新日期:2023-06-01
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