ONE-POT SYNTHESIS OF NOVEL RHODANINE BASED KETENIMINES VIA MULTICOMPONENT REACTIONS

被引：7
作者：
Baharfar, Robabeh [1 ]
Porahmad, Nasim [1 ]
机构：
[1] Univ Mazandaran, Dept Chem, Babol Sar, Iran
来源：
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2011年 / 186卷 / 09期
关键词：
Alkyl isocyanides; dialkyl acetylenedicarboxylates; 5-(4-dimethylaminobenzylidene)-rhodanine; ketenimines; rhodanine; three-component reaction; TERT-BUTYL ISOCYANIDE; DIALKYL ACETYLENEDICARBOXYLATES; ACETYLENIC ESTERS; INHIBITORS; CONSTRUCTION; DERIVATIVES;
D O I：
10.1080/10426507.2011.557418
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Synthesis of polyfunctionalized ketenimines via three-component reactions of rhodanine and 5-(4-dimethylaminobenzylidene)-rhodanine with dialkyl acetylenedicarboxylates and alkyl isocyanides is described. The reactions proceed smoothly under mild conditions leading to the desired products in good yields. In the case of methyl acetylenecarboxylate, the reaction led to methyl (Z)-3-({5-[(E)-1-(tert-butylamino)methylidene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl}sulfanyl)-2-propenoate in low yield.
引用
收藏
页码：1988 / 1996
页数：9
相关论文
共 33 条
[1]   Reactions between isocyanides and dialkyl acetylenedicarboxylates in the presence of 1,2-diacylhydrazines. One-pot synthesis of highly functionalized pyrazoles [J].
Adib, M ;
Sayahi, MH ;
Rahbari, S .
TETRAHEDRON LETTERS, 2005, 46 (38) :6545-6547
[2]   Reaction between isocyanides and dialkyl acetylenedicarboxylates in the presence of 2,4-dihydro-3H-pyrazol-3-ones.: One-pot syntesis of highly functionalized 7-oxo-1H,7H-pyrazolo[1,2-α]pyrazoles [J].
Adib, M ;
Sayahi, MH ;
Aghaaliakbari, B ;
Bijanzadeh, HR .
TETRAHEDRON, 2005, 61 (16) :3963-3966
[3]   Synthesis and biological evaluation of rhodanine derivatives as PRL-3 inhibitors [J].
Ahn, JH ;
Kim, SJ ;
Park, WS ;
Cho, SY ;
Ha, JD ;
Kim, SS ;
Kang, SK ;
Jeong, DG ;
Jung, SK ;
Lee, SH ;
Kim, HM ;
Park, SK ;
Lee, KH ;
Lee, CW ;
Ryu, SE ;
Choi, JK .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (11) :2996-2999
[4]   Reaction between tert-butyl isocyanide, dialkyl acetylenedicarboxylates, and aromatic carboxylic acids:: an efficient method for the synthesis of dialkyl (E)-2{[benzoyl(tert-butyl)amino]carbonyl}-2-butenedioate derivatives [J].
Alizadeh, Abdolah ;
Rostamnia, Sadegh ;
Zhu, Long-Guan .
TETRAHEDRON, 2006, 62 (24) :5641-5644
[5]   Synthesis and cardiotonic activity of imidazo[2,1-b]thiazoles bearing a lactam ring [J].
Andreani, A ;
Rambaldi, M ;
Leoni, A ;
Locatelli, A ;
Bossa, R ;
Chiericozzi, M ;
Galatulas, I ;
Salvatore, G .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1996, 31 (05) :383-387
[6]   SYNTHESIS OF LACTAMS WITH POTENTIAL CARDIOTONIC ACTIVITY [J].
ANDREANI, A ;
RAMBALDI, M ;
LOCATELLI, A ;
LEONI, A ;
BOSSA, R ;
CHIERICOZZI, M ;
GALATULAS, I ;
SALVATORE, G .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (10) :825-829
[7]   Reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates in the presence of 2-acetylbutyrolactone.: Synthesis of functionalized α-methylene-γ-butyrolactones [J].
Asghari, Sakineh ;
Mohammadi, Leila .
TETRAHEDRON LETTERS, 2006, 47 (25) :4297-4299
[8]  
Baharfar R, 2003, J CHEM RES, P616
[9]   A novel approach to the synthesis of highly functionalized thiophenes using isocyanides catalyzed reaction of acetylenic esters with 3-mercapto-2-butanone [J].
Baharfar, Robabeh ;
nia, Roghayeh Hossein ;
Baghbanian, Seyed Meysam .
LETTERS IN ORGANIC CHEMISTRY, 2008, 5 (02) :128-132
[10]   An efficient chemoselective synthesis of O-vinylaryl systems using acetylenic esters and dihydroxybenzenes in the presence of triphenylphosphine or alkyl isocyanides [J].
Baharfar, Robabeh ;
Taghizadeh, Mohammad Javad ;
Ahmadian, Majid ;
Baghbanian, Seyed Meysam .
CHINESE CHEMICAL LETTERS, 2010, 21 (02) :175-178
1234