Three-component access to pyrroles promoted by the CAN-silver nitrate system under high-speed vibration milling conditions: a generalization of the Hantzsch pyrrole synthesis

被引:135
作者
Estevez, Veronica [1 ]
Villacampa, Mercedes [1 ]
Carlos Menendez, J. [1 ]
机构
[1] Univ Complutense, Fac Farm, Dept Quim Organ & Farmaceut, E-28040 Madrid, Spain
关键词
SOLVENT-FREE; MULTICOMPONENT; CATALYST; KETONES;
D O I
10.1039/c2cc38099d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A sequential multicomponent process involving the high-speed vibration milling of ketones with N-iodosuccinimide and p-toluenesulfonic acid, followed by addition of a mixture of primary amines, beta-dicarbonyl compounds, cerium(IV) ammonium nitrate and silver nitrate afforded polysubstituted, functionalized pyrroles. This one-pot, solid-state process can be considered as the coupling of an alpha-iodoketone preparation with a general version of the classical Hantzsch pyrrole synthesis.
引用
收藏
页码:591 / 593
页数:3
相关论文
共 26 条
[1]   Polythiophene- and polypyrrole-based mono- and multilayers [J].
Berlin, Anna ;
Vercelli, Barbara ;
Zotti, Gianni .
POLYMER REVIEWS, 2008, 48 (03) :493-530
[2]  
Coquerel Y., 2010, ADV SYNTHETIC CHEM, V1
[3]   Recent developments in asymmetric multicomponent reactions [J].
de Graaff, Corien ;
Ruijter, Eelco ;
Orru, Romano V. A. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (10) :3969-4009
[4]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[5]   Diversity Oriented Syntheses of Conventional Heterocycles by Smart Multi Component Reactions (MCRs) of the Last Decade [J].
Eckert, Heiner .
MOLECULES, 2012, 17 (01) :1074-1102
[6]  
Elders N, 2010, TOP HETEROCYCL CHEM, V23, P129, DOI 10.1007/7081_2009_24
[7]   Multicomponent reactions for the synthesis of pyrroles [J].
Estevez, Veronica ;
Villacampa, Mercedes ;
Carlos Menendez, J. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (11) :4402-4421
[8]   Chemistry and biology of roseophilin and the prodigiosin alkaloids:: A survey of the last 2500 years [J].
Fürstner, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3582-3603
[9]  
Hantzsch A., 1890, BER DTSCH CHEM GES, V23, P1474, DOI [DOI 10.1002/CBER.189002301243, 10.1002/cber.189002301243]
[10]   One-Step Continuous Flow Synthesis of Highly Substituted Pyrrole-3-carboxylic Acid Derivatives via in Situ Hydrolysis of tert-Butyl Esters [J].
Herath, Ananda ;
Cosford, Nicholas D. P. .
ORGANIC LETTERS, 2010, 12 (22) :5182-5185