19725-29-2Relevant academic research and scientific papers
Preparation of 3-acyl-4-arylcoumarins via metal-free tandem oxidative acylation/cyclization between alkynoates with aldehydes
Mi, Xia,Wang, Chenyang,Huang, Mengmeng,Wu, Yusheng,Wu, Yangjie
, p. 148 - 155 (2015)
A new and efficient metal-free tandem acylation/cyclization of alkynoates with aldehydes was developed for the synthesis of 3-acyl-4-arylcoumarins. The reaction was achieved by the addition of acyl radical to alkynes and a C-H bond functionalization to form two new C-C bonds simultaneously.
Visible Light-Induced Decarboxylative Acylarylation of Phenyl Propiolates with α-Oxocarboxylic Acids to Coumarins Catalyzed by Hypervalent Iodine Reagents under Transition Metal-Free Conditions
Yang, Shuai,Tan, Hui,Ji, Wangqin,Zhang, Xiangbiao,Li, Pinhua,Wang, Lei
, p. 443 - 453 (2017)
No Abstract. (Figure presented.).
Photoinduced Generation of Acyl Radicals from Simple Aldehydes, Access to 3-Acyl-4-arylcoumarin Derivatives, and Evaluation of Their Antiandrogenic Activities
Kawaai, Kazuki,Yamaguchi, Tomoaki,Yamaguchi, Eiji,Endo, Satoshi,Tada, Norihiro,Ikari, Akira,Itoh, Akichika
, p. 1988 - 1996 (2018)
A novel photocatalysis to construct the 3-acyl-4-arylcoumarin framework from simple aldehyde with ynoate is described. The reaction proceeded through an acyl radical intermediate generated by hydrogen atom abstraction from aldehyde, followed by reaction with ynoate and then cyclization to afford coumarins. This valuable radical cyclization reaction gave over 20 coumarin derivatives in moderate to good yields with inexpensive 2-tBu-anthraquinone as a catalyst. In addition, synthetic coumarins were investigated for 5α-dihydrotestosterone (DHT)-induced secretion of prostate-specific antigen (PSA) levels and cell proliferation of androgen-dependent CWR22Rv1 cells.
Visible-light-mediated cascade difunctionalization/cyclization of alkynoates with acyl chlorides for synthesis of 3-acylcoumarins
Liu, Yu,Wang, Qiao-Lin,Zhou, Cong-Shan,Xiong, Bi-Quan,Zhang, Pan-Liang,Kang, Shuang-Jian,Yang, Chang-An,Tang, Ke-Wen
, p. 2038 - 2041 (2018)
A new visible-light-mediated radical cyclization of alkynoates with acyl chlorides is described for the one-pot construction of diverse 3-acylcoumarins with high efficiency and selectivity. This method is successful by sequential difunctionalization of an alkynes C–C triple bond with the C–Cl bonds of acyl chloride and aromatic C(sp2)–H bonds. The cyclization is proposed to simultaneously form two new carbon–carbon bonds, and involves radical acylation, 5-exo-trig cyclization, and ester migration.
The visible-light-induced acylation/cyclization of alkynoates with acyl oximes for the construction of 3-acylcoumarins
Chen, Pu,Liu, Yu,Tang, Ke-Wen,Xiong, Bi-Quan,Xiong, Fang-Ting,Zhou, Quan
supporting information, p. 9012 - 9020 (2021/11/04)
A nitrogen-centered radical-mediated carbon-carbon bond cleavage strategy is described to synthesize functionalized 3-acylcoumarins. The strategy is enabled by the visible-light-induced acylation/cyclization of alkynoates with various acyl oxime compounds in acetonitrile. The difunctionalization of carbon-carbon triple bonds precedes the generation of iminyl radicals, which is followed by the formation of acyl radicals. The acyl radicals then attack the carbon-carbon triple bonds, followed by 5-exo-trigcyclization and 1,2-ester migration. This strategy has wide substrate adaptability and good substituent tolerance.
Visible-light-promoted radical acylation/cyclization of alkynoates with aldehydes for the synthesis of 3-acylcoumarins
Wang, Qiumei,Yang, Chao,Jiang, Chao
supporting information, p. 8196 - 8204 (2018/11/23)
A new, efficient, and atom-economic visible-light-promoted radical acylation/cyclization of alkynoates with aldehydes was developed for the synthesis of 3-acylcoumarins. The reaction undergoes a domino radical addition/5-exo cyclization, and ester migration to afford the product in moderate to good yields with wide functional group tolerance. The significant feature of this new method is the excellent tolerance of aliphatic aldehydes, which leads to the efficient synthesis of aliphatic 3-acylcoumarins.
Silver-mediated radical cyclization of alkynoates and α-keto acids leading to coumarins via cascade double c-c bond formation
Yan, Kelu,Yang, Daoshan,Wei, Wei,Wang, Fen,Shuai, Yuanyuan,Li, Qiannan,Wang, Hua
, p. 1550 - 1556 (2015/02/19)
A novel and convenient silver-mediated radical cyclization method for the synthesis of coumarin derivatives via the direct difunctionalization of alkynoates with α-keto acids through double C-C bond formation under mild conditions has been developed. This new method is highly efficient and practical, and the starting materials are readily prepared. The present method should provide a useful strategy for the construction of coumarin motifs.
One-pot synthesis of 3,4-disubstituted coumarins under catalysis of Mn 3O4 nanoparticles
Sun, Huayin,Zhang, Yonghui,Guo, Fengfeng,Yan, Yizhe,Wan, Changfeng,Zha, Zhenggen,Wang, Zhiyong
, p. 480 - 483 (2012/03/09)
The one-pot synthesis of 3,4-disubstituted coumarins from substituted 2-(hydroxymethyl)phenols with β-keto esters catalyzed by Mn 3O4 nanoparticles was developed. A series of 3,4-disubstituted coumarin derivatives were obtained in good yields. A new method for the one-pot synthesis of 3,4-disubstituted coumarins from substituted 2-(hydroxymethyl)phenols with β-keto esters catalyzed by Mn 3O4 nanoparticles has been developed. A series of 3,4-disubstituted coumarin derivatives were synthesized from substituted 2-(hydroxymethyl)phenols and β-keto esters in good yields. Copyright
