- A Regioselective Approach to C3-Aroylcoumarins via Cobalt-Catalyzed C(sp 2)-H Activation Carbonylation of Coumarins
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A new cobalt-catalyzed C-H bond activation of coumarins with aryl halides or pseudohalides and carbon monoxide insertion to give various 3-aroylcoumarin derivatives is described. It is the first time that CO as C1 feedstock is used as the coupling partners in cobalt-catalyzed regioselective coumarin C-H functionalization reactions. Upon activation with manganese powder, the Co catalyzes the C-H bond activation carbonylation reactions of aryl iodides, bromides, and even triflates under mild conditions, providing the regioselective aroylated products in moderate to good yields.
- Ansari, Samira,Mirzaei, Siyavash,Pashazadeh, Rahim,Rajai-Daryasarei, Saideh,Shabanian, Meisam,Soheilizad, Mehdi
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supporting information
p. 3014 - 3020
(2019/07/22)
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- A 3 - aryl carbamoyl coumarin derivative synthesis method
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The present invention discloses a preparation method of 3-aryl-formyl coumarin derivatives (I) and (II), and belongs to the field of organic chemistry. According to the method, a substituted coumarin derivative and aryl aldehyde are adopted as raw materia
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Paragraph 0022; 0023; 0024; 0025
(2017/07/04)
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- A Regioselective Metal-Free Construction of 3-Aroyl Coumarins by Csp2-H Functionalization
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A successive metal-free TBHP-mediated regioselective C-H functionalization of coumarins toward expedient synthesis of 3-aroyl coumarins is unveiled. The ongoing method conducted through the reaction of either coumarins or coumarin-3-carboxylic acids with
- Jafarpour, Farnaz,Abbasnia, Masoumeh
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p. 11982 - 11986
(2016/12/09)
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- Regioselective transition metal-free acylation of coumarins via cross-dehydrogenative coupling reaction of coumarins and aldehydes
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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 °C for 8 h regioselectively afforded the corresponding 3-acylcoumarin derivatives in good to excellent yields.
- Adib, Mehdi,Rajai-Daryasarei, Saideh,Pashazadeh, Rahim,Tajik, Mahnaz,Mirzaei, Peiman
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p. 3701 - 3705
(2016/07/26)
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- Regioselective Coupling Reactions of Coumarins with Aldehydes or Di-tert-butyl Peroxide (DTBP) through a C(sp2)-H Functionalization Process
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Coumarin derivatives are highly valuable compounds in drug discovery. Herein, we have developed two new coupling reactions that involve coumarins and either aldehydes or di-tert-butyl peroxide (DTBP) in the presence of inexpensive copper or iron catalysts. Both of these reactions proceed through a C(sp2)-H functionalization process to regioselectivity generate keto- or methyl-substituted coumarin derivatives in moderate to good yields These coupling reactions will enrich current coumarin chemistry.
- Zhao, Wannian,Xu, Lei,Ding, Yingcai,Niu, Ben,Xie, Ping,Bian, Zhaogang,Zhang, Denghong,Zhou, Aihua
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p. 325 - 330
(2016/02/14)
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- Diacylation of coumarins by silver-catalyzed decarboxylative cross-coupling
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A mild silver-catalyzed decarboxylative acylation of coumarins has been developed by using α-oxocarboxylic acids as acyl sources. This protocol provides an efficient and straightforward access to aroyl substituted coumarins in moderate to excellent yields with good selectivities. Furthermore, the reaction conditions were also applicable to quinolinones and naphthoquinones, affording the corresponding acylated heterocyclic compounds.
- Wang, Hua,Zhou, Shi-Liu,Guo, Li-Na,Duan, Xin-Hua
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p. 630 - 636
(2015/02/02)
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- Iron-catalyzed regioselective direct coupling of aromatic aldehydes with coumarins leading to 3-aroyl coumarins
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An efficient protocol for iron-catalyzed cross-coupling of coumarins with aromatic aldehydes has been developed. The various 3-aroyl coumarins were selectively afforded in moderate yields. Some notable features of this protocol are high efficiency, wide f
- Yuan, Jin-Wei,Yin, Qiu-Yue,Yang, Liang-Ru,Mai, Wen-Peng,Mao, Pu,Xiao, Yong-Mei,Qu, Ling-Bo
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p. 88258 - 88265
(2015/11/09)
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- DABCO and Bu3P catalyzed [4 + 2] and [3 + 2] cycloadditions of 3-acyl-2H-chromen-ones and ethyl 2,3-butadienoate
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DABCO-catalyzed [4 + 2] and Bu3P-catalyzed [3 + 2] cycloadditions between 3-acyl-2H-chromen-ones and ethyl 2,3-butadienoate were developed for the synthesis of dihydropyran-fused and cyclopenten-fused chromen-2-ones with high regio- and stereo-
- Wang, Ying,Yu, Zhi-Hua,Zheng, Hu-Fei,Shi, De-Qing
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p. 7739 - 7746
(2013/04/23)
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- An expedient route to highly functionalized 2H-chromene-2-thiones via ring annulation of β-oxodithioesters catalyzed by InCl3 under solvent-free conditions
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A convenient and one-pot synthesis of 3-aroyl/heteroaroyl-2H-chromene-2- thiones and benzo[f]2H-chromene-2-thiones has been developed by the condensation of β-oxodithioesters and salicylaldehydes/α-hydroxynaphthaldehydes in the presence of indium trichlor
- Verma, Rajiv Kumar,Verma, Girijesh K.,Raghuvanshi, Keshav,Singh, Maya Shankar
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p. 584 - 589
(2011/03/18)
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- Condensation of α-aroylketene dithioacetals and 2- hydroxyarylaldehydes results in facile synthesis of a combinatorial library of 3-aroylcoumarins
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A facile, convenient, efficient, and high yielding synthesis of a combinatorial library of 3-aroylcoumarins has been developed by the condensation of easily available α-aroylketene dithioacetals (AKDTAs) and 2-hydroxybenzaldehydes (salicylaldehydes)/2-hydroxy-1-naphthaldehyde in the presence of catalytic amount of piperidine in THF reflux. The condensation of ferrocene derived α-aroylketene dithioacetal and 2-hydroxybenzaldehyde furnished coumarin installed on a ferrocene platform.
- Rao, H. Surya Prakash,Sivakumar
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p. 8715 - 8723
(2007/10/03)
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- FIVE-MEMBERED 2,3-DIOXOHETEROCYCLES. IV. AROYLACETYLATION OF PHENOLS BY 5-ARYL-2,3-DIHYDROFURAN-2,3-DIONES
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Phenyl aroylacetates were obtained by the reaction of phenols and pyrocatechol with 5-aryl-2,3-dihydrofuran-2,3-diones under conditions for the decarbonylation of the latter.The reaction between 5-aryl-2,3-dihydrofuran-2,3-diones and salicylaldehyde and 2-hydroxynapthaldehyde under the same conditions led to the formation of 3-aroyl-2H-chromen-2-ones, 2-(2-aroylacetoxy)phenyl-6-aryl-1,3-dioxin-4-ones, and 3-aroyl-2H-benzochromen-2-ones.
- Andreichikov, Yu. S.,Tokmakova, T. N.
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p. 796 - 800
(2007/10/02)
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