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A New Approach to the Synthesis of Benzo[ c ][1,7]naphthyridin-4(3 H)-ones. / Kulakov, Ivan V.; Shatsauskas, Anton L.; Matsukevich, Mariya V. et al.

In: Synthesis (Germany), Vol. 49, No. 16, 16.08.2017, p. 3700-3709.

Research output: Contribution to journal › Article › peer-review

Harvard

Kulakov, IV, Shatsauskas, AL, Matsukevich, MV, Palamarchuk, IV, Seilkhanov, TM, Gatilov, YV & Fisyuk, AS 2017, 'A New Approach to the Synthesis of Benzo[ c ][1,7]naphthyridin-4(3 H)-ones', Synthesis (Germany), vol. 49, no. 16, pp. 3700-3709. https://doi.org/10.1055/s-0036-1590470

APA

Kulakov, I. V., Shatsauskas, A. L., Matsukevich, M. V., Palamarchuk, I. V., Seilkhanov, T. M., Gatilov, Y. V., & Fisyuk, A. S. (2017). A New Approach to the Synthesis of Benzo[ c ][1,7]naphthyridin-4(3 H)-ones. Synthesis (Germany), 49(16), 3700-3709. https://doi.org/10.1055/s-0036-1590470

Vancouver

Kulakov IV, Shatsauskas AL, Matsukevich MV, Palamarchuk IV, Seilkhanov TM, Gatilov YV et al. A New Approach to the Synthesis of Benzo[ c ][1,7]naphthyridin-4(3 H)-ones. Synthesis (Germany). 2017 Aug 16;49(16):3700-3709. doi: 10.1055/s-0036-1590470

Author

Kulakov, Ivan V. ; Shatsauskas, Anton L. ; Matsukevich, Mariya V. et al. / A New Approach to the Synthesis of Benzo[ c ][1,7]naphthyridin-4(3 H)-ones. In: Synthesis (Germany). 2017 ; Vol. 49, No. 16. pp. 3700-3709.

BibTeX

@article{9feae3c60230424a9774b3049fb5a7b7,
title = "A New Approach to the Synthesis of Benzo[ c ][1,7]naphthyridin-4(3 H)-ones",
abstract = "A simple and efficient approach has been developed for the synthesis of previously inaccessible 6-arylbenzo[ c ][1,7]naphthyridin-4(3 H)-ones, which is based on the interaction of 3-amino-6-methyl-4-arylpyridin-2(1 H)-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(3 H)-ones, which are oxidized by atmospheric oxygen to give 3-amino-6-methyl-4-arylpyridin-2(1 H)-ones as the final products.",
keywords = "intramolecular cyclization, naphthyridines, Pictet-Spengler reaction, pyridines, X-ray structural analysis",
author = "Kulakov, {Ivan V.} and Shatsauskas, {Anton L.} and Matsukevich, {Mariya V.} and Palamarchuk, {Irina V.} and Seilkhanov, {Tulegen M.} and Gatilov, {Yuriy V.} and Fisyuk, {Alexander S.}",
year = "2017",
month = aug,
day = "16",
doi = "10.1055/s-0036-1590470",
language = "English",
volume = "49",
pages = "3700--3709",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "16",

}

RIS

TY - JOUR

T1 - A New Approach to the Synthesis of Benzo[ c ][1,7]naphthyridin-4(3 H)-ones

AU - Kulakov, Ivan V.

AU - Shatsauskas, Anton L.

AU - Matsukevich, Mariya V.

AU - Palamarchuk, Irina V.

AU - Seilkhanov, Tulegen M.

AU - Gatilov, Yuriy V.

AU - Fisyuk, Alexander S.

PY - 2017/8/16

Y1 - 2017/8/16

N2 - A simple and efficient approach has been developed for the synthesis of previously inaccessible 6-arylbenzo[ c ][1,7]naphthyridin-4(3 H)-ones, which is based on the interaction of 3-amino-6-methyl-4-arylpyridin-2(1 H)-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(3 H)-ones, which are oxidized by atmospheric oxygen to give 3-amino-6-methyl-4-arylpyridin-2(1 H)-ones as the final products.

AB - A simple and efficient approach has been developed for the synthesis of previously inaccessible 6-arylbenzo[ c ][1,7]naphthyridin-4(3 H)-ones, which is based on the interaction of 3-amino-6-methyl-4-arylpyridin-2(1 H)-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(3 H)-ones, which are oxidized by atmospheric oxygen to give 3-amino-6-methyl-4-arylpyridin-2(1 H)-ones as the final products.

KW - intramolecular cyclization

KW - naphthyridines

KW - Pictet-Spengler reaction

KW - pyridines

KW - X-ray structural analysis

UR - http://www.scopus.com/inward/record.url?scp=85020453598&partnerID=8YFLogxK

U2 - 10.1055/s-0036-1590470

DO - 10.1055/s-0036-1590470

M3 - Article

AN - SCOPUS:85020453598

VL - 49

SP - 3700

EP - 3709

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 16

ER -

ID: 10184869