27045-21-2Relevant academic research and scientific papers
Rh-Catalyzed Decarbonylative Addition of Salicylaldehydes with Vinyl Ketones: Synthesis of Taccabulins A–E
Rao, Maddali L. N.,Ramakrishna, Boddu S.
, p. 7545 - 7554 (2019/12/15)
A rhodium-catalyzed decarbonylative addition of salicylaldehydes with vinyl ketones was developed to synthesize o-hydroxydihydrochalcones (2-hydroxyphenethyl ketones). These decarbonylative addition reactions afforded various functionalized o-hydroxydihydrochalcones in moderate to good yields with broad functional group tolerance and selectivity. This method was also applied further in the divergent synthesis of dihydrochalcone derived taccabulins A–E.
One-Pot Synthesis of O-Heterocycles or Aryl Ketones Using an InCl3/Et3SiH System by Switching the Solvent
Jia, Wenqiang,Xi, Qiumu,Liu, Tianqi,Yang, Minjian,Chen, Yonghui,Yin, Dali,Wang, Xiaojian
, p. 5141 - 5149 (2019/05/10)
An efficient one-pot synthesis of O-heterocycles or aryl ketones has been achieved using Et3SiH in the presence of InCl3 via a sequential ionic hydrogenation reaction by switching the solvent. This methodology can be used to construct C-O bonds and to prepare conjugate reduction products, including chromans, tetrahydrofurans, tetrahydropyrans, dihydroisobenzofurans, dihydrochalcones, and 1,4-diones in a facile manner. In addition, a novel plausible mechanism involving a conjugate reduction and a tandem reductive cyclization was verified by experimental investigations.
Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: Synthesis of 2-arylchromans
Shang, Xuyang,Zhou, Xiaomeng,Zhang, Wei,Wan, Changfeng,Chen, Junmin
, p. 8187 - 8193 (2015/12/30)
Tosylhydrazine mediated conjugate reduction of 2-hydroxyl chalcones and sequential reductive coupling cyclization is described. This is an unprecedented protocol and an extremely efficient method for a one-pot domino synthesis of 2-arylchromans in good to excellent yields from commercially available, cheap starting materials. More importantly, the two-step reactions can be easily controlled to afford dihydrochalcones or 2-arylchromans by the mole amounts of tosylhydrazine. Furthermore, the operational simplicity of the process and the high functional group tolerance are remarkable.
An unexpected rearrangement-hydration reaction sequence of 2H-chromenes to dihydrochalcones under catalysis of HAuCl4
Maiti, Gourhari,Kayal, Utpal,Karmakar, Rajiv,Bhattacharya, Rudraksha N.
, p. 6321 - 6325,5 (2012/12/12)
2-Aryl-2H-chromenes in aqueous DCM medium under catalysis of HAuCl 4 are converted into 3-(2-hydroxyaryl)-1-arylpropan-1-ones through hydration-rearrangement reaction sequence in very good yield. The key step probably involves the [1,5] hydride shift followed by the hydrolysis under the reaction condition. The notable advantages of this method are operational simplicity and ease of isolation of products and also provide a pathway to convert the chalcone into DHCs with the transposition of carbonyl group. 2012 Elsevier Ltd. All rights reserved.
