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Synthesis 2017; 49(16): 3700-3709
DOI: 10.1055/s-0036-1590470
paper
© Georg Thieme Verlag Stuttgart · New York

A New Approach to the Synthesis of Benzo[c][1,7]naphthyridin-4(3H)-ones

Ivan V. Kulakov
a   Department of Organic Chemistry, Omsk F.M. Dostoevsky State University, 55a Mira Ave, 644077 Omsk, Russian Federation   Email: fisyuk@chemomsu.ru
,
Anton L. Shatsauskas
b   Laboratory of New Organic Materials, Omsk State Technical University, 11 Mira Ave, 644050 Omsk, Russian Federation
,
Mariya V. Matsukevich
a   Department of Organic Chemistry, Omsk F.M. Dostoevsky State University, 55a Mira Ave, 644077 Omsk, Russian Federation   Email: fisyuk@chemomsu.ru
,
Irina V. Palamarchuk
с   Sh. Ualikhanov Kokshetau State University, 76 Abaya St., Kokshetau 020000, Kazakhstan
,
Tulegen M. Seilkhanov
a   Department of Organic Chemistry, Omsk F.M. Dostoevsky State University, 55a Mira Ave, 644077 Omsk, Russian Federation   Email: fisyuk@chemomsu.ru
,
Yuriy V. Gatilov
d   N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Science, 9 Akademika Lavrientieva Ave., Novosibirsk 630090, Russian Federation
e   Novosibirsk State University, 2 Pirogov St., Novosibirsk 630090, Russian Federation
,
Alexander S. Fisyuk*
a   Department of Organic Chemistry, Omsk F.M. Dostoevsky State University, 55a Mira Ave, 644077 Omsk, Russian Federation   Email: fisyuk@chemomsu.ru
b   Laboratory of New Organic Materials, Omsk State Technical University, 11 Mira Ave, 644050 Omsk, Russian Federation
› Author AffiliationsThis 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)

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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 analysis

Supporting Information

    Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1590470.
  • Supporting Information
 

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