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Synthesis 2017; 49(16): 3700-3709
DOI: 10.1055/s-0036-1590470
DOI: 10.1055/s-0036-1590470
paper
A New Approach to the Synthesis of Benzo[c][1,7]naphthyridin-4(3H)-ones
Authors
This work was supported by the Ministry of Education and Science of the Russian Federation (project number 4.1657.2017/4.6).
Further Information
Publication History
Received: 26 February 2017
Accepted after revision: 22 April 2017
Publication Date:
07 June 2017 (online)
Abstract
A simple and efficient approach has been developed for the synthesis of previously inaccessible 6-arylbenzo[c][1,7]naphthyridin-4(3H)-ones, which is based on the interaction of 3-amino-6-methyl-4-arylpyridin-2(1H)-ones and aromatic aldehydes in a strong acidic media (trifluoroacetic, phosphorous or polyphosphorous acids) under heating. The initial imine derivatives undergo Pictet–Spengler condensation to form intermediate 6-aryl-5,6-dihydrobenzo[c]-1,7-naphthyridin-4(3H)-ones, which are oxidized by atmospheric oxygen to give 3-amino-6-methyl-4-arylpyridin-2(1H)-ones as the final products.
Key words
naphthyridines - pyridines - Pictet–Spengler reaction - intramolecular cyclization - X-ray structural analysisSupporting Information
- Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1590470.
- Supporting Information (PDF) (opens in new window)
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