Synthesis of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one and its derivatives

被引：15
|
作者：
Shatsauskas, Anton L. [1 ,2 ]
Abramov, Anton A. [2 ]
Saibulina, Elina R. [2 ]
Palamarchuk, Irina V. [2 ]
Kulakov, Ivan V. [2 ]
Fisyuk, Alexander S. [1 ,2 ]
机构：
[1] Omsk State Tech Univ, 11 Mir Ave, Omsk 644050, Russia
[2] Omsk State Univ, 55a Mir Ave, Omsk 644077, Russia
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2017年 / 53卷 / 02期
基金：
俄罗斯基础研究基金会;
关键词：
aminopyridin-2(1.)-one; oxazolo[5,4-b]pyridin-2(1H)-one; Hofmann reaction; intramolecular cyclization; INTRAMOLECULAR CYCLIZATION; BIOLOGICAL EVALUATION; INHIBITORS; DESIGN;
D O I：
10.1007/s10593-017-2038-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A reaction of 2-cyanoacetamide with benzylideneacetone in DMSO containing potassium tert-butoxide was used to synthesize 3-cyano6-methyl-4-phenylpyridin-2(1.)-one, which was converted by acidic hydrolysis to 6-methyl-2-oxo-4-phenyl-1,2-dihydropyridine-3carboxamide.A Hofmann reaction of this compound in the presence of sodium hypobromite led to 3-amino-5-bromo-6-methyl4-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(1.)-one, which gave azomethine in a reaction with benzaldehyde, while N-acylated derivatives were obtained in reactions with acyl halides. The heating of N1, N2- bis(6-methyl2-oxo-4-phenyl-1,2-dihydropyridin-3-yl)oxalylamidein the presence of POCl3 allowed to obtain 5,5'-dimethyl-7,7'-diphenyl-2,2'-bis( oxazolo[5,4-b] pyridine).
引用
收藏
页码：186 / 191
页数：6
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