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超声辅助由1,4-萘醌和α-氨基缩醛一锅法合成苯并稠合吲哚-4,9-二酮

Ultrasound assisted one-pot synthesis of benzo-fused indole-4, 9-dinones from 1,4-naphthoquinone and α-aminoacetals.

作者信息

Luu Quang H, Guerra Jorge D, Castañeda Cecilio M, Martinez Manuel A, Saunders Jong, Garcia Benjamin A, Gonzales Brenda V, Aidunuthula Anushritha R, Mito Shizue

机构信息

Department of Chemistry, The University of Texas at El Paso, El Paso, TX 79968, USA.

Department of Chemistry, The University of Texas Rio Grande Valley, Edinburg, TX 78539, USA.

出版信息

Tetrahedron Lett. 2016 May 25;57(21):2253-2256. doi: 10.1016/j.tetlet.2016.04.031. Epub 2016 Apr 16.

Abstract

A one-pot synthesis of benzo[]indole-4,9-diones from 1,4-naphthoquinone with α-aminoacetals has been developed. This method provides a straightforward synthesis of benzo[]indole-4,9-diones via intramolecular nucleophilic attack of aminoquinones to aldehydes under mild reaction conditions. The detailed mechanism was also investigated.

摘要

已开发出一种由1,4-萘醌与α-氨基缩醛一锅法合成苯并[ ]吲哚-4,9-二酮的方法。该方法通过氨基醌对醛的分子内亲核进攻,在温和的反应条件下直接合成苯并[ ]吲哚-4,9-二酮。还对详细的反应机理进行了研究。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8ebb/8158052/7243fd4b42a9/nihms803304f1.jpg

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本文引用的文献

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Bexarotene prodrugs: targeting through cleavage by NQO1 (DT-diaphorase).倍他罗汀前药:通过 NQO1(DT-黄递酶)切割进行靶向。
Bioorg Med Chem Lett. 2014 Apr 15;24(8):1944-7. doi: 10.1016/j.bmcl.2014.03.003. Epub 2014 Mar 13.
3
Copper(II)-Mediated Synthesis of Indolequinones from Bromoquinones and Enamines.铜(II)介导的由溴醌和烯胺合成吲哚醌
European J Org Chem. 2013 Apr;2013(11):2179-2187. doi: 10.1002/ejoc.201201597. Epub 2013 Feb 20.
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