Reaction between enaminones and acetylenic esters in the presence of triphenylphosphine: a convenient synthesis of alkyl 2(1-benzyl-2,4-dioxo-2,3,4,5,6,7-hexahydro-1H-indol-3-yl)acetates

被引:12
作者
Nasiri, Farough [1 ]
Bayzidi, Massood [2 ]
Zolali, Amin [2 ]
机构
[1] Univ Mohaghegh Ardabili, Dept Appl Chem, Fac Sci, Ardebil, Iran
[2] Univ Kurdistan, Dept Chem, Fac Sci, Sanandaj, Iran
关键词
beta-Enaminones; Dialkyl acetylenedicarboxylates; Triphenylphosphine; One-pot reaction; ONE-POT SYNTHESIS; DIALKYL ACETYLENEDICARBOXYLATES; FACILE SYNTHESIS; DIMETHYL ACETYLENEDICARBOXYLATE; STEREOSELECTIVE REACTION; MULTICOMPONENT REACTIONS; ACTIVATED ACETYLENES; ISOCYANIDES; DERIVATIVES; DIBENZOYLACETYLENE;
D O I
10.1007/s11030-012-9389-7
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
One-pot reaction between enaminocarbonyl compounds derived from six-membered 1,3-diketones and substituted benzylamines, and electron-deficient acetylenic esters in the presence of triphenylphosphine lead to alkyl 2-(1-benzyl-6,6-dimethyl-2,4-dioxo-2,3,4,5,6,7-hexahydro-1H-indol-3-yl)acetate derivatives in good yields.
引用
收藏
页码:619 / 623
页数:5
相关论文
共 40 条
[21]   Stereoselective reaction between alkyl propiolates and phenols in the presence of sodium azide in tert-butyl alcohol [J].
Nasiri, Farough ;
Malakutikhah, Davood .
MONATSHEFTE FUR CHEMIE, 2011, 142 (08) :807-812
[22]   Two intermediates in the reaction between dibenzoylacetylene and enol systems in the presence of triphenylphosphine in THF/H2O [J].
Nasiri, Farough ;
Bidar, Morteza ;
Atashkar, Bahareh .
MONATSHEFTE FUR CHEMIE, 2009, 140 (04) :463-466
[23]   Synthesis and reactions of stabilized phosphorus ylides [J].
Ramazani, Ali ;
Kazemizadeh, Ali Reza ;
Ahmadi, Ebrahim ;
Noshiranzadeh, Nader ;
Souldozi, Ali .
CURRENT ORGANIC CHEMISTRY, 2008, 12 (01) :59-82
[24]   Enaminones as Building Blocks for the Synthesis of Substituted Pyrazoles with Antitumor and Antimicrobial Activities [J].
Riyadh, Sayed M. .
MOLECULES, 2011, 16 (02) :1834-1853
[25]   Cycloaddition reactions of cross-conjugated enaminones [J].
Singh, Parvesh ;
Sharma, Parul ;
Bisetty, Krishna ;
Mahajan, Mohinder P. .
TETRAHEDRON, 2009, 65 (41) :8478-8485
[26]   Novel oxindole derivatives and their biological activity [J].
Strigácová, J ;
Hudecová, D ;
Mikulásová, M ;
Varecka, L ;
Lásiková, A ;
Végh, D .
FOLIA MICROBIOLOGICA, 2001, 46 (03) :187-192
[27]   Facile synthesis of oxaspirobicyclic butenolides via a domino Michael addition/aldol reaction/γ-lactonization sequence [J].
Teimouri, Mohammad Bagher ;
Abbasi, Tayyebeh .
TETRAHEDRON, 2010, 66 (21) :3795-3800
[28]   Nucleophilic alpha-addition to alkynoates. A synthesis of dehydroamino acids [J].
Trost, BM ;
Dake, GR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (32) :7595-7596
[29]   NOVEL UMPOLUNG IN C-C BOND FORMATION CATALYZED BY TRIPHENYLPHOSPHINE [J].
TROST, BM ;
LI, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3167-3168
[30]   A one-pot entry to a novel 3-H-benzo[d]pyrazolo[1,5-b]isothiazole ring system [J].
Vicini, Paola ;
Incerti, Matteo ;
Ferretti, Rocco ;
Zanardi, Franca .
MOLECULAR DIVERSITY, 2006, 10 (02) :251-253