Synthesis, structure and biological activity 3- (arylmethyl) aminopyridine-2 (1 H ) -ones and 1 H -pyrido[2,3-b][1,4]oxazin-2(3 H )-ones
Ivan V. Kulakov
1
,
Zarina T. Shulgau
2
,
Tulegen M Seilkhanov
3
,
Yuriy V. Gatilov
4, 5
,
Alexander S. Fisyuk
6, 7, 8, 9
2
RSE “ National Center for Biotechnology” of the Ministry of Education and Science, 13/5 Kurgalzhynskoe Road, Astana 010000, Kazakhstan
|
3
Sh. Ualikhanov Kokshetau State University, 76 Abaya St., Kokshetau 020000, Kazakhstan
|
6
Department of Organic Chemistry
8
55a Mira Ave 644077 Omsk Russia
|
Publication type: Journal Article
Publication date: 2018-08-01
scimago Q2
wos Q2
SJR: 0.628
CiteScore: 8.0
Impact factor: 4.7
ISSN: 00222860, 18728014
Organic Chemistry
Inorganic Chemistry
Spectroscopy
Analytical Chemistry
Abstract
Reaction of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one with aromatic aldehydes afforded the corresponding Schiff bases, the reduction of which with sodium borohydride led to the formation of 3-(arylmethyl)-6-methyl-4-phenylpyridin-2(1H)-ones. Acylation of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one with chloroacetyl chloride resulted either in the corresponding chloroacetamides or in 1H-pyrido[2,3-b][1,4]oxazin-2(3H)-ones. A possibility to form octahedral complex with calcium chloride was demonstrated by the example of 3-(benzylamino)-6-methyl-4-phenylpyridin-2(1H)-one. Structure of all the prepared compounds was proved by 1H and 13C NMR spectroscopy, as well as single crystal X-ray diffraction method. Among a series of novel compounds, 3-(arylmethyl)-6-methyl-4-phenylpyridin-2(1H)-one derivatives showed antiradical activity against DPPH and ABTS radicals.
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Kulakov I. V. et al. Synthesis, structure and biological activity 3- (arylmethyl) aminopyridine-2 (1 H ) -ones and 1 H -pyrido[2,3-b][1,4]oxazin-2(3 H )-ones // Journal of Molecular Structure. 2018. Vol. 1166. pp. 262-269.
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Kulakov I. V., Palamarchuk I. V., Shulgau Z. T., Seilkhanov T. M., Gatilov Y. V., Fisyuk A. S. Synthesis, structure and biological activity 3- (arylmethyl) aminopyridine-2 (1 H ) -ones and 1 H -pyrido[2,3-b][1,4]oxazin-2(3 H )-ones // Journal of Molecular Structure. 2018. Vol. 1166. pp. 262-269.
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TY - JOUR
DO - 10.1016/j.molstruc.2018.04.036
UR - https://doi.org/10.1016/j.molstruc.2018.04.036
TI - Synthesis, structure and biological activity 3- (arylmethyl) aminopyridine-2 (1 H ) -ones and 1 H -pyrido[2,3-b][1,4]oxazin-2(3 H )-ones
T2 - Journal of Molecular Structure
AU - Kulakov, Ivan V.
AU - Palamarchuk, Irina V
AU - Shulgau, Zarina T.
AU - Seilkhanov, Tulegen M
AU - Gatilov, Yuriy V.
AU - Fisyuk, Alexander S.
PY - 2018
DA - 2018/08/01
PB - Elsevier
SP - 262-269
VL - 1166
SN - 0022-2860
SN - 1872-8014
ER -
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BibTex (up to 50 authors)
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@article{2018_Kulakov,
author = {Ivan V. Kulakov and Irina V Palamarchuk and Zarina T. Shulgau and Tulegen M Seilkhanov and Yuriy V. Gatilov and Alexander S. Fisyuk},
title = {Synthesis, structure and biological activity 3- (arylmethyl) aminopyridine-2 (1 H ) -ones and 1 H -pyrido[2,3-b][1,4]oxazin-2(3 H )-ones},
journal = {Journal of Molecular Structure},
year = {2018},
volume = {1166},
publisher = {Elsevier},
month = {aug},
url = {https://doi.org/10.1016/j.molstruc.2018.04.036},
pages = {262--269},
doi = {10.1016/j.molstruc.2018.04.036}
}