26466-19-3Relevant academic research and scientific papers
Synthesis of β,β-disubstituted indanones via the Pd-catalyzed tandem conjugate addition/cyclization reaction of arylboronic acids with α,β-unsaturated esters
Gao, Ang,Liu, Xiu-Yan,Li, Hao,Ding, Chang-Hua,Hou, Xue-Long
, p. 9988 - 9994 (2018/05/31)
Under Pd catalysis with a newly synthesized electron-deficient heterocycle, 2-(4,5-dihydroimidazol-2-yl)- pyrimidine (as the ligand), the reaction of α,β-unsaturated esters with arylboronic acids afforded a wide range of 3,3-disubstituted indan-1-ones bearing a quaternary carbon in high yields. Mechanistic studies revealed that the reaction involves a tandem conjugate addition/1,4-Pd shift followed by a cyclization.
Superacid mediated intramolecular condensation: Facile synthesis of indenones and indanones
Ramulu, Bokka Venkat,Satyanarayana, Gedu
, p. 70972 - 70976 (2015/09/08)
Superacid promoted intramolecular acylation is described for the synthesis of indenones. Interestingly, in all resulting indenones, the olefin bond is rearranged to the exo position of the five membered rings. Significantly, the method is further applied to the synthesis of indanones via the formation of two C-C bonds by in situ treatment of indenones with an external arene, in one-pot. Most importantly, the present sequential method for the synthesis of indanones is advantageous, as it limits even more electron rich external arenes only to the Friedel-Crafts alkylation. This is not possible in previous reports wherein both cinnamic acid ester and the external arenes are treated together in the presence of an acid, wherein the relatively more reactive arene is preferred to facilitate the acylation step.
A rhodium(I)-catalysed formal intramolecular C-C/C-H bond metathesis
Matsuda, Takanori,Yuihara, Itaru
, p. 7393 - 7396 (2015/04/27)
Phenylcyclobutanes underwent skeletal reorganisation in the presence of Wilkinson's catalyst to afford indanes through a cascade process involving chelation-assisted C-C bond cleavage and intramolecular C-H bond cleavage.
Indium-catalyzed, novel route to β,β-disubstituted indanones via tandem Nakamura addition-hydroarylation-decarboxylation sequence
Rajesh, Nimmakuri,Prajapati, Dipak
supporting information, p. 3347 - 3350 (2015/03/18)
A novel method for the construction of β,β-disubstituted indanones has been developed via tandem Nakamura addition-hydroarylation-decarboxylation process. Indium(iii) triflate was demonstrated as a versatile multitasking catalyst, which catalyzes three different chemical transformations under one-pot conditions. This journal is
Rhodium-catalysed arylative annulation of 1,4-enynes with arylboronic acids
Matsuda, Takanori,Watanuki, Shoichi
supporting information, p. 702 - 705 (2015/02/19)
The rhodium(I)-catalysed arylative annulation of 1,4-enynes with arylboronic acids was investigated. The reaction was found to proceed via an addition-1,4-rhodium migration-addition sequence, affording the corresponding 1,1-disubstituted 3-(arylmethylene)indanes.
Superacid-promoted dual C-C bond formation by Friedel-Crafts alkylation and acylation of ethyl cinnamates: Synthesis of indanones
Venkat Ramulu, Bokka,Gopi Krishna Reddy, Alavala,Satyanarayana, Gedu
supporting information, p. 868 - 872 (2013/05/22)
A superacid (triflic acid) promoted dual C-C bond formation via intermolecular Friedel-Crafts alkylation (Michael addition type) and intramolecular acylation for the efficient synthesis of 3-substituted indan-1-ones is presented. This method was successful in activating ethyl cinnamates towards dual aromatic electrophilic substitution. Moreover, it enabled us to synthesize novel spirotetracyclic systems. Georg Thieme Verlag Stuttgart · New York.
Superacid-Catalyzed Reactions of Cinnamic Acids and the Role of Superelectrophiles
Rendy, Rendy,Zhang, Yun,McElrea, Aaron,Gomez, Alma,Klumpp, Douglas A.
, p. 2340 - 2347 (2007/10/03)
The chemistry of cinnamic acids and related compounds has been studied. In superacid-catalyzed reactions with arenes, two competing reaction mechanisms are proposed. Both mechanisms involve the formation of dicationic intermediates (superelectrophiles), and the reactions can lead to either chalcone-type products or indanone products. The direct observation of a dicationic species (by low-temperature 13C NMR) is reported. We provide clear evidence that protonated carboxylic acid groups (or the corresponding acyl cation) can enhance the reactivity of an adjacent electrophilic center. Triflic acid is also found to be an effective acid catalyst for the direct synthesis of some electron-deficient chalcones and heterocyclic chalcones from cinnnamic acids.
Routes to 3aH-Indenes. Deprotonation and Methylation of some Indenones Bearing Ring Junction Substituents
Gilchrist, Thomas L.,Rees, Charles W.,Tuddenham, David
, p. 3221 - 3224 (2007/10/02)
The trienones (1), (2), and (3) have been converted into the corresponding enolate anions by reaction with potassium hydride below -10 deg C.Methyl fluorosulphonate was added to each solution: with the trienones (1) and (3), transient 3aH-indenes (4a) and
