Efficient stepwise and one pot three-component synthesis of 2-amino-4-(2-oxo-2H-chromen-3-yl)thiophene-3-carbonitriles

被引:21
作者
Srikrishna, Devulapally [1 ]
Dubey, Pramod Kumar [1 ]
机构
[1] Jawaharlal Nehru Technol Univ Hyderabad, Dept Chem, Coll Engn, Hyderabad 500085, Telangana, India
关键词
3-Acetyl-2H-chromen-2-one; Knoevenagel condensation; Elemental sulfur; Gewald reaction; POLYETHYLENE-GLYCOL PEG-400; FACILE; DERIVATIVES;
D O I
10.1016/j.tetlet.2014.10.021
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Environmentally benign conditions have been developed for the synthesis of 2-amino-4-(2-oxo-2H-chromen-3-yl)thiophene-3-carbonitriles (3) starting from 3-acetyl-2H-chromen-2-one (1) through the intermediacy of 2-(1-(2-oxo-2H-chromen-3-yl)ethylidene)malononitrile (2) using the Knoevenagel condensation followed by the Gewald reaction. Alternatively, 3 could also be prepared in a one pot method by treating equimolar amounts of 1, malononitrile, and elemental sulfur. The merits of this preparation are mild reaction conditions, easy work-up procedure, and good yields. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6561 / 6566
页数:6
相关论文
共 31 条
[1]   Antifungal Activities of New Coumarins [J].
Al-Amiery, Ahmed A. ;
Kadhum, Abdul Amir Hassan ;
Mohamad, Abu Bakar .
MOLECULES, 2012, 17 (05) :5713-5723
[2]  
Bruno D., 2012, HETEROLETTERS, V2, P31
[3]  
Campaigne E., 1990, SULFUR REP, V1, P49
[4]   Synthesis of tetrasubstituted thiophenes on solid-support using the Gewald reaction [J].
Castanedo, GM ;
Sutherlin, DP .
TETRAHEDRON LETTERS, 2001, 42 (41) :7181-7184
[5]   Polyethylene glycol and solutions of polyethylene glycol as green reaction media [J].
Chen, J ;
Spear, SK ;
Huddleston, JG ;
Rogers, RD .
GREEN CHEMISTRY, 2005, 7 (02) :64-82
[6]   Silica gel catalysed Knoevenagel condensation in Dry Media under microwave irradiation [J].
delaCruz, P ;
DiezBarra, E ;
Loupy, A ;
Langa, F .
TETRAHEDRON LETTERS, 1996, 37 (07) :1113-1116
[7]   PEG-600: a facile and eco-friendly reaction medium for the synthesis of N-alkyl derivatives of indole-3-carboxyaldehyde [J].
Dubey, P. K. ;
Venkatanarayana, M. .
GREEN CHEMISTRY LETTERS AND REVIEWS, 2010, 3 (04) :257-261
[8]  
El-Wahab A. H. F. A., 2011, AM J CHEM, V1, P1
[9]  
Gang L, 2010, J MED CHEM, V53, P1741, DOI [10.1021/jm901652p, DOI 10.1021/JM901652P]
[10]   A Convenient Ultrasound-Promoted Synthesis of Some New Thiazole Derivatives Bearing a Coumarin Nucleus and Their Cytotoxic Activity [J].
Gomha, Sobhi M. ;
Khalil, Khaled D. .
MOLECULES, 2012, 17 (08) :9335-9347