Regioselective transition metal-free acylation of coumarins via cross-dehydrogenative coupling reaction of coumarins and aldehydes

被引:16
作者
Adib, Mehdi [1 ]
Rajai-Daryasarei, Saideh [1 ]
Pashazadeh, Rahim [1 ]
Tajik, Mahnaz [1 ]
Mirzaei, Peiman [2 ]
机构
[1] Univ Tehran, Coll Sci, Sch Chem, POB 14155-6455, Tehran, Iran
[2] Shahid Beheshti Univ, Dept Chem, Tehran, Iran
关键词
Cross-dehydrogenative coupling; Transition metal-free; Coumarins; Aldehydes; 3-Acylcoumarins; Acylation; POTENTIAL ANTIVIRAL AGENTS; BOND FORMATION; ACYCLIC DERIVATIVES; N-HETEROCYCLES; INHIBITORS; ALKYNOATES; ETHERS; GLYCOSIDOPYRROLES; POLYFLUOROARENE; ANTIBACTERIAL;
D O I
10.1016/j.tetlet.2016.06.061
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A transition metal-free cross-dehydrogenative coupling reaction is described for the preparation of 3-acylcoumarins. Heating a mixture of a coumarin, an aldehyde, and the K2S2O8/Aliquat 336 system in chlorobenzene at 100 degrees C for 8 h regioselectively afforded the corresponding 3-acylcoumarin derivatives in good to excellent yields. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3701 / 3705
页数:5
相关论文
共 66 条
[1]   A highly diastereoselective five-component synthesis of 1-(alkylimino)-5,5-dicyano-3a-aryloctahydro-3-oxacyclobuta[cd]pentalene-1a,2,5a,5b(2H,3aH)-tetracarboxylates [J].
Adib, Mehdi ;
Sheikhi, Ehsan ;
Haghshenas, Pouyan ;
Rajai-Daryasarei, Saideh ;
Bijanzadeh, Hamid Reza ;
Zhu, Long-Guan .
TETRAHEDRON LETTERS, 2014, 55 (36) :4983-4986
[2]   Regiospecific Benzoylation of Electron-Deficient N-Heterocycles with Methylbenzenes via a Minisci-Type Reaction [J].
Ali, Wajid ;
Behera, Ahalya ;
Guin, Srimanta ;
Patel, Bhisma K. .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (11) :5625-5632
[3]  
Almerico AM, 1997, FARMACO, V52, P667
[4]   Glycosidopyrroles - Part 1. Acyclic derivatives: 1-(2-hydroxyethoxy)methylpyrroles as potential anti-viral agents [J].
Almerico, AM ;
Diana, P ;
Barraja, P ;
Dattolo, G ;
Mingoia, F ;
Loi, AG ;
Scintu, F ;
Milia, C ;
Puddu, I ;
La Colla, P .
FARMACO, 1998, 53 (01) :33-40
[5]   A review on coumarins as acetylcholinesterase inhibitors for Alzheimer's disease [J].
Anand, Preet ;
Singh, Baldev ;
Singh, Nirmal .
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (03) :1175-1180
[6]   No effect of the novel antidiabetic agent nateglinide on the pharmacokinetics and anticoagulant properties of warfarin in healthy volunteers [J].
Anderson, DM ;
Shelley, S ;
Crick, N ;
Buraglio, M .
JOURNAL OF CLINICAL PHARMACOLOGY, 2002, 42 (12) :1358-1365
[7]   Cross-Dehydrogenative Coupling of Azoles with α-C(sp3)-H of Ethers and Thioethers under Metal-Free Conditions: Functionalization of H-N Azoles via C-H Activation [J].
Aruri, Hariprasad ;
Singh, Umed ;
Sharma, Sumit ;
Gudup, Satish ;
Bhogal, Mukesh ;
Kumar, Sanjay ;
Singh, Deepika ;
Gupta, Vivek K. ;
Kant, Rajni ;
Vishwakarma, Ram A. ;
Singh, Parvinder Pal .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03) :1929-1936
[8]   Design, synthesis and anticancer activities of stilbene-coumarin hybrid compounds: Identification of novel proapoptotic agents [J].
Belluti, Federica ;
Fontana, Gabriele ;
Dal Bo, Laura ;
Carenini, Nives ;
Giommarelli, Chiara ;
Zunino, Franco .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (10) :3543-3550
[9]  
Brimble M. A., 2008, COMPREHENSIVE HETERO, V7, P425
[10]   TBHP/TFA mediated oxidative cross-dehydrogenative coupling of N-heterocycles with aldehydes [J].
Chen, Jiayu ;
Wan, Miao ;
Hua, Jing ;
Sun, Yi ;
Lv, Zheng ;
Li, Wei ;
Liu, Lei .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (47) :11561-11566