27045-21-2Relevant academic research and scientific papers
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.
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.
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.
