73110-71-1Relevant 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.
Tandem Cross Coupling Reaction of Alcohols for Sustainable Synthesis of β-Alkylated Secondary Alcohols and Flavan Derivatives
Shee, Sujan,Paul, Bhaskar,Panja, Dibyajyoti,Roy, Bivas Chandra,Chakrabarti, Kaushik,Ganguli, Kasturi,Das, Ayan,Das, Gourab Kanti,Kundu, Sabuj
supporting information, p. 3888 - 3893 (2017/10/07)
A Ru(II) NHC complex (loading down to 0.001 mol%) catalyzed cross coupling of a broad range of aromatic, aliphatic and heterocyclic alcohols is reported. This protocol also functioned efficiently under solvent-free conditions. Remarkably, this catalytic system disclosed so far the highest TON of 288000 for the cross coupling of alcohols. Notably, this methodology was successfully applied for the one-pot synthesis of a range of flavan derivatives. A detailed DFT studies and kinetic experiments were performed to understand the reaction mechanism as well as the high reactivity of this catalytic system. (Figure presented.).
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.
Transition metals catalyzed C-C and C-O bonds formation: Facile synthesis of flavans and benzoxepines
Ramulu, B. Venkat,Mahendar,Krishna,Reddy, A. Gopi Krishna,Suchand,Satyanarayana
, p. 8305 - 8315 (2013/09/02)
A simple and practical method has been developed based on intermolecular [Pd]-catalyzed C-C and an intramolecular [Cu]-catalyzed C-O bond formations for the synthesis of flavans and benzoxepines. Interestingly, the method is amenable for the synthesis of
An efficient intermolecular [Pd]-catalyzed C-C and intramolecular [Cu]-catalyzed C-O bonds formation: Synthesis of functionalized flavans and benzoxepine
Suchand,Krishna,Venkat Ramulu,Dibyendu,Gopi Krishna Reddy,Mahendar,Satyanarayana
, p. 3861 - 3864 (2012/08/14)
An efficient three-step strategy for the synthesis of functionalized flavans, starting from readily available 2-bromoiodobenzenes and aryl vinyl alcohols, is presented and successfully extended to benzoxepine. An intermolecular [Pd]-catalyzed C-C and an i
An efficient synthesis of flavans from salicylaldehyde and acetophenone derivatives
Mazimba, Ofentse,Masesane, Ishmael B.,Majinda, Runner R.
, p. 6716 - 6718 (2012/01/02)
An efficient total synthesis of flavans from the reactions of salicylaldehyde and acetophenone derivatives is reported. The synthesis involves preparation of chalcones through an aldol reaction followed by reduction of both the double bond and the ketone using NaBH4 and an acetic acid mediated cyclization. Methoxy groups on the aromatic rings did not affect significantly the yields of the procedure.
Reduction of flavanones by NaBH3CN in trifluoroacetic acid.
Lewin, G.,Bert, M.,Dauguet, J. C.,Dolley, J.,Menez, P. Le,et al.
, p. 939 - 944 (2007/10/02)
For our studies on the reduction of flavanones, we worked on flavanone itself and on some other derivatives, oxygenated on the B ring.Besides expected flavans and chalcanes, condensed compounds (dimers and trimers) are also obtained.Reaction begins with the reduction of carbonyl to methylene; all the other isolated products arise from the two possible and competitive reactions on the potential carbocation C-2 of the flavan system: a) reductive cleavage of heterocycle; b) electrophilic aromatic substitution.Reactivity of flavanones is correlated with substituents of B ring through their ?+ values. Key words: flavanones / sodium cyanoborhydride / trifluoroacetic acid / flavans / chalcanes / dimers
