An expedient sequential one-pot four component synthesis of novel steroidal spiro-pyrrolidine heterocycles in ionic liquid

被引:21
作者
Gavaskar, D. [1 ]
Babu, A. R. Suresh [2 ]
Raghunathan, R. [1 ]
Dharani, M. [3 ]
Balasubramanian, S. [3 ]
机构
[1] Univ Madras, Dept Organ Chem, Guindy Campus, Madras, Tamil Nadu, India
[2] Univ Strasbourg, IBMC, Strasbourg, France
[3] Univ Madras, Dept Inorgan Chem, Guindy Campus, Madras, Tamil Nadu, India
关键词
Estrone; Ionic liquid; Azomethine ylide; Cycloaddition; Indenoquinoxaline; Steroidal pyrrolidine; MEDIATED 3+2 CYCLOADDITION; BIOLOGICAL-ACTIVITY; MULTICOMPONENT REACTIONS; AZOMETHINE YLIDES; DERIVATIVES; FACILE; ANTIBACTERIAL; ESTRONE; LIPS; CONSTRUCTION;
D O I
10.1016/j.steroids.2016.02.010
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
A facile one-pot synthesis of novel steroidal dispiro-indenoquinoxaline pyrrolidines via multicomponent-[3+2]-cycloaddition of azomethine ylides in ionic liquid is described. The structure of cycloadduct is confirmed by IR, H-1 NMR, C-13 NMR, high resolution mass spectroscopy and elemental analysis. (C) 2016 Elsevier Inc. All rights reserved.
引用
收藏
页码:1 / 6
页数:6
相关论文
共 85 条
[1]   Synthesis of novel steroidal heterocyclic derivatives as antibacterial agents [J].
Abdelhalim, Mervat M. ;
El-Saidi, Manal M. T. ;
Rabie, Samira T. ;
Elmegeed, Gamal A. .
STEROIDS, 2007, 72 (05) :459-465
[2]   Synthesis and biological evaluation of some nitrogen containing steroidal heterocycles [J].
Abdelhalim, Mervat M. ;
Kamel, Eman M. ;
Rabie, Samira T. ;
Mohamed, Nadia R. .
STEROIDS, 2011, 76 (1-2) :78-84
[3]   Hybrid molecules of estrone:: New compounds with potential antibacterial, antifungal, and antiproliferative activities [J].
Adamec, J. ;
Beckert, R. ;
Weiss, D. ;
Klimesova, V. ;
Waisser, K. ;
Moellmann, U. ;
Kaustova, J. ;
Buchta, V. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (08) :2898-2906
[4]  
Al-Footy KO, 2010, ORIENT J CHEM, V26, P5
[5]  
Almansour A.I., 2015, MOLECULES, V20, P1
[6]   Oxindoles from Phalaris coerulescens [J].
Anderton, N ;
Cockrum, PA ;
Colegate, SM ;
Edgar, JA ;
Flower, K ;
Vit, I ;
Willing, RI .
PHYTOCHEMISTRY, 1998, 48 (03) :437-439
[7]   Synthesis of novel β-lactam fused spiroisoxazolidine chromanones and tetralones as potent antimicrobial agent for human and plant pathogens [J].
Arumugam, Natarajan ;
Raghunathan, Raghavachary ;
Shanmugaiah, Vellaisamy ;
Mathivanan, Narayanasamy .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (12) :3698-3702
[8]  
Babu A. R. S., 2009, CURR CHEM BIOL, V3, P432
[9]  
Babu A. R. S., 2008, Curr. Chem. Biol, V2, P312, DOI DOI 10.2174/187231308785739729
[10]   An easy access to novel steroidal dispiropyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides [J].
Babu, A. R. Suresh ;
Raghunathan, R. .
TETRAHEDRON LETTERS, 2008, 49 (31) :4618-4620