59749-78-9Relevant academic research and scientific papers
[Pd]-Catalyzed Intermolecular Coupling and Acid Mediated Intramolecular Cyclodehydration: One-Pot Synthesis of Indenes
Niharika, Pedireddi,Satyanarayana, Gedu
, p. 971 - 979 (2018/02/22)
An efficient one-pot synthesis of indenes from simple starting materials is presented. This process involves a dual C–C bond formation through an intermolecular Heck coupling reaction followed by acid-mediated intramolecular cyclodehydration. The strategy
Superacid-Mediated Intramolecular Cyclization/Condensation: Facile One-Pot Synthesis of Spirotetracyclic Indanones and Indenes
Ramulu, Bokka Venkat,Kumar, Devarapalli Ravi,Satyanarayana, Gedu
, p. 2179 - 2183 (2017/09/26)
A facile, superacid-promoted, domino, one-pot synthesis of novel spirotetracyclic indanones through intramolecular Friedel-Crafts acylation/alkylation of α,β-unsaturated cinnamic acid esters is presented. Interestingly, when the β-aryl group contained ele
Rhodium(II)- or Copper(I)-Catalyzed Formal Intramolecular Carbene Insertion into Vinylic C(sp2)?H Bonds: Access to Substituted 1H-Indenes
Zhou, Qi,Li, Shichao,Zhang, Yan,Wang, Jianbo
supporting information, p. 16013 - 16017 (2017/11/27)
A rhodium(II)- or copper(I)-catalyzed formal intramolecular carbene insertion into vinylic C(sp2)?H bonds is reported herein. This method provides straightforward access to 1H-indenes with high efficiency and excellent functional-group compatibility. Mechanistically, the reaction is proposed to involve the following sequence: metal carbene formation, intramolecular nucleophilic addition of the double bond to the electron-deficient carbene carbon atom, dearomatization, and finally a 1,5-H shift.
Palladium-Catalyzed Formal [4 + 1] Annulation via Metal Carbene Migratory Insertion and C(sp2)-H Bond Functionalization
Xu, Shuai,Chen, Ri,Fu, Zihao,Zhou, Qi,Zhang, Yan,Wang, Jianbo
, p. 1993 - 1997 (2017/08/14)
A highly efficient and operationally simple palladium-catalyzed formal [4 + 1] annulation reaction has been developed. The reaction is featured by the formation of two different C-C bonds on a carbenic center. It represents a concise method for the synthesis of a wide range of polycyclic aromatic hydrocarbons (PAHs) and 1H-indenes with easily available (trimethylsilyl)diazomethane as the carbene source. Metal carbene migratory insertion and C(sp2)-H bond activation are proposed as the key steps in this transformation. The reaction further demonstrates the versatility of the carbene-based coupling in combination with various transition-metal-catalyzed transformations.
Synthesis of indenes via aluminum chloride-promoted tandem Friedel-Crafts alkylation of arenes and cinnamaldehydes
Kheira, Haiouani,Li, Pingfan,Xu, Jiaxi
, p. 168 - 174 (2014/06/09)
A series of substituted indenes were synthesized from arenes and cinnamaldehydes via aluminum chloride-promoted tandem Friedel-Crafts alkylation. The scope and limitation of the tandem reaction were explored. A plausible reaction mechanism is also discuss
Friedel-crafts-type cyclodehydration of 1,3-diphenyl-1-propanones. Kinetic evidence for the involvement of dication
Saito, Shinichi,Sato, Yasuo,Ohwada, Tomohiko,Shudo, Koichi
, p. 2312 - 2317 (2007/10/02)
The mechanism of intramolecular ketone-aromatic cyclodehydration of 1,3-diphenyl-1-propanones to give 1-phenyl-1H-indenes in trifluoromethanesulfonic acid (TFSA) was investigated. The rate of the reaction of the monoprotonated diphenylpropanone increased
Palladium-Catalyzed Coupling of Arylstannanes with Organic Sulfonates: A Comprehensive Study
Farina, Vittorio,Krishnan, Bala,Marshall, Daniel R.,Roth, Gregory P.
, p. 5434 - 5444 (2007/10/02)
The effect of ligands and lithium chloride on the rates of the palladium catalyzed coupling between organic triflates and arylstannanes was studied.The dependence of the rate on the ligand is similar to the one previously reported for the coupling of vinylstannanes, but in the present case triphenylarsine is shown to be superior to both triphenylphosphine and tri(2-furyl)phosphine.The effect of added chloride is complex and varies depending on solvent and ligand used.Ortho-substituted arylstannanes tend to transfer alkyl moieties to a substantial extent, andtherefore rates and efficiencies of aryl vs alkyl transfer were quantitated.When ortho substituents that are potentially coordinating to tin are used, no rate acceleration in the alkyl transfer process was observed, which is in contrast with two recently reported studies that suggest nucleophilic assistance at tin to be important in the transmetalation step.An important side reaction in the coupling of poorly reactive vinyltriflates and most aryltriflates is the Pd-induced homocoupling of the stannane to form biaryls.The experimental factors that control this process were evaluated.
Synthesis of clozapine analogues and their affinity for clozapine and spiroperidol binding sites in rat brain
de Paulis,Betts,Smith,Mobley,Manier,Sulser
, p. 1021 - 1026 (2007/10/02)
Analogues of clozapine, some prepared by a novel, shorter synthesis than those described previously, were evaluated as potential antipsychotic agents using clozapine binding sites in rat forebrain that are nonmuscarinic and nondopaminergic in nature and f
