Microwave-assisted novel synthesis of amino-thieno[3,2-b]pyridines under solvent-free conditions

被引:12
作者
Su, Weike [1 ]
Guo, Shaozheng [1 ]
Hong, Zhi [1 ,2 ]
Chen, Ren'er [2 ]
机构
[1] Zhejiang Univ Technol, Key Lab Pharmaceut Engn, Minist Educ, Coll Pharmaceut Sci, Hangzhou 310014, Zhejiang, Peoples R China
[2] Taizhou Univ, Sch Pharmaceut & Chem Engn, Linhai 317000, Peoples R China
基金
浙江省自然科学基金; 中国国家自然科学基金;
关键词
Microwave-assisted; Solvent-free; Ytterbium triflate; Amino-thieno[2,3-b]pyridine derivatives; Combes reaction; TYROSINE KINASE INHIBITORS; GROWTH-FACTOR RECEPTOR; ATP-BINDING-SITE; YTTERBIUM(III) TRIFLATE; ORGANIC-SYNTHESIS; DERIVATIVES; IRRADIATION; PYRIMIDINE; ALCOHOLS; SERIES;
D O I
10.1016/j.tetlet.2010.08.075
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the presence of a catalytic amount of ytterbium(III) triflate and under microwave irradiation, mixtures of 2-amino-3-thiophenecarbonitriles, ketones, and silica gel afforded smoothly the corresponding aminothieno[2,3-b]pyridine derivatives in one step. A wide variety of ketones were tested under these conditions. The reactions proceeded rapidly and afforded the desired products in good to excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5718 / 5720
页数:3
相关论文
共 35 条
[1]   Fast microwave-assisted preparation of aryl and vinyl nitriles and the corresponding tetrazoles from organo-halides [J].
Alterman, M ;
Hallberg, A .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :7984-7989
[2]   Recent developments in microwave-assisted, transition-metal-catalysed C-C and C-N bond-forming reactions [J].
Appukkuttan, Prasad ;
Van der Eycken, Erik .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (07) :1133-1155
[3]  
Bagley MC, 2001, SYNLETT, P1523
[4]  
Bergstrom F.W., 1944, Chem. Rev, V3 5, P156
[5]   MECHANISM OF FORMATION OF BENZO[G]QUINOLONES VIA COMBES REACTION [J].
BORN, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (24) :3952-&
[6]   DESIGN AND SYNTHESES OF 4-ACYLAMINOPYRIDINE DERIVATIVES - NOVEL HIGH-AFFINITY CHOLINE UPTAKE ENHANCERS .2. [J].
CHAKI, H ;
YAMABE, H ;
SUGANO, M ;
MORITA, S ;
BESSHO, T ;
TABATA, R ;
SAITO, KI ;
EGAWA, M ;
TOBE, A ;
MORINAKA, Y .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (14) :1495-1500
[7]  
Combes A., 1888, B CHIM SOC FRANCE, V49, P89
[8]   Carbamate synthesis from amines and dimethyl carbonate under ytterbium triflate catalysis [J].
Curini, M ;
Epifano, F ;
Maltese, F ;
Rosati, O .
TETRAHEDRON LETTERS, 2002, 43 (28) :4895-4897
[9]   Ytterbium triflate promoted synthesis of 1,5-benzodiazepine derivatives [J].
Curini, M ;
Epifano, F ;
Marcotullio, MC ;
Rosati, O .
TETRAHEDRON LETTERS, 2001, 42 (18) :3193-3195
[10]  
de la Hoz A, 2000, EUR J ORG CHEM, V2000, P3659