13759-56-3Relevant academic research and scientific papers
Zn(II)-Catalyzed One-Pot Synthesis of Coumarins from Ynamides and Salicylaldehydes
Yoo, Huen Ji,Youn, So Won
, p. 3422 - 3426 (2019/05/10)
A highly efficient and straightforward synthesis of diversely substituted coumarins from ynamides and salicylaldehydes in the presence of Zn(II) catalyst has been developed. The sulfonamide moiety of ynamides was successfully recycled in this process, serving as an effective traceless directing group for high regioselectivity in the bond-forming event. The advantages of this protocol are good functional group tolerance, broad substrate scope, simple and high-yielding reaction, recovery/reuse of the sulfonamides, low catalyst loading of inexpensive catalyst, and, by these merits, a more cost-effective and greener process.
Pd-catalysed carbonylative annulation of salicylaldehydes with benzyl chlorides using N-formylsaccharin as a CO surrogate
Yadav, Vinod K.,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
supporting information, p. 16281 - 16286 (2018/10/04)
A convenient and highly efficient Pd-catalysed carbonylative annulation of salicylaldehydes with benzyl chlorides to afford the corresponding 3-arylcoumarins in good to excellent yields has been developed. Importantly, the protocol utilizes a commercially available, low cost, solid and easy to handle N-formylsaccharin as an alternative to the highly toxic CO gas.
Rh(III)-Catalyzed C-H Activation/Cyclization of Benzamides and Diazonaphthalen-2(1H)-ones for Synthesis of Lactones
Chen, Renjie,Cui, Sunliang
supporting information, p. 4002 - 4005 (2017/08/14)
A Rh(III)-catalyzed C-H activation/cyclization of benzamides and diazonaphthalen-2(1H)-ones for synthesis of lactones has been developed. In the presence of Rh(III) catalysis, the benzamides would form rhodacycle species and could be trapped by diazonaphthalen-2(1H)-ones for arylation, and the following intramolecular lactonization would rapidly furnish the products. Thus, the diazonaphthalen-2(1H)-ones were first revealed as a lactonization component in Rh(III)-catalysis, while the kinetic isotope effect study was conducted and a plausible reaction mechanism was proposed.
A transition-metal-free fast track to flavones and 3-arylcoumarins
Golshani, Mostafa,Khoobi, Mehdi,Jalalimanesh, Nafiseh,Jafarpour, Farnaz,Ariafard, Alireza
supporting information, p. 10676 - 10679 (2017/10/06)
A highly regioselective and transition-metal free one-pot arylation of chromenones with arylboronic acids has been achieved employing K2S2O8. The procedure consists of a sequence of some reactions including an arylation/decarboxylation cascade and proceeds well in aqueous media to afford biologically interesting flavones and 3-arylcoumarins. This method exhibited excellent selectivity and functional group tolerance under mild conditions. The reaction also showed perfect efficacy for the preparation of styryl coumarins.
Base-promoted synthesis of coumarins from salicylaldehydes and aryl-substituted 1,1-dibromo-1-alkenes under transition-metal-free conditions
Liu, Jianming,Zhang, Xin,Shi, Lijun,Liu, Muwen,Yue, Yuanyuan,Li, Fuwei,Zhuo, Kelei
supporting information, p. 9887 - 9890 (2014/08/18)
Facile synthesis of coumarin via the tandem reaction of salicylaldehyde with aryl-substituted 1,1-dibromo-1-alkene was developed. This new protocol proceeds smoothly under mild and transition-metal-free conditions, it allows rapid access to coumarins containing various heteroatoms that are more difficult to prepare by traditional methods. Based on the isolated intermediate of 4-(diethylamino)-3-phenylchroman-2-one and detailed mechanistic studies, a credible tandem pathway was proposed.
A complete switch of the directional selectivity in the annulation of 2-hydroxybenzaldehydes with alkynes
Zeng, Huiying,Li, Chao-Jun
supporting information, p. 13862 - 13865 (2015/01/09)
Controlling reaction selectivity is an eternal pursuit for chemists working in chemical synthesis. As part of this endeavor, our group has been exploring the possibility of constructing different natural product skeletons from the same simple starting mat
Synthesis of 3-arylcoumarins through N-heterocyclic carbene catalyzed condensation and annulation of 2-chloro-2-arylacetaldehydes with salicylaldehydes
Jiang, Yuansong,Chen, Wanzhi,Lu, Weimin
, p. 3669 - 3676 (2013/05/08)
The condensation reaction of 2-chloro-2-arylacetaldehyde with salicylaldehyde catalyzed by N-heterocyclic carbene (NHC) leading to 3-arylcoumarin was studied. A number of 3-arylcoumarin derivatives were obtained in good to excellent yields via this umpolung reaction. This reaction is facile and experimentally simple and mild.
Deracemization of α-aryl hydrocoumarins via catalytic asymmetric protonation of ketene dithioacetals
Lee, Ji-Woong,List, Benjamin
supporting information, p. 18245 - 18248 (2013/01/15)
An unprecedented catalytic asymmetric protonation of ketene dithioacetals is described. Various racemic α-aryl hydrocoumarin derivatives are transformed into enantioenriched dithioacetal-protected hydrocoumarins in the presence of a chiral Br?nsted acid catalyst. A newly developed phosphoric acid, featuring the 3,5-bis(pentafluorothio)phenyl (3,5-(SF5) 2C6H3) substituent, is introduced. The obtained products can be easily converted into either hydrocoumarins or the corresponding chromans via simple hydrolysis or hydrogenation, respectively.
A convenient one-pot synthesis of 4-methyl-3-phenyl-, 3-aryl- and 3-aryl-4-phenylcoumarins
Kamat, Shrivallabh P.,D'Souza, Asha M.,Paknikar, Shashikumar K.,Beauchamp, Philip S.
, p. 242 - 246 (2007/10/03)
Thermal condensation of 2′-hydroxyacetophenones 1a-e with phenylacetic acid 2a in refluxing diphenyl ether gives 4-methyl-3-phenylcoumarins 3a-e. Similarly, reaction of 2-hydroxybenzaldehydes 1f-m and 2-hydroxybenzo-phenones 1n-p with phenylacetic acids 2a-d gives the corresponding 3-arylcoumarins 3f-m and 3-aryl-4-phenylcoumarins 3n-p respectively. Formation of esters 4 and 5 and benzofuran 6 is also observed.
A ONE STEP GENERAL SYNTHESIS OF 3-SUBSTITUTED COUMARINS
Phadke, Chetan P.,Kelkar, Shriniwas L.,Wadia, Murzban S.
, p. 407 - 412 (2007/10/02)
A one step, general synthesis of 3-phenyl and 3-alkyl coumarins, using substituted acetamides and o-hydroxy benzaldehydes is reported.
