Regioselective synthesis of 3,4,5-trisubstituted 2-aminofurans

被引：15

作者：

Thi Ngoc Tram Huynh ^{[1
,2
]}

Retailleau, Pascal ^{[3
]}

Denhez, Clement ^{[1
]}

Kim Phi Phung Nguyen ^{[2
]}

Guillaume, Dom ^{[1
]}

机构：

[1] Univ Reims, UFR Pharm, CNRS, ICMR,UMR7312, F-51096 Reims, France

[2] Natl Univ Ho Chi Minh City, Univ Sci, Dept Organ Chem, Ho Chi Minh City 748355, Vietnam

[3] CNRS, Inst Chim Subst Nat, UPR2301, F-91190 Gif Sur Yvette, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 28期

关键词：

ONE-POT SYNTHESIS; POLYSUBSTITUTED FURANS; 3-COMPONENT SYNTHESIS; DERIVATIVES; CONSTRUCTION; ISOCYANIDES; CYCLIZATION; MOLECULES; ALDEHYDES; SYSTEMS;

D O I：

10.1039/c4ob01037j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three series of methyl 5-substituted 2-aminofuran-4-keto-3-carboxylates have been prepared following a multicomponent reaction strategy by the addition of an isocyanide to 4-oxo-2-butynoate in the presence of an aldehyde. The cycloaddition regioselectivity is generally high (>95%) but decreases when an electron-rich substituent is located at the butynoate 4-position.

引用

页码：5098 / 5101

页数：4

共 38 条

[1]

Abderhamid A. O., 1981, J PRAKT CHEM, V331, P31

[2] Facile one-pot three-component synthesis of functionalized pyridylfuran-2-amines [J].

Adib, M ;

Sayahi, MH ;

Koloogani, SA ;

Mirzaei, P .

HELVETICA CHIMICA ACTA, 2006, 89 (02) :299-303

[3] FLASH VACUUM PYROLYSIS OF STABILIZED PHOSPHORUS YLIDES .5. SELECTIVE EXTRUSION OF PH(3)PO FROM BETA,GAMMA,BETA-TRIOXO YLIDES TO GIVE DIACYLALKYNES [J].

AITKEN, RA ;

HERION, IL ;

JANOSI, A ;

KARODIA, N ;

RAUT, SV ;

SETH, S ;

SHANNON, IJ ;

SMITH, FC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (17) :2467-2472

[4]

Akritopoulou-Zanze I., 2012, ISOCYANIDE CHEM, P451

[5] Competition of the R3P/DAAD and RNC/DAAD zwitterions in their production and reaction with aromatic carboxylic acids:: A novel binucleophilic system for three-component synthesis of 2-aminofurans [J].

Alizadeh, Abdolali ;

Rostamnia, Sadegh ;

Zhu, Long-Guan .

SYNTHESIS-STUTTGART, 2008, (11) :1788-1792

[6]

Asghari S, 2010, ASIAN J CHEM, V22, P3435

[7] A modified and green methodology for preparation of polysubstituted furans [J].

Azizian, J ;

Mohammadizadeh, MR ;

Mohammadi, AA ;

Karimi, AR .

HETEROATOM CHEMISTRY, 2005, 16 (04) :259-262

[8] An IMDAF Cycloaddition Approach toward the Synthesis of the Lycopodium Alkaloid (±)-Fawcettidine [J].

Boonsompat, Jutatip ;

Padwa, Albert .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08) :2753-2761

[9] Quantitative characterization of the local electrophilicity of organic molecules.: Understanding the regioselectivity on Diels-Alder reactions [J].

Domingo, LR ;

Aurell, MJ ;

Pérez, P ;

Contreras, R .

JOURNAL OF PHYSICAL CHEMISTRY A, 2002, 106 (29) :6871-6875

[10] The chemistry of α-haloketones and their utility in heterocyclic synthesis [J].

Erian, AW ;

Sherif, SM ;

Gaber, HM .

MOLECULES, 2003, 8 (11) :793-865

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