Recent advances in the synthesis of pyrroles by multicomponent reactions

被引:672
作者
Estevez, Veronica [1 ]
Villacampa, Mercedes [1 ]
Menendez, J. Carlos [1 ]
机构
[1] Univ Complutense, Fac Farm, Dept Quim Organ & Farmaceut, E-28040 Madrid, Spain
关键词
ONE-POT SYNTHESIS; HIGHLY SUBSTITUTED PYRROLES; PROMOTED 3-COMPONENT REACTION; POLYSUBSTITUTED PYRROLES; 1,3-DICARBONYL COMPOUNDS; FUNCTIONALIZED PYRROLES; PROPARGYLIC ALCOHOLS; CONVENIENT SYNTHESIS; PRIMARY AMINES; EFFICIENT;
D O I
10.1039/c3cs60015g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Pyrrole is one of the most important one-ring heterocycles. The ready availability of suitably substituted and functionalized pyrrole derivatives is essential for the progress of many branches of science, including biology and materials science. Access to this key heterocycle by multicomponent routes is particularly attractive in terms of synthetic efficiency, and also from the environmental point of view. We update here our previous review on this topic by describing the progress made in this area in the period between mid-2009 and the end of 2013.
引用
收藏
页码:4633 / 4657
页数:25
相关论文
共 114 条
[101]   Recent Advances in Asymmetric Isocyanide-Based Multicomponent Reactions [J].
van Berkel, Sander S. ;
Bogels, Berry G. M. ;
Wijdeven, Marloes A. ;
Westermann, Bernhard ;
Rutjes, Floris P. J. T. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (19) :3543-3559
[102]   Efficiency, Diversity, and Complexity with Multicomponent Reactions [J].
van der Heijden, Gydo ;
Ruijter, Eelco ;
Orru, Romano V. A. .
SYNLETT, 2013, 24 (06) :666-685
[103]   Design of a Versatile Multicomponent Reaction Leading to 2-amino-5-ketoaryl pyrroles [J].
Wang, Kan ;
Doemling, Alexander .
CHEMICAL BIOLOGY & DRUG DESIGN, 2010, 75 (03) :277-283
[104]   Highly Efficient Chemoselective Synthesis of Polysubstituted Pyrroles via Isocyanide-Based Multicomponent Domino Reaction [J].
Wang, Xiang ;
Xu, Xiao-Ping ;
Wang, Shun-Yi ;
Zhou, Weiqun ;
Ji, Shun-Jun .
ORGANIC LETTERS, 2013, 15 (16) :4246-4249
[105]   Anticancer and immunosuppressive properties of bacterial prodiginines [J].
Williamson, Neil R. ;
Fineran, Peter C. ;
Gristwood, Tamzin ;
Chawrai, Suresh R. ;
Leeper, Finian J. ;
Salmond, George P. C. .
FUTURE MICROBIOLOGY, 2007, 2 (06) :605-618
[106]   Biosynthesis of the red antibiotic, prodigiosin, in Serratia:: identification of a novel 2-methyl-3-n-amyl-pyrrole (MAP) assembly pathway, definition of the terminal condensing enzyme, and implications for undecylprodigiosin biosynthesis in Streptomyces [J].
Williamson, NR ;
Simonsen, HT ;
Ahmed, RAA ;
Goldet, G ;
Slater, H ;
Woodley, L ;
Leeper, FJ ;
Salmond, GPC .
MOLECULAR MICROBIOLOGY, 2005, 56 (04) :971-989
[107]   An efficient and convenient synthesis of 1,2,3-trisubstituted pyrroles via iodocyclization from ethyl acetoacetate [J].
Xu, Pengfei ;
Huang, Kunzhu ;
Liu, Zhiguo ;
Zhou, Ming ;
Zeng, Wenbin .
TETRAHEDRON LETTERS, 2013, 54 (23) :2929-2933
[108]   Efficient and green synthesis of tetrasubstituted pyrroles promoted by task-specific basic ionic liquids as catalyst in aqueous media [J].
Yavari, Issa ;
Kowsari, Elaheh .
MOLECULAR DIVERSITY, 2009, 13 (04) :519-528
[109]   New Pyrrole Alkaloids with Bulky N-Alkyl Side Chains Containing Stereogenic Centers from Lycium chinense [J].
Youn, Ui Joung ;
Kil, Yun-Seo ;
Nam, Joo-Won ;
Lee, Yoo Jin ;
Kim, Jinwoong ;
Lee, Dongho ;
Lee, Je-Hyun ;
Seo, Eun-Kyoung .
HELVETICA CHIMICA ACTA, 2013, 96 (08) :1482-1487
[110]   Direct synthesis of pyrroles via a silver-promoted three-component reaction involving unusual imidazole ring opening [J].
Zeng, Jing ;
Bai, Yaguang ;
Cai, Shuting ;
Ma, Jimei ;
Liu, Xue-Wei .
CHEMICAL COMMUNICATIONS, 2011, 47 (48) :12855-12857