Recent advances in dearomatization of heteroaromatic compounds

被引:306
作者
Ding, Qiuping [1 ,2 ]
Zhou, Xiaoli [1 ,2 ]
Fan, Renhua [3 ]
机构
[1] Jiangxi Normal Univ, Minist Educ, Key Lab Small Funct Organ Mol, Nanchang 330022, Jiangxi, Peoples R China
[2] Jiangxi Normal Univ, Jiangxis Key Lab Green Chem, Nanchang 330022, Jiangxi, Peoples R China
[3] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
基金
中国国家自然科学基金;
关键词
ENANTIOSELECTIVE ADDITION; TERMINAL ALKYNES; N-ALLOC; INDOLES; ALLYLATION; PYRROLOINDOLINES; CONSTRUCTION; ARYLATION; CYCLIZATION; ALKYLATION;
D O I
10.1039/c4ob00371c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dearomatization reactions provide the most efficient method for the synthesis of spiro- or fused-ring systems from readily available compounds. This review summarizes the recent developments in dearomatization reactions of indoles, pyridines, quinolines, isoquinolines, and some other heteroaromatic compounds. The applications of these methods in total synthesis of natural products are also briefly introduced.
引用
收藏
页码:4807 / 4815
页数:9
相关论文
共 53 条
[1]   Catalytic Asymmetric Additions of Carbon-Centered Nucleophiles to Nitrogen-Containing Aromatic Heterocycles [J].
Ahamed, Muneer ;
Todd, Matthew. H. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (31) :5935-5942
[2]   Electrophile-induced dearomatizing spirocyclization of N-arylisonicotinamides:: A route to spirocyclic piperidines [J].
Arnott, Gareth ;
Brice, Heloise ;
Clayden, Jonathan ;
Blaney, Emma .
ORGANIC LETTERS, 2008, 10 (14) :3089-3092
[3]   Magnesium-Catalyzed Hydroboration of Pyridines [J].
Arrowsmith, Merle ;
Hill, Michael S. ;
Hadlington, Terrance ;
Kociok-Koehn, Gabriele ;
Weetman, Catherine .
ORGANOMETALLICS, 2011, 30 (21) :5556-5559
[4]   Additions to functionalized arenes with concurrent dearomatization [J].
Bach, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (07) :729-730
[5]   Organocatalytic Stereoselective α-Alkylation of Aldehydes with Stable Carbocations [J].
Benfatti, Fides ;
Benedetto, Elena ;
Cozzi, Pier Giorgio .
CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (09) :2047-2052
[6]   Copper-catalyzed coupling of pyridines and quinolines with alkynes: A one-step, asymmetric route to functionalized heterocycles [J].
Black, Daniel A. ;
Beveridge, Ramsay E. ;
Arndtsen, Bruce A. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (05) :1906-1910
[7]   Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones [J].
Brice, Heloise ;
Clayden, Jonathan ;
Hamilton, Stuart D. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2010, 6
[8]   Enantioselective Gold-Catalyzed Synthesis of Polycyclic Indolines [J].
Cera, Gianpiero ;
Chiarucci, Michel ;
Mazzanti, Andrea ;
Mancinelli, Michele ;
Bandini, Marco .
ORGANIC LETTERS, 2012, 14 (05) :1350-1353
[9]   Palladium Catalyzed Decarboxylative Rearrangement of N-Alloc Indoles [J].
Chen, Jun ;
Cook, Matthew J. .
ORGANIC LETTERS, 2013, 15 (05) :1088-1091
[10]  
Ding Q., 2013, SYNTHESIS-STUTTGART, P1