An efficient synthesis of 4H-chromene, 4H-pyran, and oxepine derivatives via one-pot three-component tandem reactions

被引:51
作者
Kazemi, Bagher [1 ]
Javanshir, Shahrzad [1 ]
Maleki, Ali [1 ]
Safari, Mostafa [1 ]
Khavasi, Hamid Reza [2 ]
机构
[1] Iran Univ Sci & Technol, Dept Chem, Tehran 1684613114, Iran
[2] Shahid Beheshti Univ, Dept Chem, Tehran 1983953113, Iran
关键词
Oxepine; Pyran; Chromene; Multicomponent reaction; Dialkyl acetylenedicarboxylate; Malononitrile; ISOCYANIDES; SCAFFOLD; ETHERS;
D O I
10.1016/j.tetlet.2012.10.046
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new and efficient method has been developed for the synthesis of highly functionalized 2-amino-4H-pyran, 2-amino-4H-chromene, 2-amino-oxepine, and 2-hydroxy-oxepine derivatives through one-pot, three-component tandem reactions of structurally diverse 1,3-diketones, dialkyl acetylenedi-carboxylates, and malononitrile or ethyl cyanoacetate in the presence of a catalytic amount of Na2CO3 in ethanol. This efficient technique has the advantages of giving products in good to high yields, in short reaction times, and with a simple isolation procedure. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6977 / 6981
页数:5
相关论文
共 32 条
[1]   Synthesis of substituted acetylenes, aryl-alkyl ethers, 2-alkene-4-ynoates and nitriles using heterogeneous mesoporous Pd-MCM-48 as reusable catalyst [J].
Banerjee, Subhash ;
Khatri, Hari ;
Balasanthiran, Vagulejan ;
Koodali, Ranjit T. ;
Sereda, Grigoriy .
TETRAHEDRON, 2011, 67 (32) :5717-5724
[2]   Efficient atom economical one-pot multicomponent synthesis of densely functionalized 4H-chromene derivatives [J].
Boominathan, Muthusamy ;
Nagaraj, Muthupandi ;
Muthusubramanian, Shanmugam ;
Krishnakumar, Rajaputi Venkatraman .
TETRAHEDRON, 2011, 67 (33) :6057-6064
[3]   Synthesis and biological studies of flexible brevetoxin/ciguatoxin models with marked conformational preference [J].
Candenas, ML ;
Pinto, FM ;
Cintado, CG ;
Morales, EQ ;
Brouard, I ;
Díaz, MT ;
Rico, M ;
Rodríguez, E ;
Rodríguez, RM ;
Pérez, R ;
Pérez, RL ;
Martín, JD .
TETRAHEDRON, 2002, 58 (10) :1921-1942
[4]   Organocatalyzed synthesis of 2-amino-8-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles [J].
Ding, Derong ;
Zhao, Cong-Gui .
TETRAHEDRON LETTERS, 2010, 51 (09) :1322-1325
[5]   Four new bioactive lobane diterpenes of the soft coral Lobophytum pauciflorum from Mindoro, Philippines [J].
Edrada, RA ;
Proksch, P ;
Wray, V ;
Witte, L ;
van Ofwegen, LP .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (03) :358-361
[6]   METHODS FOR DRUG DISCOVERY - DEVELOPMENT OF POTENT, SELECTIVE, ORALLY EFFECTIVE CHOLECYSTOKININ ANTAGONISTS [J].
EVANS, BE ;
RITTLE, KE ;
BOCK, MG ;
DIPARDO, RM ;
FREIDINGER, RM ;
WHITTER, WL ;
LUNDELL, GF ;
VEBER, DF ;
ANDERSON, PS ;
CHANG, RSL ;
LOTTI, VJ ;
CERINO, DJ ;
CHEN, TB ;
KLING, PJ ;
KUNKEL, KA ;
SPRINGER, JP ;
HIRSHFIELD, J .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (12) :2235-2246
[7]   Electrogenerated base-promoted synthesis of tetrahydrobenzo[b]pyran derivatives [J].
Fotouhi, Lida ;
Heravi, Majid M. ;
Fatehi, Azadeh ;
Bakhtiari, Khadijeh .
TETRAHEDRON LETTERS, 2007, 48 (31) :5379-5381
[8]   Synthesis of Oxepines and 2-Branched Pyranosides from a D-Glucal-Derived gem-Dibromo-1,2-cyclopropanated Sugar [J].
Hewitt, Russell J. ;
Harvey, Joanne E. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03) :955-958
[9]  
Javanshir S., 2011, J SAUDI CHEM SOC
[10]   Solvent-free Knoevenagel condensations and Michael additions in the solid state and in the melt with quantitative yield [J].
Kaupp, G ;
Naimi-Jamal, MR ;
Schmeyers, J .
TETRAHEDRON, 2003, 59 (21) :3753-3760