An environmentally benign approach for the synthesis of 3,4,5-trisubstituted 2-aminofurans under solvent-free conditions via isocyanide-based multicomponent approach

被引：12

作者：

Shah, Tariq A. ^{[1
]}

Ahmad, Zubair ^{[1
]}

Rath, N. P. ^{[2
,3
]}

Muneer, M. ^{[1
]}

机构：

[1] Aligarh Muslim Univ, Dept Chem, Aligarh 202002, Uttar Pradesh, India

[2] Univ Missouri, Dept Chem & Biochem, St Louis, MO 63121 USA

[3] Univ Missouri, Ctr Nanosci, St Louis, MO 63121 USA

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 24期

基金：

美国国家科学基金会;

关键词：

Multicomponent; Dibenzoylacetylene; 2-Aminofurans; Isocyanide; Solvent-free; ONE-POT SYNTHESIS; ORGANIC-SYNTHESIS; CASCADE REACTIONS; EFFICIENT; FURANS; CHEMISTRY; ALDEHYDES; CATALYST;

D O I：

10.1016/j.tetlet.2016.05.007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient solvent-free procedure for the synthesis of 3,4,5-trisubstituted 2-aminofurans has been developed via a multicomponent strategy by the solid state condensation of finely grounded dibenzoylacetylene and aromatic aldehydes in the presence of isocyanides at room temperature. Clean reaction profile, easy work-up procedure, non-chromatographic purification technique, short reaction times, high yields, and solvent-free reaction conditions are the remarkable advantages of this procedure. Single crystal X-ray diffraction has been established for four structures. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：2638 / 2641

页数：4

共 69 条

[1] 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
Alizadeh, Abdolali
Rostamnia, Sadegh
Zhu, Long-Guan
[J]. SYNTHESIS-STUTTGART, 2008, (11): : 1788 - 1792
[2] Anastas P., 1998, GREEN CHEM THEORY PR
[3] [Anonymous], 2003, GREE CHEM
[4] Pd-assisted multicomponent synthesis of heterocycles
Balme, G
Bossharth, E
Monteiro, N
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) : 4101 - 4111
[5] Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[6] 2-A
[7] An IMDAF Cycloaddition Approach toward the Synthesis of the Lycopodium Alkaloid (±)-Fawcettidine
Boonsompat, Jutatip
Padwa, Albert
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08) : 2753 - 2761
[8] Developments in furan syntheses
Brown, RCD
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (06) : 850 - 852
[9] Rapid Synthesis of 1,3,4,4-Tetrasubstituted β-Lactams from Methyleneaziridines Using a Four-Component Reaction
Cariou, Claire C. A.
Clarkson, Guy J.
Shipman, Michael
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (24) : 9762 - 9764
[10] Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility
Cave, GWV
Raston, CL
Scott, JL
[J]. CHEMICAL COMMUNICATIONS, 2001, (21) : 2159 - 2169

← 1 2 3 4 5 6 7 →