Synthesis of (macro) heterocycles by consecutive/repetitive isocyanide-based multicomponent reactions

被引：21

作者：

Barreto, Angelica de Fatima S. ^{[1
]}

Andrade, Carlos Kleber Z. ^{[1
]}

机构：

[1] Univ Brasilia, Inst Quim, Lab Quim Metodol & Organ Sintet LaQMOS, BR-70910970 Brasilia, DF, Brazil

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 15卷

关键词：

consecutive/repetitive multicomponent reactions; isocyanide; isocyanide-based multicomponent reactions; (macro) heterocycles; Passerini reaction; Ugi reaction; BIFUNCTIONAL BUILDING-BLOCKS; HYBRID MACROCYCLES; UGI; MACROCYCLIZATIONS; TETRAZOLES; CHEMISTRY; CAGES; MIBS;

D O I：

10.3762/bjoc.15.88

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Isocyanide-based multicomponent reactions are a versatile tool in the synthesis of heterocycles. This review describes recently developed approaches based on the combination of consecutive or repetitive isocyanide-based multicomponent reactions for the synthesis of structurally diverse heterocycles. These strategies have also allowed the synthesis of a plethora of macroheterocycles in a reduced number of steps.

引用

页码：906 / 930

页数：25

共 51 条

[1] Artificial Macrocycles by Ugi Reaction and Passerini Ring Closure [J].

Abdelraheem, Eman M. M. ;

Kurpiewska, Katarzyna ;

Kalinowska-Tluscik, Justyna ;

Domling, Alexander .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19) :8789-8795

[2] Rapid Assembly of Polyfunctional Structures Using a One-Pot Five- and Six-Component Sequential Groebke-Blackburn/Ugi/Passerini Process [J].

Al-Tel, Taleb H. ;

Al-Qawasmeh, Raed A. ;

Voelter, Wolfgang .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (29) :5586-5593

[3]

Ameta K L., 2017, Multicomponent Reactions: Synthesis of Bioactive Heterocycles

[4] Applying green processes and techniques to simplify reaction work-ups [J].

Andrade, Carlos Kleber Z. ;

Dar, Abdul Rouf .

TETRAHEDRON, 2016, 72 (47) :7375-7391

[5]

[Anonymous], 1850, LIEBIGS ANN CHEM, DOI [10.1002/jlac.18500750103, DOI 10.1002/JLAC.18500750103]

[6] Microwave-mediated synthesis of a cyclic heptapeptoid through consecutive Ugi reactions [J].

Barreto, Angelica de Fatima S. ;

Andrade, Carlos Kleber Z. .

TETRAHEDRON, 2018, 74 (48) :6861-6865

[7] Consecutive hydrazino-Ugi-azide reactions: synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles [J].

Barreto, Angelica de Fatima S. ;

dos Santos, Veronica Alves ;

Andrade, Carlos Kleber Z. .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 :2596-2602

[8] Consecutive isocyanide-based multicomponent reactions: synthesis of cyclic pentadepsipeptoids [J].

Barreto, Angelica de Fatima S. ;

Vercillo, Otilie E. ;

Wessjohann, Ludger A. ;

Andrade, Carlos Kleber Z. .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 :1017-1022

[9] Fast and efficient microwave-assisted synthesis of functionalized peptoids via Ugi reactions [J].

Barreto, Angelica de Fatima S. ;

Vercillo, Otilie E. ;

Birkett, Mike A. ;

Caulfield, John C. ;

Wessjohann, Ludger A. ;

Andrade, Carlos Kleber Z. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (14) :5024-5027

[10] Higher-order multicomponent reactions: beyond four reactants [J].

Brauch, Sebastian ;

van Berkel, Sander S. ;

Westermann, Bernhard .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (12) :4948-4962

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