Issue 9, 2016
From the journal:

Organic & Biomolecular Chemistry

Iodine-catalyzed synthesis of dibenzo[b,h][1,6]naphthyridine-11-carboxamides via a domino reaction involving double elimination of hydrogen bromide†

Bin-Bin Feng,a   Lian Lu,a   Chao Lia  and  Xiang-Shan Wang*a  

* Corresponding authors

a School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthesis for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. China
E-mail: xswang1974@yahoo.com

Abstract

An iodine-catalyzed reaction of 2-aminobenzamides and mucobromic acid was described and utilized to synthesize a variety of 6-oxo-5,6-dihydrodibenzo[b,h][1,6]naphthyridine-11-carboxamide derivatives in refluxing THF. As the two bromine atoms in mucobromic acid were found missing in the dibenzonaphthyridine products, a domino-type reaction mechanism involving a double elimination of hydrogen bromide was proposed.

Graphical abstract: Iodine-catalyzed synthesis of dibenzo[b,h][1,6]naphthyridine-11-carboxamides via a domino reaction involving double elimination of hydrogen bromide

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Article information

DOI
https://doi.org/10.1039/C5OB02620B
Article type
Paper
Submitted
21 Dec 2015
Accepted
03 Feb 2016
First published
03 Feb 2016

Org. Biomol. Chem., 2016,14, 2774-2779

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Iodine-catalyzed synthesis of dibenzo[b,h][1,6]naphthyridine-11-carboxamides via a domino reaction involving double elimination of hydrogen bromide

B. Feng, L. Lu, C. Li and X. Wang, Org. Biomol. Chem., 2016, 14, 2774 DOI: 10.1039/C5OB02620B

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