19063-55-9Relevant articles and documents
Dicyanovinylcoumarin as a turn-on fluorescent sensor for cyanide ion
Reddy, T. Sheshashena,Choi, Myung-Seok
, p. 108 - 114 (2018)
Dicyanovinylcoumarin chemosensors (4a, 4b and 4c) were designed and synthesized by the Knoevenagel condensation reaction. The electronic absorption and emission spectra of the dicyanovinylcoumarin isomers exhibited red shifted absorption and less emission as compared to their precursor's coumarin aldehydes. The sensing behavior of dicyanovinylcoumarin isomers were studied for different anions. In these dicyanovinylcoumarin isomers, the 7-substituted isomer shows high selectivity towards CN? in the presence of other F?, Cl?, Br?, I?, ClO4?, HSO4? and NO2? ions. The effect of CN? on the structure of dicyanovinylcoumarin isomer was studied by performing DFT calculations. The theoretical calculations show strong agreement with the experimental results. The detection limit for CN? were found to be 1.14 × 10?8 M for 7-substitued dicyanovinylcoumarin isomer 4b.
A one-pot and convenient synthesis of coumarins in solventless system
Shockravi, Abbas,Valizadeh, Hassan,Heravi, Majid M.
, p. 501 - 504 (2003)
An efficient and facile preparation of simple coumarins via in situ Wittig reaction of salicylaldehydes, triphenylphosphine, and chloroethylacetate supported on MgO in satisfactory yields in solvent-free condition.
Synthesis of analogues of natural coumarins and coumarinolignans
Ismailova
, p. 292 - 296 (2005)
3-Aryl-4H-coumarins with the 1,3-benzodioxol, 1,4-benzodioxane, and 1,5-benzodioxepane moieties were synthesized by modified methods.
An expeditious coumarin synthesis via a "Pseudocycloaddition" between salicylaldehydes and ketene
Chandrasekhar, Sosale,Kumar, Honnaiah Vijay
, p. 232 - 235 (2015)
A variety of salicylaldehydes effected tandem nucleophilic addition onto ketene, leading to corresponding coumarins in good yields under mild conditions. This "pseudocycloaddition" represents a very mild variant of the historic Perkin synthesis of coumarin (which remains of key interest in both perfumery and several emerging areas).
Polyphosphoric acid-promoted synthesis of coumarins lacking substituents at positions 3 and 4
Yang, Li-Shou,Wang, Yu,Wang, En-Hua,Yang, Jan,Pan, Xiong,Liao, Xiu,Yang, Xiao-Sheng
, p. 1 - 6 (2020)
Coumarins have recently emerged as a hot topic of research due to their diverse pharmacological properties. This work described a method for the synthesis of 3,4-diunsubstituted coumarins promoted by polyphosphoric acid (PPA) from salicylaldehydes and acetic anhydride. Various coumarins were produced in good to excellent yields.
Synthesis method of coumarin derivatives
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Paragraph 0036-0038, (2020/09/23)
The invention provides a synthesis method of coumarin derivatives. The synthesis method comprises the following steps: adding polyphosphoric acid PPA and a solvent N,N-dimethylformamide DMF, sequentially adding substituted salicylaldehyde and acetic anhydride, and carrying out a heating stirring reaction for 3-6 h under nitrogen protection; and after the reaction is finished, separating and purifying to obtain the coumarin derivative pure products. The synthesis method disclosed by the invention is disclosed for the first time, is short in reaction time, simple to operate, low in catalyst usage amount, cheap, easy to obtain and relatively good in derivative yield, not only provides a new method for synthesizing coumarin derivatives, but also provides more possibilities for large-scale production of products and improvement of production efficiency.
Fe(III)-Catalyzed Decarboxylative C3-Difluoroarylmethylation of Coumarins with α,α-Difluoroarylacetic Acids
Chen, Zhiwei,Bai, Xiang,Sun, Jie,Xu, Yicheng
supporting information, p. 7674 - 7682 (2020/07/15)
A facile Fe(III)-catalyzed oxidative decarboxylative radical coupling reaction of α,α-difluoroarylacetic acids with coumarins has been developed. This transformation, which provides a series of C-3 difluoroarylmethylated coumarins containing various functional groups in moderate-to-good yields, features easily accessible starting materials and operational simplicity.
Unsymmetric Heteroleptic Ir(III) Complexes with 2-Phenylquinoline and Coumarin-Based Ligand Isomers for Tuning Character of Triplet Excited States and Achieving High Electroluminescent Efficiencies
Feng, Zhao,Wu, Yong,Wu, Zhaoxin,Yang, Xiaolong,Yu, Yue,Zhou, Guijiang
supporting information, p. 12362 - 12374 (2020/09/15)
2-Phenylquinoline (PQ) and four coumarin-based ligand isomers with ease of synthesis have been selected to construct the unsymmetric heteroleptic [Ir(C1∧N)(C2∧N)(acac)]-type complex phosphors for organic light-emitting diodes (OLEDs). Six unsymmetric heteroleptic Ir(III) complexes have been obtained by employing four coumarin-based ligand isomers (L-C5/L-C6/L-C7/L-C8) in the [Ir(PQ)(C∧N)(acac)] structure due to two different coordinating carbon atoms in ligands L-C6 and L-C7 to form C-Ir bond. Through adopting unsymmetric heteroleptic [Ir(C1∧N)(C2∧N)(acac)] structure, these Ir(III) complexes can not only achieve impressive absolute quantum yield φp (ca. 0.5-1.0), higher than that of complex [Ir(PQ)2(acac)] (ca. 0.4), but also realize a dual modulation of both emission color from orange (AIrC6out, λ = 578 nm) to red (AIrC5, λ = 622 nm) and the character of the lowest triplet excited states (T1), showing both 3MLCT character and 3ILCT (intraligand charge transfer) character in their T1 states. AIrC5, AIrC7out, and AIrC7in show MLCT character from Ir(III) center to ligand L-C5 or L-C7 and ILCT character in ligand L-C5 or L-C7 in their T1 states, while AIrC6out, AIrC6in, and AIrC8 show MLCT character from Ir(III) center to ligand PQ and ILCT character in ligand PQ in their T1 states. Moreover, the color-tuning mechanism and the lowest triplet state characters are investigated in detail. AIrC6in and AIrC8 were selected as emitters to evaluate the electroluminescent (EL) performance due to their high φP of nearly up to unity. Optimal orange-emitting device B2 based on AIrC8 can give a maximum external quantum efficiency (ηext) of 23.9%, a maximum current efficiency (ηL) of 70.9 cd A-1, and a maximum power efficiency (ηP) of 60.7 lm W-1. All these impressive results can definitely demonstrate the effectiveness of our simple approach for tuning character of the triplet excited states and achieving high-performance Ir-based phosphors in OLEDs.
Visible-light-induced regioselective alkylation of coumarins via decarboxylative coupling with N-hydroxyphthalimide esters
Jin, Can,Yan, Zhiyang,Sun, Bin,Yang, Jin
supporting information, p. 2064 - 2068 (2019/04/11)
An efficient photocatalytic decarboxylative 3-position alkylation of coumarins by using alkyl N-hydroxyphthalimide esters as alkylation reagents has been developed. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) has been proved to be tolerated for this decarboxylation process, affording a broad scope of 3-alkylated coumarin derivatives in moderate to excellent yields. This protocol was highlighted by its mild conditions, readily available starting materials, operational simplicity, and wide functional group tolerance.
Iron-Catalyzed Regioselective Decarboxylative Alkylation of Coumarins and Chromones with Alkyl Diacyl Peroxides
Jin, Can,Sun, Bin,Xu, Tengwei,Yan, Zhiyang,Zhang, Xun
supporting information, p. 1585 - 1591 (2019/08/07)
A facile iron-catalyzed decarboxylative radical coupling of alkyl diacyl peroxides with coumarins or chromones has been developed, affording a highly efficient approach to synthesize a variety of α-alkylated coumarins and β-alkylated chromones. The reaction proceeded smoothly without adding any ligand or additive and provided the corresponding products containing a wide scope of functional groups in moderate to excellent yields. This protocol was highlighted by its high regioselectivity, readily available starting materials, and operational simplicity.
