Synthesis of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one and its derivatives
Publication type: Journal Article
Publication date: 2017-02-01
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
A reaction of 2-cyanoacetamide with benzylideneacetone in DMSO containing potassium tert-butoxide was used to synthesize 3-cyano-6-methyl-4-phenylpyridin-2(1H)-one, which was converted by acidic hydrolysis to 6-methyl-2-oxo-4-phenyl-1,2-dihydropyridine-3-carboxamide. A Hofmann reaction of this compound in the presence of sodium hypobromite led to 3-amino-5-bromo-6-methyl-4-phenylpyridin-2(1H)-one, while its treatment with calcium hypochlorite produced 5-methyl-7-phenyloxazolo[5,4-b]pyridin-2(1H)-one. The latter compound was converted by heating with alkali to 3-amino-6-methyl-4-phenylpyridin-2(1H)-one, which gave azomethine in a reaction with benzaldehyde, while N-acylated derivatives were obtained in reactions with acyl halides. The heating of N 1,N 2-bis(6-methyl-2-oxo-4-phenyl-1,2-dihydropyridin-3-yl)oxalylamide in the presence of POCl3 allowed to obtain 5,5'-dimethyl-7,7'-diphenyl-2,2'-bis-(oxazolo[5,4-b]pyridine).
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16
Total citations:
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Citations from 2024:
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(12%)
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Shatsauskas A. L. et al. Synthesis of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one and its derivatives // Chemistry of Heterocyclic Compounds. 2017. Vol. 53. No. 2. pp. 186-191.
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Shatsauskas A. L., Abramov A. A., Saibulina E. R., Palamarchuk I. V., Kulakov I. V., Fisyuk A. S. Synthesis of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one and its derivatives // Chemistry of Heterocyclic Compounds. 2017. Vol. 53. No. 2. pp. 186-191.
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RIS
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TY - JOUR
DO - 10.1007/s10593-017-2038-4
UR - https://doi.org/10.1007/s10593-017-2038-4
TI - Synthesis of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one and its derivatives
T2 - Chemistry of Heterocyclic Compounds
AU - Shatsauskas, Anton L.
AU - Abramov, Anton A.
AU - Saibulina, Elina R
AU - Palamarchuk, Irina V
AU - Kulakov, Ivan V
AU - Fisyuk, Alexander S.
PY - 2017
DA - 2017/02/01
PB - Springer Nature
SP - 186-191
IS - 2
VL - 53
SN - 0009-3122
SN - 1573-8353
ER -
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BibTex (up to 50 authors)
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@article{2017_Shatsauskas,
author = {Anton L. Shatsauskas and Anton A. Abramov and Elina R Saibulina and Irina V Palamarchuk and Ivan V Kulakov and Alexander S. Fisyuk},
title = {Synthesis of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one and its derivatives},
journal = {Chemistry of Heterocyclic Compounds},
year = {2017},
volume = {53},
publisher = {Springer Nature},
month = {feb},
url = {https://doi.org/10.1007/s10593-017-2038-4},
number = {2},
pages = {186--191},
doi = {10.1007/s10593-017-2038-4}
}
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MLA
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Shatsauskas, Anton L., et al. “Synthesis of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one and its derivatives.” Chemistry of Heterocyclic Compounds, vol. 53, no. 2, Feb. 2017, pp. 186-191. https://doi.org/10.1007/s10593-017-2038-4.