Recent Advances on the Synthesis of Heterocycles from Diazo Compounds

被引:0
作者
da Silva, Fernando de C. [1 ]
Jordao, Alessandro K. [1 ]
da Rocha, David R. [1 ]
Ferreira, Sabrina B. [2 ]
Cunha, Anna C. [1 ]
Ferreira, Vitor F. [1 ]
机构
[1] Univ Fed Fluminense, Inst Quim, Dept Quim Organ, BR-24020150 Niteroi, RJ, Brazil
[2] Univ Fed Rio de Janeiro, Inst Quim, Dept Quim Organ, BR-27930560 Rio De Janeiro, Brazil
关键词
Diazo Compounds; metallo carbenoids; carbenes; transition metals; heterocycles; C-H INSERTION; BESTMANN-OHIRA REAGENT; ONE-POT; 1,3-DIPOLAR CYCLOADDITION; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC CYCLOPROPANATION; RHODIUM CARBENOIDS; ORGANIC-SYNTHESIS; ENANTIOSELECTIVE INSERTION; MULTICOMPONENT REACTIONS;
D O I
10.2174/138527212798993068
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Carbenoids are transient species whose reactivity resembles that of free carbenes. They can be generated by several procedures, for instance, by the interaction of diazo compounds with transition metals, such as copper, ruthenium and rhodium complexes. They are able to react with various unreactive substrates, and their use has become very popular among synthetic organic chemists. The carbenoid transfer reactions are a powerful set of synthetic tools that have attracted attention due to their versatility in constructing several types of bonds and, thus, are used to create a complex skeleton framework. Several catalysts have been designed and employed to promote the decomposition of diazo compounds, making these reactions very useful in organic synthesis. This review intends to illustrate the research efforts that occurred in this field during the last four years, covering novel, biologically important compounds and methodologies involving carbenoid and non-carbenoid reactions from diazo compounds.
引用
收藏
页码:224 / 251
页数:28
相关论文
共 183 条
[11]   Synthesis of methylene- and alkylidenecyclopropane derivatives [J].
Brandi, A ;
Goti, A .
CHEMICAL REVIEWS, 1998, 98 (02) :589-635
[12]   Efficient synthetic method for β-enamino esters using ultrasound [J].
Brandt, CA ;
da Silva, ACMP ;
Pancote, CG ;
Brito, CL ;
da Silveira, MAB .
SYNTHESIS-STUTTGART, 2004, (10) :1557-1559
[13]   CYCLOPROPANES FROM REACTIONS OF TRANSITION-METAL CARBENE COMPLEXES WITH OLEFINS [J].
BROOKHART, M ;
STUDABAKER, WB .
CHEMICAL REVIEWS, 1987, 87 (02) :411-432
[14]   Water: Nature's Reaction Enforcer-Comparative Effects for Organic Synthesis "In-Water" and "On-Water" [J].
Butler, Richard N. ;
Coyne, Anthony G. .
CHEMICAL REVIEWS, 2010, 110 (10) :6302-6337
[15]   Synthesis, biological, and theoretical evaluations of new 1,2,3-triazoles against the hemolytic profile of the Lachesis muta snake venom [J].
Campos, Vinicius R. ;
Abreu, Paula A. ;
Castro, Helena C. ;
Rodrigues, Carlos R. ;
Jordao, Alessandro K. ;
Ferreira, Vitor F. ;
de Souza, Maria C. B. V. ;
Santos, Fernanda da C. ;
Moura, Laura A. ;
Domingos, Thaisa S. ;
Carvalho, Carla ;
Sanchez, Eladio F. ;
Fuly, Andre L. ;
Cunha, Anna C. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (21) :7429-7434
[16]   Rhodium (ii) carbene C-H insertion in water and catalyst reuse [J].
Candeias, Nuno R. ;
Gois, Pedro M. P. ;
Afonso, Carlos A. M. .
QUIMICA NOVA, 2007, 30 (07) :1768-1772
[17]   Rh(II)-catalyzed intramolecular C-H insertion of diazo substrates in water: Scope and limitations [J].
Candeias, Nuno R. ;
Gois, Pedro M. P. ;
Afonso, Carlos A. M. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (15) :5489-5497
[18]   Intramolecular 1,3-dipolar cycloaddition as a route to triazolobenzodiazepines and pyrrolobenzodiazepines [J].
Chambers, Christopher S. ;
Patel, Nilesh ;
Hemming, Karl .
TETRAHEDRON LETTERS, 2010, 51 (37) :4859-4861
[19]   Ruthenium Catalyzed Directing Group-Free C2-Selective Carbenoid Functionalization of Indoles by α-Aryldiazoesters [J].
Chan, Wai-Wing ;
Yeung, Shing-Hin ;
Zhou, Zhongyuan ;
Chan, Albert S. C. ;
Yu, Wing-Yiu .
ORGANIC LETTERS, 2010, 12 (03) :604-607
[20]   Organic Synthesis "On Water" [J].
Chanda, Arani ;
Fokin, Valery V. .
CHEMICAL REVIEWS, 2009, 109 (02) :725-748