Synthesis of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one and its derivatives Full article
| Journal |
Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353 |
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| Output data | Year: 2017, Volume: 53, Number: 2, Pages: 186-191 Pages count : 6 DOI: 10.1007/s10593-017-2038-4 | ||||
| Tags | 3-aminopyridin-2(1Н)-one, oxazolo[5,4-b]pyridin-2(1H)-one, Hofmann reaction, intramolecular cyclization | ||||
| Authors |
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| Affiliations |
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Funding (1)
| 1 | Russian Foundation for Basic Research | 15-53-45084 |
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(1Н)-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(1Н)-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 POCl 3 allowed to obtain 5,5'-dimethyl-7,7'-diphenyl-2,2'-bis-(oxazolo[5,4-b]pyridine).
Cite:
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. V.53. N2. P.186-191. DOI: 10.1007/s10593-017-2038-4 WOS Scopus РИНЦ OpenAlex
Synthesis of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one and its derivatives
Chemistry of Heterocyclic Compounds. 2017. V.53. N2. P.186-191. DOI: 10.1007/s10593-017-2038-4 WOS Scopus РИНЦ OpenAlex
Dates:
| Submitted: | Nov 20, 2016 |
| Accepted: | Dec 20, 2016 |
| Published print: | Feb 1, 2017 |
| Published online: | Mar 20, 2017 |
Identifiers:
| Web of science: | WOS:000397339800011 |
| Scopus: | 2-s2.0-85015621932 |
| Elibrary: | 31034936 |
| OpenAlex: | W2597382427 |