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Synthesis 2018; 50(06): 1350-1358
DOI: 10.1055/s-0036-1589154
paper
© Georg Thieme Verlag Stuttgart · New York

Direct Synthesis of 6H-Chromeno[3,4-b]quinolin-6-ol Derivatives from Substituted 3-Nitro-2H-chromenes and 2-Nitrobenzaldehydes Mediated by Fe/AcOH System

Xushun Qing
School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China   Email: wangcd@yzu.edu.cn
,
Ting Wang
School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China   Email: wangcd@yzu.edu.cn
,
Chenlu Dai
School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China   Email: wangcd@yzu.edu.cn
,
Zhenjie Su
School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China   Email: wangcd@yzu.edu.cn
,
Cunde Wang  *
School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China   Email: wangcd@yzu.edu.cn
› Author AffiliationsNational Natural Science Foundation of China (NNSFC 21173181). The project was funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions and Top-notch Academic Programs Project of Jiangsu Higher Education Institutions.
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Publication History

Received: 18 October 2017

Accepted after revision: 24 November 2017

Publication Date:
20 December 2017 (online)

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Abstract

An efficient iron/acetic acid system-mediated reductive cyclization reaction of substituted 2-aryl-3-nitro-2H-chromenes with substituted 2-nitrobenzaldehydes for the synthesis of 6-aryl-6H-chromeno[3,4-b]quinolines was developed. This reaction involves the sequential reduction, hydrolysis, aldol condensation, intramolecular addition, and the nucleophilic addition of substituted 2-aryl-3-nitro-2H-chromenes with substituted 2-nitrobenzaldehydes to give the corresponding 6H-chromeno[3,4-b]quinolines. This transformation provides a straightforward synthetic protocol for constructing substituted 6H-chromeno[3,4-b]quinoline derivatives. The structures of three typical products were confirmed by X-ray crystallography.

Key words

6-aryl-6H-chromeno[3,4-b]quinolin-6-ol - 2-aryl-3-nitro-2H-chromenes - reductive cyclization reaction - 2-nitrobenzaldehyde - Povarov reaction

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589154.
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