An efficient regioselective synthesis of highly functionalized 3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidines via an isocyanide-based three-component reaction

被引:24
作者
Esmaeili, Abbas Ali [1 ,2 ]
Zangouei, Mandieh [1 ]
Fakhari, Ali Reza [3 ]
Habibi, Azizollah [4 ]
机构
[1] Univ Birjand, Dept Chem, Birjand, Iran
[2] Ferdowsi Univ Mashhad, Dept Chem, Mashhad, Iran
[3] Shahid Beheshti Univ, Fac Sci, Dept Chem, GC, Tehran, Iran
[4] Univ Tarbiatmoallem, Fac Chem, Tehran 1571914911, Iran
关键词
2-Imino-1,3-thiazolidin-4-one; Dialkyl acetylenedicarboxylates; Alkyl isocyanides; Thiazolo[3,2-a]pyrimidine; ASSISTED COMBINATORIAL SYNTHESIS; ONE-POT SYNTHESIS; MULTICOMPONENT REACTIONS; CONVENIENT SYNTHESIS; DERIVATIVES; THIAZOLOPYRIMIDINES; PYRIMIDINE; LIBRARIES; ROUTE; ACID;
D O I
10.1016/j.tetlet.2012.01.005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We present a novel, convenient, and efficient method for synthesizing polysubstituted 3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidines via a three-component reaction. The zwitterions generated from the reaction of isocyanides and dialkyl acetylenedicarboxylates react with 2-imino-1,3-thiazolidin-4-one to produce the title compounds in good yields. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1351 / 1353
页数:3
相关论文
共 50 条
[1]  
Adib M., 2007, SYNLETT, P27031
[2]  
Alam O., 2009, MED CHEM RES, P9267
[3]  
ALLEN CFH, 1947, ORG SYNTH, V27, P71
[4]  
BALKAN A, 1992, PHARMAZIE, V47, P687
[5]   Multicomponent synthesis of benzoxazinones via tandem Ugi/Mitsunobu reactions: an unexpected cine-substitution [J].
Banfi, Luca ;
Basso, Andrea ;
Guanti, Giuseppe ;
Lecinska, Paulina ;
Riva, Renata .
MOLECULAR DIVERSITY, 2008, 12 (3-4) :187-190
[6]   Recent advances in multicomponent reactions for diversity-oriented synthesis [J].
Biggs-Houck, James E. ;
Younai, Ashkaan ;
Shaw, Jared T. .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2010, 14 (03) :371-382
[7]   Tuning of chemo- and regioselectivities in multicomponent condensations of 5-aminopyrazoles, dimedone, and aldehydes [J].
Chebanov, Valentin A. ;
Saraev, Vyacheslav E. ;
Desenko, Sergey M. ;
Chernenko, Vitaliy N. ;
Knyazeva, Irina V. ;
Groth, Ulrich ;
Glasnov, Tortia N. ;
Kappe, C. Oliver .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (13) :5110-5118
[8]   MESOIONIC PURINONE ANALOGS .4. SYNTHESIS AND IN-VITRO ANTIBACTERIAL PROPERTIES OF MESOIONIC "THIAZOLO[3,2-A]PYRIMIDIN-5,7-DIONES AND MESOIONIC 1,3,4-THIADIAZOLO[3,2-A]PYRIMIDIN-5,7-DIONES [J].
COBURN, RA ;
GLENNON, RA .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1973, 62 (11) :1785-1789
[9]   A facile route to 2,4-dihydro-1H-benzo[d][1,3]thiazines via silver-catalyzed tandem addition-cyclization reactions [J].
Ding, Qiuping ;
Wu, Jie .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (04) :541-545
[10]   Comprehensive Survey of Chemical Libraries for Drug Discovery and Chemical Biology: 2007 [J].
Dolle, Roland E. ;
Le Bourdonnec, Bertrand ;
Goodman, Allan J. ;
Morales, Guillermo A. ;
Thomas, Craig J. ;
Zhang, Wei .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (06) :753-802