One-Step Synthesis of 1,2,5-Trisubstituted Pyrroles by Copper Catalyzed Condensation of 1,4-Diones with Primary Amines

被引:9
作者
Srinivas, Rapelli [1 ]
Thirupathi, Boningari [1 ]
Kumar, J. K. Prashanth [1 ]
Prasad, Avvari N. [1 ]
Reddy, Benjaram M. [1 ]
机构
[1] Indian Inst Chem Technol, Inorgan & Phys Chem Div, Hyderabad 500607, Andhra Pradesh, India
关键词
CuI/C; Heterogeneous catalyst; Paal-Knorr condensation; N-Substituted pyrroles; Solvent-free; ONE-POT SYNTHESIS; HETEROGENEOUS CATALYST; SUBSTITUTED PYRROLES; ACTIVATED CARBON; ACETYLACETONATE; NANOPARTICLES; ADSORPTION; CHEMISTRY; PLATINUM; CHLORIDE;
D O I
10.2174/138527212803520182
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Highly dispersed copper iodide on activated carbon (CuI/C) solid catalyst has been investigated for the Paal-Knorr condensation of gamma-diketones with aliphatic, aromatic and heterocyclic amines under solvent-free conditions; which lead to the formation of N-substituted pyrrole derivatives in excellent yields. This simple experimental procedure combined with easy recovery and reusability of the catalyst is expected to contribute to the progression of a clean and ecofriendly strategy for the synthesis of N-substituted pyrrole derivatives.
引用
收藏
页码:2482 / 2489
页数:8
相关论文
共 48 条
[31]  
Patil MK, 2011, CURR ORG CHEM, V15, P3961
[32]   Conversion of aryl methyl ketimines to 2,5-diarylpyrroles using TiCl4/Et3N [J].
Periasamy, M ;
Srinivas, G ;
Bharathi, P .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :4204-4205
[33]   Antimycobacterial pyrroles:: Synthesis, anti-Mycobacterium tuberculosis activity and QSAR studies [J].
Ragno, R ;
Marshall, GR ;
Di Santo, R ;
Costi, R ;
Massa, S ;
Rompei, R ;
Artico, M .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (06) :1423-1432
[34]   One-Pot Synthesis of N-Substituted Pyrroles Catalyzed by Polystyrene-Supported Aluminum Chloride as a Reusable Heterogeneous Lewis Acid Catalyst [J].
Rahmatpour, Ali ;
Aalaie, Jamal .
HETEROATOM CHEMISTRY, 2011, 22 (01) :85-90
[35]   Microwave mediated facile one-pot synthesis of polyarylpyrroles from but-2-ene- and but-2-yne-1,4-diones [J].
Rao, HSP ;
Jothilingam, S ;
Scheeren, HW .
TETRAHEDRON, 2004, 60 (07) :1625-1630
[36]   Promoted zirconia solid acid catalysts for organic synthesis [J].
Reddy, Benjaram M. ;
Patil, Meghshyam K. .
CURRENT ORGANIC CHEMISTRY, 2008, 12 (02) :118-140
[37]   Organic Syntheses and Transformations Catalyzed by Sulfated Zirconia [J].
Reddy, Benjaram M. ;
Patil, Meghshyam K. .
CHEMICAL REVIEWS, 2009, 109 (06) :2185-2208
[38]   A COMPARISON OF WEAK MOLECULAR ADSORPTION OF ORGANIC-MOLECULES ON CLEAN COPPER AND PLATINUM SURFACES [J].
SEXTON, BA ;
HUGHES, AE .
SURFACE SCIENCE, 1984, 140 (01) :227-248
[39]   Copper Nanoparticles on Charcoal for Multicomponent Catalytic Synthesis of 1,2,3-Triazole Derivatives from Benzyl Halides or Alkyl Halides, Terminal Alkynes and Sodium Azide in Water as a "Green" Solvent [J].
Sharghi, Hashem ;
Khalifeh, Reza ;
Doroodmand, Mohammad Mahdi .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (1-2) :207-218
[40]   Copper(II) acetylacetonate anchored onto an activated carbon as a heterogeneous catalyst for the aziridination of styrene [J].
Silva, AR ;
Figueiredo, JL ;
Freire, C ;
de Castro, B .
CATALYSIS TODAY, 2005, 102 :154-159