Supported copper triflate as an efficient catalytic system for the synthesis of highly functionalized 2-naphthol Mannich bases under solvent free condition

被引:45
作者
Dindulkar, Someshwar D. [1 ]
Puranik, Vedavati G. [2 ]
Jeong, Yeon Tae [1 ]
机构
[1] Pukyong Natl Univ, Dept Image Sci & Engn, Pusan 608737, South Korea
[2] Natl Chem Lab, Ctr Mat Characterizat, Pune 400008, Maharashtra, India
关键词
Three-component coupling; Betti bases; Supported copper triflate; Single-crystal XRD; Solvent-free; DOMINO MULTICOMPONENT REACTION; BETTI-BASE; DERIVATIVES; WATER; POT;
D O I
10.1016/j.tetlet.2012.06.022
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Various heterogeneous catalysts (Lewis acid) have been prepared and screened for the synthesis of Betti bases in an attempt to reduce the environmental hazards associated with the conventional homogeneous Lewis acid system. And we found especially Cu(OTf)(2)center dot SiO2 catalyzes the three-component coupling of aldehyde, 2-naphthol, and alicyclic amine to generate Betti base with high efficiency under neat conditions without additional co-catalyst or additive in air. The reaction is not sensitive to water and occurs smoothly in water as well. (c) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4376 / 4380
页数:5
相关论文
共 41 条
[1]   Solvent free thioacetalization of carbonyl compounds catalyzed by Cu(OTf)2-SiO2 [J].
Anand, RV ;
Saravanan, P ;
Singh, VK .
SYNLETT, 1999, (04) :415-416
[2]   Multiple-component condensation strategies for combinatorial library synthesis [J].
Armstrong, RW ;
Combs, AP ;
Tempest, PA ;
Brown, SD ;
Keating, TA .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :123-131
[3]   A green one-pot multicomponent synthesis of 4H-pyrans and polysubstituted aniline derivatives of biological, pharmacological, and optical applications using silica nanoparticles as reusable catalyst [J].
Banerjee, Subhash ;
Horn, Alissa ;
Khatri, Hari ;
Sereda, Grigoriy .
TETRAHEDRON LETTERS, 2011, 52 (16) :1878-1881
[4]  
Betti M., 1941, Org Synth Coll, V1, P381
[5]  
Betti M., 1900, Gazz. Chim. Ital, VII, P301
[6]   Environmentally friendly solvent-free processes: Novel dual catalyst system in Henry reaction [J].
Bhattacharya, A ;
Purohit, VC ;
Rinaldi, F .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (03) :254-258
[7]   The Betti base: the awakening of a sleeping beauty [J].
Cardellicchio, Cosimo ;
Capozzi, Maria Annunziata M. ;
Naso, Francesco .
TETRAHEDRON-ASYMMETRY, 2010, 21 (05) :507-517
[8]   OXYTOCIC ACTIVITY OF BASIC (AMINOMETHYL) DERIVATIVES OF PHENOLS AND RELATED COMPOUNDS [J].
COHEN, A ;
HALL, RA ;
HEATHBROWN, B ;
PARKES, MW ;
REES, AH .
BRITISH JOURNAL OF PHARMACOLOGY AND CHEMOTHERAPY, 1957, 12 (02) :194-208
[9]  
Corinna M., 2009, Ger., Patent No. 19963179
[10]   Cd(ClO4)2•xH2O as a novel catalyst for the synthesis of α-aminophosphonates under solvent-free conditions [J].
Dindulkar, Someshwar D. ;
Reddy, Mudumala Veeranarayana ;
Jeong, Yeon Tae .
CATALYSIS COMMUNICATIONS, 2012, 17 :114-117