Iodotrimethylsilane-accelerated one-pot synthesis of 5-unsubstituted 3,4-dihydropyrimidin-2(1H)-ones:: A novel procedure for the Biginelli-like cyclocondensation reaction at room temperature

被引:32
作者
Sabitha, G [1 ]
Reddy, KB [1 ]
Srinivas, R [1 ]
Yadav, JS [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India
关键词
D O I
10.1002/hlca.200590242
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel Biginelli-like cyclocondensation reaction is efficiently catalyzed by iodotrimethylsilane (Me(3)Sil) in MeCN. The reaction proceeds at room temperature by a three-component one-pot condensation of ketones with aldehydes and urea to afford 5-unsubstituted 3,4-dihydropyrimidin-2(1H)-ones in good yields (Scheme 1 and Table).
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收藏
页码:2996 / 2999
页数:4
相关论文
共 24 条
[1]   Cyclic ketones and substituted α-keto acids as alternative substrates for novel Biginelli-like scaffold syntheses [J].
Abelman, MM ;
Smith, SC ;
James, DR .
TETRAHEDRON LETTERS, 2003, 44 (24) :4559-4562
[2]   SUBSTITUTED 1,4-DIHYDROPYRIMIDINES .3. SYNTHESIS OF SELECTIVELY FUNCTIONALIZED 2-HETERO-1,4-DIHYDROPYRIMIDINES [J].
ATWAL, KS ;
ROVNYAK, GC ;
OREILLY, BC ;
SCHWARTZ, J .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5898-5907
[3]  
Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[4]   A new substrate for the Biginelli cyclocondensation:: Direct preparation of 5-unsubstituted 3,4-dihydropyrimidin-2(1H)-ones from a β-keto carboxylic acid [J].
Bussolari, JC ;
McDonnell, PA .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) :6777-6779
[5]   Model studies toward the synthesis of dihydropyrimidinyl and pyridyl α-amino acids via three-component biginelli and hantzsch cyclocondensations [J].
Dondoni, A ;
Massi, A ;
Minghini, E ;
Sabbatini, S ;
Bertolasi, V .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6172-6183
[6]   Indium(III) bromide-catalyzed preparation of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction [J].
Fu, NY ;
Yuan, YF ;
Cao, Z ;
Wang, SW ;
Wang, JT ;
Peppe, C .
TETRAHEDRON, 2002, 58 (24) :4801-4807
[7]   Unprecedented catalytic three component one-pot condensation reaction: An efficient synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones [J].
Hu, EH ;
Sidler, DR ;
Dolling, UH .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3454-3457
[8]  
Kappe CO, 1997, TETRAHEDRON, V53, P2803
[9]  
KAPPE CO, 1993, TETRAHEDRON, V49, P6937
[10]   Synthesis and reactions of Biginelli compounds, part 19 - X-ray structure, conformational analysis, enantioseparation, and determination of absolute configuration of the mitotic kinesin Eg5 inhibitor monastrol [J].
Kappe, CO ;
Shishkin, OV ;
Uray, G ;
Verdino, P .
TETRAHEDRON, 2000, 56 (13) :1859-1862