Approach to the Library of Fused Pyridine-4-carboxylic Acids by Combes-Type Reaction of Acyl Pyruvates and Electron-Rich Amino Heterocycles

被引：25

作者：

Volochnyuk, Dmitriy M. ^{[1
,3
]}

Ryabukhin, Sergey V. ^{[1
,2
]}

Plaskon, Andrey S. ^{[1
,2
]}

Dmytriv, Yuri V. ^{[1
,3
]}

Grygorenko, Oleksandr O. ^{[1
,2
]}

Mykhailiuk, Pavel K. ^{[1
,2
]}

Krotko, Dmitriy G. ^{[1
]}

Pushechnikov, Alexei ^{[1
]}

Tolmachev, Andrey A. ^{[1
,2
]}

机构：

[1] Enamine Ltd, UA-01103 Kiev, Ukraine

[2] Kyiv Natl Taras Shevchenko Univ, Dept Chem, UA-01033 Kiev, Ukraine

[3] Natl Acad Sci Ukraine, Inst Organ Chem, UA-02660 Kiev, Ukraine

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2010年 / 12卷 / 04期

关键词：

RECEPTOR ANTAGONISTS; COMBINATORIAL CHEMISTRY; PRACTICAL SYNTHESIS; CLINICAL CANDIDATE; DISCOVERY; BREQUINAR; 5-AMINOPYRAZOLES; IDENTIFICATION; DERIVATIVES; INHIBITORS;

D O I：

10.1021/cc100040q

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A library of fused pyridine-4-carboxylic acids (including pyrazolo[3,4-b]pyridines, isoxazolo[5,4-b]pyridines, furo[2,3-b]pyridines, thieno[2,3-b]pyridines, and pyrido[2,3-d]pyrimidines) was generated by Combes-type reaction of acyl pyruvates and electron-rich amino heterocycles followed by hydrolysis of the ester. The library members were also demonstrated to undergo the standard combinatorial transformations including amide coupling and esterification, as well as less common heterocyclizations to 1,2,4-triazoles and 1,2,4-oxadiazoles.

引用

页码：510 / 517

页数：8

共 4 条

[1] REACTIONS OF ELECTRON-RICH HETEROCYCLES WITH DERIVATIVES OF CARBOXYLIC ORTHO ACIDS .6. REACTION-PATHWAYS AND SYNTHETIC APPLICATIONS OF 3-INDOLYL-METHYL-ETHOXYCARBENIUM TETRAFLUOROBORATES
PFEUFFER, L
MULLER, J
PINDUR, U
CHIMIA, 1985, 39 (05) : 143 - 144
[2] REACTIONS OF ELECTRON-RICH HETEROCYCLES WITH DERIVATIVES OF CARBOXYLIC ORTHO ACIDS .4. REGIOSELECTIVE LEWIS ACID-MEDIATED ELECTROPHILE SUBSTITUTION OF METHYLINDOLES WITH ETHYL ORTHOFORMATE AND ETHYL TRITHIOORTHOFORMATE
MULLER, J
PFEUFFER, L
PINDUR, U
MONATSHEFTE FUR CHEMIE, 1985, 116 (03): : 365 - 370
[3] Cycloaddition reaction of 2-azadienes derived from β-amino acids with electron-rich and electron-deficient alkenes and carbonyl compounds.: Synthesis of pyridine and 1,3-oxazine derivatives
Palacios, F
Herrán, E
Rubiales, G
Ezpeleta, JM
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07): : 2131 - 2135
[4] REGIOSELECTIVE, MILD ACYLATION OF 2-METHYLINDOLE WITH DIKOXYCARBENIUM AND TRIALKOXYCARBENIUM TETRAFLUOROBORATES - A SIMPLE PROCEDURE FOR DERIVING 3-ACYL-2-METHYL-INDOLES AND 3-METHOXYCARBONYL-2-METHYLINDOLE - REACTIONS OF ELECTRON-RICH HETEROCYCLES WITH DERIVATIVES OF CARBOXYLIC ORTHO ACIDS .7.
PINDUR, U
FLO, C
MONATSHEFTE FUR CHEMIE, 1986, 117 (03): : 375 - 383

← 1 →