Synthesis of imidazo[1,5-a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes

被引：8

作者：

Aksenov, Dmitrii A. ^{[1
]}

Arutiunov, Nikolai A. ^{[1
]}

Maliuga, Vladimir V. ^{[1
]}

Aksenov, Alexander, V ^{[1
]}

Rubin, Michael ^{[1
,2
]}

机构：

[1] North Caucasus Fed Univ, Dept Chem, 1a Pushkin St, Stavropol 355017, Russia

[2] Univ Kansas, Dept Chem, 1567 Irving Hill Rd, Lawrence, KS 66045 USA

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 16卷

基金：

俄罗斯基础研究基金会;

关键词：

cyclization; heterocycles; imidazo[1,5-a]pyridines; nitroalkanes; polyphosphoric acid; ONE-POT SYNTHESIS; IMIDAZOACRIDINONE C-1311; EFFICIENT SYNTHESIS; FUSED HETEROCYCLES; MARINE SPONGE; DERIVATIVES; INHIBITORS; APOPTOSIS; BENZOXAZOLES; CYCLIZATION;

D O I：

10.3762/bjoc.16.239

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Imidazo[1,5-a]pyridines were efficiently prepared via the cyclization of 2-picolylamines with nitroalkanes electrophilically activated in the presence of phosphorous acid in polyphosphoric acid (PPA) medium.

引用

页码：2903 / 2910

页数：8

共 54 条

[1] Electrophilically activated nitroalkanes in reaction with aliphatic diamines en route to imidazolines [J].

Aksenov, Alexander, V ;

Aksenov, Nicolai A. ;

Arutiunov, Nikolai A. ;

Malyuga, Vladimir V. ;

Ovcharov, Sergey N. ;

Rubin, Michael .

RSC ADVANCES, 2019, 9 (67) :39458-39465

[2] Electrophilic activation of nitroalkanes in efficient synthesis of 1,3,4-oxadiazoles [J].

Aksenov, Alexander V. ;

Khamraev, Vladislav ;

Aksenov, Nicolai A. ;

Kirilov, Nikita K. ;

Domenyuk, Dmitriy A. ;

Zelensky, Vladimir A. ;

Rubin, Michael .

RSC ADVANCES, 2019, 9 (12) :6636-6642

[3] Dual role of polyphosphoric acid-activated nitroalkanes in oxidative peri-annulations: efficient synthesis of 1,3,6,8-tetraazapyrenes [J].

Aksenov, Alexander V. ;

Ovcharov, Dmitrii S. ;

Aksenov, Nicolai A. ;

Aksenov, Dmitrii A. ;

Nadein, Oleg N. ;

Rubin, Michael .

RSC ADVANCES, 2017, 7 (48) :29927-29932

[4] Rational design of an efficient one-pot synthesis of 6H-pyrrolo[2,3,4-gh] perimidines in polyphosphoric acid [J].

Aksenov, Alexander V. ;

Aksenov, Nicolai A. ;

Ovcharov, Dmitrii S. ;

Aksenov, Dmitrii A. ;

Griaznov, Georgii ;

Voskressensky, Leonid G. ;

Rubin, Michael .

RSC ADVANCES, 2016, 6 (85) :82425-82431

[5] Direct metal-free synthesis of diarylamines from 2-nitropropane via the twofold C-H functionalization of arenes [J].

Aksenov, Alexander V. ;

Aksenov, Nicolai A. ;

Orazova, Naila A. ;

Aksenov, Dmitrii A. ;

Dmitriev, Maksim V. ;

Rubin, Michael .

RSC ADVANCES, 2015, 5 (103) :84849-84855

[6] Benzimidazoles and benzoxazoles via the nucleophilic addition of anilines to nitroalkanes [J].

Aksenov, Alexander V. ;

Smirnov, Alexander N. ;

Aksenov, Nicolai A. ;

Bijieva, Asiyat S. ;

Aksenova, Inna V. ;

Rubin, Michael .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (14) :4289-4295

[7] Nitroethane in Polyphosphoric Acid: A New Reagent for Acetamidation and Amination of Aromatic Compounds [J].

Aksenov, Alexander V. ;

Aksenov, Nicolai A. ;

Nadein, Oleg N. ;

Aksenova, Inna V. .

SYNLETT, 2010, (17) :2628-2630

[8] Preparation of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles via chemoselective cyclocondensation of electrophilically activated nitroalkanes to (thio)semicarbazides or thiohydrazides [J].

Aksenov, Nicolai A. ;

Arutiunov, Nikolai A. ;

Kirillov, Nikita K. ;

Aksenov, Dmitrii A. ;

Aksenov, Alexander V. ;

Rubin, Michael .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (08) :1067-1072

[9] Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity [J].

Aksenov, Nicolai A. ;

Aksenov, Alexander, V ;

Kirilov, Nikita K. ;

Arutiunov, Nikolai A. ;

Aksenov, Dmitrii A. ;

Maslivetc, Vladimir ;

Zhao, Zhenze ;

Du, Liqin ;

Rubin, Michael ;

Kornienko, Alexander .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (34) :6651-6664

[10] One-pot synthesis of benzoxazoles via the metal-free ortho-C-H functionalization of phenols with nitroalkanes [J].

Aksenov, Nicolai A. ;

Aksenov, Alexander V. ;

Nadein, Oleg N. ;

Aksenov, Dmitrii A. ;

Smirnov, Alexander N. ;

Rubin, Michael .

RSC ADVANCES, 2015, 5 (88) :71620-71626

← 1 2 3 4 5 6 →