Microwave Assisted Organic Synthesis of Heterocycles in Aqueous Media: Recent Advances in Medicinal Chemistry

被引:24
作者
Frecentese, Francesco [1 ]
Saccone, Irene [1 ]
Caliendo, Giuseppe [1 ]
Corvino, Angela [1 ]
Fiorino, Ferdinando [1 ]
Magli, Elisa [1 ]
Perissutti, Elisa [1 ]
Severino, Beatrice [1 ]
Santagada, Vincenzo [1 ]
机构
[1] Univ Naples Federico II, Dipartimento Farm, Via D Montesano 49, I-80131 Naples, Italy
关键词
Dielectric heating; green chemistry; heterocycles; indoles; medicinal chemistry; microwave; nucleosides; purine bases; pyridines; pyrimidines; tetrazoles; triazoles; water; HIGH-THROUGHPUT SYNTHESIS; EFFICIENT SYNTHESIS; DRUG DISCOVERY; INTRAMOLECULAR CYCLIZATION; WATER; DERIVATIVES; IRRADIATION; GREEN; INDOLES; FACILE;
D O I
10.2174/1573406412666160502153553
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Background: Green chemistry is a discipline of great interest in medicinal chemistry. It involves all fields of chemistry and it is based on the principle to conduct chemical reactions protecting the environment at the same time, through the use of chemical procedures able to avoid pollution. In this context, water as solvent is a good choice because it is abundant, nontoxic, non-caustic, and non-combustible. Even if microwave assisted organic reactions in conventional solvents have quickly progressed, in the recent years medicinal chemists have focused their attention to processes deemed not dangerous for the environment, using nanotechnology and greener solvents as water. Objective: Several reports of reaction optimizations and selectivities, demonstrating the capability of microwave to allow the obtaining of increased yields have been recently published using water as solvent. In this review, we selected the available knowledge related to microwave assisted organic synthesis in aqueous medium, furnishing examples of the newest strategies to obtain useful scaffolds and novel derivatives for medicinal chemistry purposes. Conclusion: The intention of this review is to demonstrate the exclusive ability of MAOS in water as solvent or as co-solvent. For this purpose we report here the most representative applications of MAOS using water as solvent, focusing on medicinal chemistry processes leading to interesting nitrogen containing heterocycles with potential pharmaceutical applications.
引用
收藏
页码:720 / 732
页数:13
相关论文
共 103 条
[1]   Recent applications of microwave irradiation to medicinal chemistry [J].
Alcazar, Jesus ;
Oehlrich, Daniel .
FUTURE MEDICINAL CHEMISTRY, 2010, 2 (02) :169-176
[2]   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
[3]  
AYSOLA P, 1988, ANAL LETT, V21, P2003
[4]   Microwave reactions under continuous flow conditions [J].
Baxendale, Ian R. ;
Hayward, John J. ;
Ley, Steven V. .
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2007, 10 (10) :802-836
[5]   Synthesis of Some Salicylaldehyde-Based Schiff Bases in Aqueous Media [J].
Bhagat, Sunita ;
Sharma, Nutan ;
Chundawat, Tejpal Singh .
JOURNAL OF CHEMISTRY, 2013, 2013
[6]   Determining the geometries of transition states by use of antihydrophohic additives in water [J].
Breslow, R .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (07) :471-478
[7]   HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].
BRESLOW, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164
[8]  
Brown DJ., 1997, COMPREHENSIVE HETERO, V3, P57
[9]   2-Aryl and 2-heteroaryl pyrrolo[2,3-b]quinoxalines via copper-catalyzed reaction of 1-alkynes with 2-bromo-3-trifluoroacetamidoquinoxaline [J].
Cacchi, S ;
Fabrizi, G ;
Parisi, LM ;
Bernini, R .
SYNLETT, 2004, (02) :287-290
[10]   MICROWAVE-ASSISTED ORGANIC-REACTIONS [J].
CADDICK, S .
TETRAHEDRON, 1995, 51 (38) :10403-10432