132628-76-3Relevant academic research and scientific papers
Efficient synthesis of selected phthalazine derivatives
Bunce, Richard A.,Harrison, Todd,Nammalwar, Baskar
, p. 123 - 126 (2012)
Four phthalazine derivatives have been prepared from substituted 2-bromobenzaldehyde acetals by a sequence involving: (1) lithiation and formylation; (2) deprotection; and (3) condensative cyclization with hydrazine. Two additional phthalazines were prepa
Synthesis of Cyclopropanoids via Substrate-Based Cyclization Pathways
Mishra, Uttam K.,Patel, Kaushalendra,Ramasastry
supporting information, p. 175 - 179 (2019/01/04)
A series of unexpected reactions triggered by the dimethyloxosulfonium methylide led to the discovery of unconventional approaches for the synthesis of cyclopropa-fused tetralones and indeno-spirocyclopropanes. These highly functionalized structures were further elaborated in one step to privileged scaffolds such as tetralones, indenones, and fluorenones. As a whole, the results presented herein establish new diversity-oriented folding pathways.
Catalytic Dibenzocyclooctene Synthesis via Cobalt(III)–Carbene Radical and ortho-Quinodimethane Intermediates
te Grotenhuis, Colet,van den Heuvel, Naudin,van der Vlugt, Jarl Ivar,de Bruin, Bas
supporting information, p. 140 - 145 (2017/12/13)
The metalloradical activation of ortho-benzallylaryl N-tosyl hydrazones with [Co(TPP)] (TPP=tetraphenylporphyrin) as the catalyst enabled the controlled exploitation of the single-electron reactivity of the redox non-innocent carbene intermediate. This method offers a novel route to prepare eight-membered rings, using base metal catalysis to construct a series of unique dibenzocyclooctenes through selective Ccarbene?Caryl cyclization. The desired eight-membered-ring products were obtained in good to excellent yields. A large variety of aromatic substituents are tolerated. The proposed reaction mechanism involves intramolecular hydrogen atom transfer (HAT) to CoIII–carbene radical intermediates followed by dissociation of an ortho-quinodimethane that undergoes 8π cyclization. The mechanism is supported by DFT calculations, and the presence of radical-type intermediates was confirmed by trapping experiments.
Water-soluble isoindolo[2,1-a]quinoxalin-6-imines: In vitro antiproliferative activity and molecular mechanism(s) of action
Parrino, Barbara,Carbone, Anna,Ciancimino, Cristina,Spanò, Virginia,Montalbano, Alessandra,Barraja, Paola,Cirrincione, Girolamo,Diana, Patrizia,Sissi, Claudia,Palumbo, Manlio,Pinato, Odra,Pennati, Marzia,Beretta, Giovanni,Folini, Marco,Matyus, Peter,Balogh, Balázs,Zaffaroni, Nadia
, p. 149 - 162 (2015/03/18)
Water-soluble isoindoloquinoxalin (IIQ) imines and the corresponding acetates were conveniently prepared from the key intermediates 2-(2′-aminophenyl)-2H-isoindole-1-carbonitriles obtained by a Strecker reaction between substituted 1,2-dicarbaldehydes and 1,2-phenylenediamines. Both series were screened by the National Cancer Institute (Bethesda, MD) and showed potent antiproliferative activity against a panel of 60 human tumor cell lines. Several of the novel compounds showed GI50 values at a nanomolar level on the majority of the tested cell lines. Among IIQ derivatives, methoxy substituents at positions 3 and 8 or/and 9 were especially effective in impairing cell cycle progression and inducing apoptosis in cancer cells. These effects were associated to IIQ-mediated impairment of tubulin polymerization at pharmacologically significant concentrations of tested compounds. In addition, impaired DNA topoisomerase I functions and perturbation in telomere architecture were observed in cells exposed to micromolar concentrations of IIQ derivatives. The above results suggest that IIQ derivatives exhibit multi-target cytotoxic activities.
PENTAARYLBIIMIDAZOLE COMPOUND AND METHOD FOR PRODUCING THE COMPOUND
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Paragraph 0057; 0059, (2018/10/10)
PROBLEM TO BE SOLVED: To provide an industrially usable photochromic compound which solves problems of a conventional photochromic material that the material is insufficient in terms of coloring and decoloring speeds and durability, and that there are man
Pentaarylbiimidazole, PABI: An easily synthesized fast photochromic molecule with superior durability
Yamashita, Hiroaki,Abe, Jiro
supporting information, p. 8468 - 8471 (2014/07/22)
We report a new type of fast photochromic imidazole dimer, pentaarylbiimidazole (PABI), which shows a few μs fast photochromism with high fatigue resistance against light irradiation. PABI has an unusual spiroconjugated imidazoisoindole skeleton and its d
Organocatalytic, Enantioselective, intramolecular oxa-michael reaction of alkoxyboronate: A new strategy for enantioenriched 1-substituted 1,3-Dihydroisobenzofurans
Ravindra, Barnala,Das, Braja Gopal,Ghorai, Prasanta
supporting information, p. 5580 - 5583 (2015/02/19)
An unprecedented strategy for the synthesis of enantioenriched 1-substituted 1,3-dihydroisobenzofurans via an enantioselective oxa-Michael reaction of o-alkoxyboronate containing chalcone (II) has been accomplished employing cinchona alkaloid based squara
One-pot syntheses of isoquinolin-3-ones and benzo-1,4-diazepin-2,5-diones utilizing Ugi-4CR post-transformation strategy
Che, Chao,Li, Song,Yu, Zhixiong,Li, Fangfang,Xin, Shengchang,Zhou, Liyan,Lin, Shuo,Yang, Zhen
supporting information, p. 202 - 207 (2013/05/09)
One-pot and efficient syntheses of structurally diverse isoquinolin-3-ones and isoquinolin-3-one-based benzo-1,4-diazepin-2,5-diones have been developed. The notable features of the process include the Ugi condensation of monomasked phthalaldehydes with a
Vinyl Azides in Heterocyclic Synthesis. Part 10. Synthesis of the Isoindolobenzazepine Alkaloid Lennoxamine
Moody, Christopher J.,Warrellow, Graham J.
, p. 2929 - 2936 (2007/10/02)
A total synthesis of the isoindolobenzazepine alkaloid lennoxamine (1), by a route involving vinyl azide chemistry, is described.Model studies on the azidocinnamates (12) and (13) revealed a striking difference between the (E)- and (Z)-isomers; whereas the (Z)-isomer (12) gave largely the 1-benzylisoquinoline (15) on decomposition, the (E)-isomer (13) gave the 2-aryl-3-benzazepine (14) as the major product.Consequently, in the lennoxamine synthesis, the azidocinnamate (26) bearing the (E)-alkenyl side chain, prepared from 6-bromopiperonal via the (E)-stilbene aldehyde (25) (Scheme 4), was decomposed to give the key 2-aryl-3-benzazepin e (27).Reduction of the double bonds in (27) was accompanied by cyclisation to the tetrahydroisoindolobenzazepine (30), which was converted into lennoxamine (1) by reduction of the ester group to an aldehyde, and decarbonylation.
