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

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

doi:10.1016/j.tetlet.2016.04.031

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

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

Authors

Quang H Luu¹, Jorge D Guerra¹, Cecilio M Castañeda¹, Manuel A Martinez¹, Jong Saunders¹, Benjamin A Garcia², Brenda V Gonzales², Anushritha R Aidunuthula², Shizue Mito^{1

2}

Affiliations

¹ Department of Chemistry, The University of Texas at El Paso, El Paso, TX 79968, USA.
² Department of Chemistry, The University of Texas Rio Grande Valley, Edinburg, TX 78539, USA.

Abstract

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

Keywords: Cyclization; Heterocycles; One-pot reaction; Ultrasound-assisted; p-Indolequinone.

Grants and funding

R25 GM100866/GM/NIGMS NIH HHS/United States