Schwartz reagent mediated synthesis of thiazolones and imidazolones from thiazolidine-2,4-diones and imidazolidine-2,4-diones

被引:6
作者
Dandepally, Srinivasa Reddy [1 ]
Elgoummadi, Radouane [2 ]
Williams, Alfred L. [1 ,2 ]
机构
[1] N Carolina Cent Univ, BRITE, Durham, NC 27707 USA
[2] N Carolina Cent Univ, Dept Pharmaceut Sci, Durham, NC 27707 USA
关键词
Schwartz reagent; Reduction/elimination; Thiazolones; Imidazolones; BIOLOGICAL EVALUATION; REDUCTIVE DEOXYGENATION; TERTIARY AMIDES; HYDROZIRCONATION; INHIBITORS; DERIVATIVES; HYDANTOINS; ZIRCONIUM; ALDEHYDES; RECEPTOR;
D O I
10.1016/j.tetlet.2012.12.015
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel reduction/elimination method of thiazolidine-2,4-dione and imidazolidine-2,4-dione derivatives using Schwartz reagent to synthesize numerous thiazolones and imidazolones in a single step is reported. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:925 / 928
页数:4
相关论文
共 56 条
[1]   Synthesis and anti-inflammatory activity of new arylidene-thiazolidine-2,4-diones as PPARγ ligands [J].
Barros, Cleiton Diniz ;
Amato, Angelica Amorim ;
de Oliveira, Tiago Bento ;
Rocha Iannini, Karime Bicas ;
da Silva, Anekecia Lauro ;
da Silva, Teresinha Goncalves ;
Leite, Elisa Soares ;
Hernandes, Marcelo Zaldini ;
Alves de Lima, Maria do Carmo ;
Galdino, Suely Lins ;
Rocha Neves, Francisco de Assis ;
Pitta, Ivan da Rocha .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (11) :3805-3811
[2]  
Borkar MR, 2009, INDIAN J HETEROCY CH, V18, P295
[3]  
Bozdag-Dündar O, 2006, ARZNEIMITTEL-FORSCH, V56, P621
[4]   VINYLIC ORGANOBORANES .12. SYNTHESIS OF (Z)-1-HALO-1-ALKENES VIA HYDROBORATION OF 1-HALO-1-ALKYNES FOLLOWED BY PROTONOLYSIS [J].
BROWN, HC ;
BLUE, CD ;
NELSON, DJ ;
BHAT, NG .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6064-6067
[5]   1-(3-cyanobenzylpiperidin-4-yl)-5-methyl-4-phenyl-1,3-dihydroimidazol-2-one:: A selective high-affinity antagonist for the human dopamine D4 receptor with excellent selectivity over ion channels [J].
Carling, RW ;
Moore, KW ;
Moyes, CR ;
Jones, EA ;
Bonner, K ;
Emms, F ;
Marwood, R ;
Patel, S ;
Patel, S ;
Fletcher, AE ;
Beer, M ;
Sohal, B ;
Pike, A ;
Leeson, PD .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (14) :2706-2715
[6]  
Cenac N., 1999, J ORG CHEM, V67, P796
[7]   THE STEREOCHEMICAL PROPERTIES OF THE SCHWARTZS REAGENT (ETA-5-C5H5)2ZR(H)CL IN THE REDUCTION OF CYCLIC-KETONES TO ALCOHOLS [J].
CESAROTTI, E ;
CHIESA, A ;
MAFFI, S ;
UGO, R .
INORGANICA CHIMICA ACTA-LETTERS, 1982, 64 (04) :L207-L208
[8]   SELECTIVE REDUCTIONS OF 3-SUBSTITUTED HYDANTOINS TO 4-HYDROXY-2-IMIDAZOLIDINONES AND VICINAL DIAMINES [J].
CORTES, S ;
KOHN, H .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (13) :2246-2254
[9]   Synthesis of imidazoisoindol-3-ones by a palladium-catalyzed intramolecular C-H insertion reaction [J].
Dandepally, Srinivasa Reddy ;
Williams, Alfred L. .
TETRAHEDRON LETTERS, 2009, 50 (13) :1395-1398
[10]   Selective Catalytic Monoreduction of Phthalimides and Imidazolidine-2,4-diones [J].
Das, Shoubhik ;
Addis, Daniele ;
Knoepke, Leif R. ;
Bentrup, Ursula ;
Junge, Kathrin ;
Bruekner, Angelika ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) :9180-9184