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

页码：186 / 191

页数：6

共 50 条

[31] Synthesis of 1-benzyloxypyrazin-2(1H)-one derivatives
Anh Hung Mai
Pawar, Sonalika
De Borggraeve, Wim M.
TETRAHEDRON LETTERS, 2014, 55 (33) : 4664 - 4666
[32] SYNTHESIS OF 1'-ADAMANTYL-4-HYDROXY-N-METHYL-3-CHINOLIN-2(1H)-ONE CARBOXAMIDE
REISCH, J
IDING, M
PHARMAZIE, 1993, 48 (08): : 620 - 620
[33] STRUCTURES OF 2 ACTIVE INOTROPIC CARDIAC AGENTS - MILRINONE [5-CYANO-2-METHYL-(3,4'-BIPYRIDIN)-6(1H)-ONE] (I) AND AMRINONE [5-AMINO-(3,4'-BIPYRIDIN)-6(1H)-ONE] (II)
CODY, V
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1987, 43 : 1325 - 1328
[34] ON THE SYNTHESIS OF 3-AMINO-4-ARYL-2(1H)-QUINOLINONES
BAHR, F
USBECK, H
PHARMAZIE, 1981, 36 (10): : 668 - 671
[35] Formation of 3,4,5,6-tetrahydroquinazolin-2(1H)-one derivatives in reaction of 4-aryl-6-methyl-3,4-dihydro-pyrimidin-2(1H)-ones with chalcones
M. A. Kolosov
O. G. Kulyk
O. I. Starchenko
V. D. Orlov
Chemistry of Heterocyclic Compounds, 2013, 49 : 1166 - 1171
[36] Formation of 3,4,5,6-tetrahydroquinazolin-2(1H)-one derivatives in reaction of 4-aryl-6-methyl-3,4-dihydro-pyrimidin-2(1H)-ones with chalcones
Kolosov, M. A.
Kulyk, O. G.
Starchenko, O. I.
Orlov, V. D.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2013, 49 (08) : 1166 - 1171
[37] NOVEL REACTION OF CARBON SUBOXIDE - SYNTHESIS OF 6-AMINO-4-HYDROXY-2(1H)-PYRIDONE DERIVATIVES
BONSIGNORE, L
COCCO, MT
LOY, G
ONNIS, V
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (01) : 237 - 239
[38] Transformations of 3-nitropyridin-4(1H)-one and 1-Methyl-3-nitropyridin-4(1H)-one in reaction with hydrazine
N. N. Smolyar
Russian Journal of Organic Chemistry, 2010, 46 : 122 - 125
[39] Transformations of 3-nitropyridin-4(1H)-one and 1-Methyl-3-nitropyridin-4(1H)-one in reaction with hydrazine
Smolyar, N. N.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (01) : 122 - 125
[40] Pyridone Functionalization: Regioselective Deprotonation of 6-Methylpyridin-2(1H)- and-4(1H)-one Derivatives
Ropero, Beatriz P. Fernandez Diaz
Elsegood, Mark R. J.
Fairley, Gary
Pritchard, Gareth J.
Weaver, George W.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (31) : 5238 - 5242

← 1 2 3 4 5 →