- Palladium-catalyzed synthesis of 8-allyl or 8-prenylcoumarins by using organotin reagents as multicoupling nucleophiles
-
In this study, 8-iodocoumarin derivatives underwent a direct Stille cross-coupling reaction with several organotin compounds in the presence of a catalytic amount of Pd(PPh3)4 in DMF at 80 °C. The cross-coupling reaction proceeded smoothly under mild conditions and permitted the formation of 8-allyl or 8-prenylcoumarin compounds in good yields. Copyright
- Yin, Qiang,Yan, Han,Zhang, Yaqin,Wang, Yige,Zhang, Guojin,He, Yuxiang,Zhang, Weihua
-
-
Read Online
- Practical, Large-Scale Preparation of Benzoxepines and Coumarins through Rhodium(III)-Catalyzed C-H Activation/Annulation Reactions
-
Herein we disclose the assembly of benzoxepines and coumarins from 2-alkenylphenol precursors using [Cp*RhCl2]2 as the precatalyst and alkynes or carbon monoxide as reacting partners. The preparation of benzoxepines and coumarins can be scaled up to 33 mmol using low catalyst loadings.
- Gulías, Moisés,Marcos-Atanes, Daniel,Mascare?as, José L.,Font, Marc
-
supporting information
p. 1669 - 1673
(2019/09/04)
-
- Microwave-Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol
-
Herein we describe a one-pot microwave-assisted method for the synthesis of cinnamic acid and coumarin derivatives. The synthesis begins with an aldehyde synthon, and the chosen reaction conditions determine whether a cinnamic acid or coumarin derivative is formed. A regioselective Claisen rearrangement was also efficiently incorporated into the synthetic sequence to further increase the complexity of the product. Notably, this approach provides high product yields and selectivities without the need of a phenol protecting group.
- Konrádová, Daniela,Kozubíková, Hana,Dole?al, Karel,Pospí?il, Ji?í
-
p. 5204 - 5213
(2017/09/29)
-
- Synthesis of Allyl- and Prenylcoumarins via Microwave-Promoted Tandem Claisen Rearrangement/Wittig Olefination
-
Allyl, dimethylallyl, crotyl, and prenyl ethers of various aromatic ortho-hydroxy carbonyl compounds undergo a tandem sequence of Claisen rearrangement, carbonyl olefination, and cyclization upon microwave irradiation in the presence of a stabilized ylide. The products are multiply substituted 6- or 8-allylated or prenylated coumarins (2H-chromen-2-ones).
- Schmidt, Bernd,Riemer, Martin
-
p. 141 - 149
(2015/12/26)
-
- Synthesis of osthole derivatives with grignard reagents and their larvicidal activities on mosquitoes
-
The structure of osthole has been modified to improve its larvicidal activity against mosquitoes. A new efficient synthesis of osthole derivatives with Grignard reagents has been developed, which employs CuI and LiCl as promoters and covers a broad range of substrates to afford the corresponding products in mild to good yields (up to 83%). Bio-activity evaluation showed that several products exhibited better activities than osthole. CuI and LiCl promoted efficient synthesis of osthole derivatives with Grignard reagents has been developed. Bio-activity evaluation showed that several products exhibited far better larvicidal activities against mosquitoes than osthole.
- Liu, Ming,Liu, Yang,Hua, Xuewen,Wu, Changchun,Zhou, Sha,Wang, Baolei,Li, Zhengming
-
p. 1353 - 1358
(2016/02/18)
-
- Synthesis and anthelmintic activity of osthol analogs against Dactylogyrus intermedius in goldfish
-
In an attempt to develop novel anthelmintic agents, our previously isolated osthol was used as lead structures for further optimization. In our research, a series of coumarin analogs, prepared from 7-hydroxy coumarin or 7-hydroxy-4-methyl coumarin, have been evaluated for their anthelmintic activities. In all of the compounds, 6 and 7 were first synthesized, and their structures were identified based on NMR and MS values. Among the candidates, 8-allyl-7-allyloxycoumarin showed better anthelmintic activity than other compounds against Dactylogyrus infestation with EC50 value of 1.81 mg/L. The quantitative structure-activity relationship (QSAR) of 16 osthol analogs with anthelmintic activity expressed as pEC50 and toxicity to goldfish expressed pLC50, such results can offer useful theoretical references for future experimental works.
- Liu, Guang-Lu,Hao, Bing,Liu, Shao-Peng,Wang, Gao-Xue
-
p. 582 - 590
(2012/09/11)
-