Synthesis of β-carbolines using microwave-assisted aza-Wittig methodology in ionic liquids

被引:8
作者
Fresneda, Pilar M. [1 ]
Antonio Blazquez, Jose [1 ]
机构
[1] Univ Murcia, Fac Quim, Dept Quim Organ, E-30100 Murcia, Spain
关键词
beta-Carbolines; Iminophosphoranes; Aza-Wittig reaction; Microwave irradiation; Ionic liquids; PALLADIUM-CATALYZED IMINOANNULATION; ORGANIC-SYNTHESIS; GAMMA-CARBOLINES; MARINE ORIGIN; ANTITUMOR AGENTS; DERIVATIVES; ALKALOIDS; HETEROCYCLES; RING; BIOACTIVITY;
D O I
10.1016/j.tetlet.2012.03.049
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The improved preparation of 1-substituted-beta-carbolines is reported using microwave-assisted aza-Wittig/electrocyclic ring-closure reaction with ionic liquids as solvent. In all cases an unprecedented N-methoxymethyl group (MOM) deprotection is observed. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2618 / 2621
页数:4
相关论文
共 71 条
[1]   Trialkyl-Substituted Imidazolium-Based Ionic Liquids for Electrochemical Applications: Basic Physicochemical Properties [J].
Andriyko, Yuriy O. ;
Reischl, Wolfgang ;
Nauer, Gerhard E. .
JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2009, 54 (03) :855-860
[2]  
[Anonymous], 2008, IONIC LIQUIDS SYNTHE
[3]   Recent developments in microwave-assisted, transition-metal-catalysed C-C and C-N bond-forming reactions [J].
Appukkuttan, Prasad ;
Van der Eycken, Erik .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (07) :1133-1155
[4]  
Attenni B., 2005, GB Patent, Patent No. [WO2005/02319A1, 200502319]
[5]   Preparation of Fused Tetracyclic Quinazolinones by Combinations of Aza-Wittig Methodologies and CuI-Catalysed Heteroarylation Processes [J].
Bleda, Juan Antonio ;
Fresneda, Pilar M. ;
Orenes, Raul ;
Molina, Pedro .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (15) :2490-2504
[6]   Solid-phase synthesis of tetrahydro-β-carbolinehydantoins via the N-acyliminium Pictet-Spengler reaction and cyclative cleavage [J].
Bonnet, D ;
Ganesan, A .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2002, 4 (06) :546-548
[7]   Synthesis and biological studies of 1-amino β-carbolines [J].
Boursereau, Y ;
Coldham, I .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (23) :5841-5844
[8]   Synthesis and evaluation of β-carboline derivatives as inhibitors of human immunodeficiency virus [J].
Brahmbhatt, Keyur G. ;
Ahmed, Nafees ;
Sabde, Sudeep ;
Mitra, Debashis ;
Singh, Inder Pal ;
Bhutani, Kamlesh K. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (15) :4416-4419
[9]   More Sustainable Approaches for the Synthesis of N-Based Heterocycles [J].
Candeias, Nuno R. ;
Branco, Luis C. ;
Gois, Pedro M. P. ;
Afonso, Carlos A. M. ;
Trindade, Alexandre F. .
CHEMICAL REVIEWS, 2009, 109 (06) :2703-2802
[10]   β-Carboline alkaloids:: Biochemical and pharmacological functions [J].
Cao, Rihui ;
Peng, Wenlie ;
Wang, Zihou ;
Xu, Anlong .
CURRENT MEDICINAL CHEMISTRY, 2007, 14 (04) :479-500