Multicomponent Reactions of Aldo-X Bifunctional Reagent -Oxoketene Dithioacetals and Indoles or Amines: Divergent Synthesis of Dihydrocoumarins, Quinolines, Furans, and Pyrroles

被引:52
作者
Liu, Changhui [1 ]
Zhou, Li [1 ]
Jiang, Dan [1 ]
Gu, Yanlong [1 ,2 ]
机构
[1] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, Key Lab Mat Chem Energy Convers & Storage, Minist Educ, 1037 Luoyu Rd, Wuhan 430074, Peoples R China
[2] Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
alpha-oxoketene dithioacetals; amines; aldo-X reagents; indoles; multicomponent reactions; DENSELY FUNCTIONALIZED 4H-CHROMENES; 2 DIFFERENT NUCLEOPHILES; ONE-POT SYNTHESIS; AROYLKETENE DITHIOACETALS; 3-COMPONENT REACTIONS; MEDICINAL CHEMISTRY; ANTICANCER AGENTS; HETEROCYCLES; EFFICIENT; DERIVATIVES;
D O I
10.1002/ajoc.201500497
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Six multicomponent reactions were developed by using aldo-X reagents and -oxoketene dithioacetals with indoles or amines as substrates, which can be used to prepare many heterocycles, such as dihydrocoumarins, quinolines, furans and pyrroles, in a straightforward way. A combination of two bifunctional aldo-X reagents and -oxoketene dithioacetals is the key to make the discovery of these multicomponent reactions possible because these reagents have a minimum of two reactive sites, which enable different substrates to be assembled together in various manners.
引用
收藏
页码:367 / 372
页数:6
相关论文
共 69 条
[1]   Silver and gold-catalyzed multicomponent reactions [J].
Abbiati, Giorgio ;
Rossi, Elisabetta .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 :481-513
[2]   Synthesis of 3-aroylnicotinonitriles from aroylketene dithioacetals [J].
Anabha, E. R. ;
Nirmala, K. N. ;
Thomas, Abraham ;
Asokan, C. V. .
SYNTHESIS-STUTTGART, 2007, (03) :428-432
[3]   Stereoconvergent synthesis of 1-deoxynojirimycin isomers by using the 3 component 4 centred Ugi reaction [J].
Azad, Chandra S. ;
Saxena, Anil K. .
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (06) :665-669
[4]   Enantioselective One-Pot Synthesis of 2-Amino-4-(indol-3-yl)-4H-Chromenes [J].
Chen, Weiliang ;
Cai, Yunfei ;
Fu, Xuan ;
Liu, Xiaohua ;
Lin, Lili ;
Feng, Xiaoming .
ORGANIC LETTERS, 2011, 13 (18) :4910-4913
[5]   The condensation of salicylaldehydes and malononitrile revisited:: Synthesis of new dimeric chromene derivatives [J].
Costa, Marta ;
Areias, Filipe ;
Abrunhosa, Luis ;
Venancio, Armando ;
Proenca, Fernanda .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (05) :1954-1962
[6]   Recent developments in asymmetric multicomponent reactions [J].
de Graaff, Corien ;
Ruijter, Eelco ;
Orru, Romano V. A. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (10) :3969-4009
[7]   The coupling-isomerization approach to enimines and the first sequential three-component access to 2-ethoxy pyridines [J].
Dediu, OG ;
Yehia, NAM ;
Müller, TJJ .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2004, 59 (04) :443-450
[8]   Enantioselective Catalytic Reactions with N-Acyliden Penta-atomic Aza-heterocycles. Heterocycles as Masked Bricks To Build Chiral Scaffolds [J].
Desimoni, Giovanni ;
Faita, Giuseppe ;
Quadrelli, Paolo .
CHEMICAL REVIEWS, 2015, 115 (18) :9922-9980
[9]  
Dong Y., 2014, Angew. Chem., V126, P3510, DOI 10.1002/ange.201310340
[10]   Palladium-Catalyzed C-S Activation/Aryne Insertion/Coupling Sequence: Synthesis of Functionalized 2-Quinolinones [J].
Dong, Ying ;
Liu, Bangyu ;
Chen, Peng ;
Liu, Qun ;
Wang, Mang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (13) :3442-3446