120645-73-0Relevant academic research and scientific papers
Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: Synthesis of 2-arylchromans
Shang, Xuyang,Zhou, Xiaomeng,Zhang, Wei,Wan, Changfeng,Chen, Junmin
supporting information, 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.
Concise Synthesis of Dihydrochalcones via Palladium-Catalyzed Coupling of Aryl Halides and 1-Aryl-2-propen-1-ols
Briot, Anne,Baehr, Corinne,Brouillard, Raymond,Wagner, Alain,Mioskowski, Charles
, p. 1374 - 1377 (2007/10/03)
An expedient route to substituted dihydrochalcones is reported. The key step is a palladium-assisted arylation of 1-aryl-2-propen-1-ols. This two-step/one-purification process allows the synthesis of a wide range of compounds with original substitution patterns, including polyphenolic derivatives.
