15674-78-9Relevant academic research and scientific papers
Synthesis of isoindolo[1,4]benzoxazinone and isoindolo[1,5]benzoxazepine: two new ring systems of pharmaceutical interest
Parrino, Barbara,Ciancimino, Cristina,Carbone, Anna,Spanò, Virginia,Montalbano, Alessandra,Barraja, Paola,Cirrincione, Girolamo,Diana, Patrizia
, p. 7332 - 7338 (2015)
Abstract Two new ring systems, isoindolo[1,4]benzoxazinone and isoindolo[1,5]benzoxazepine, were conveniently synthesized through cyclization of suitably substituted isoindole derivatives. Some of the new compounds exhibited antiproliferative activity aga
Bromination of α-Diazo Phenylacetate Derivatives Using Cobalt(II) Bromide
Wang, Haifeng,Sun, Xiangli,Hu, Manman,Zhang, Xiaoyi,Xie, Lele,Gu, Shuangxi
supporting information, p. 3347 - 3351 (2020/07/04)
A method for the bromination of α-diazo phenylacetate derivatives using cobalt(II) bromide is described. This bromination reaction features a short reaction time, broad substrate scope, operational simplicity, acid-free conditions, and gram-scalability. (Figure presented.).
Synthesis of α,α-disubstituted α-amino esters: Nucleophilic addition to iminium salts generated from amino ketene silyl acetals
Hata, Shingo,Koyama, Hiroshi,Shimizu, Makoto
experimental part, p. 9670 - 9677 (2012/01/04)
Alkoxycarbonyl iminium species are prepared easily by the oxidation of tetrasubstituted amino ketene silyl acetals, and subsequent nucleophilic addition of Grignard reagents to the iminium salts gives α,α- disubstituted α-amino ester derivatives in moderate to good yields, in which aryl and ethynyl substituents are readily introduced.
A one-pot preparation of 5-oxo 2,4-disubstituted 2,5-dihydro-1 H -imidazol-2-carboxylates from α-bromo esters
Ciez, Dariusz,Svetlik, Jan
experimental part, p. 315 - 318 (2011/03/23)
Nucleophilic substitution of a bromine atom by the azide group in aryl- and heteroaryl -α- bromoacetates triggers cascade reactions leading to imidazolin-5-ones formation. The α-azidoacetate intermediates undergo a transformation into non-isolable 2-imino
Lipase-catalyzed enantioselective transesterification toward esters of 2-bromo-tolylacetic acids
Guieysse, David,Salagnad, Christophe,Monsan, Pierre,Remaud-Simeon, Magali
, p. 317 - 323 (2007/10/03)
Lipases from Candida antarctica, Pseudomonas cepacia and Rhizomucor miehei were tested in the resolution of seven racemic substrates belonging to the (RS)-2-bromo tolyl acetate ester category, but differing either in the position of the methyl substituent on the acyl part of the aromatic ring, or in the structure of the alkyl group. Lipase-catalyzed kinetic resolution via transesterification reaction between the ester and octanol in octane revealed that, of the three enzymes tested, P. cepacia lipase is the most efficient for resolution of the various racemates, with R-enantiopreference. In addition, the position of the methyl substituent was found to play a key role in governing the enantioselectivity of the reaction. Using P. cepacia lipase and 2-bromo-m/p-tolyl- or 2-bromophenylacetic acid esters E-values of 6.
A novel palladium-catalyzed homocoupling reaction initiated by transmetallation of palladium enolates
Lei, Aiwen,Zhang, Xumu
, p. 2525 - 2528 (2007/10/03)
Palladium-catalyzed homocoupling reaction of aryl boronic acids has been developed using a protocol similar to the well-documented crosscoupling reaction. α-Halocarbonyl compounds are applied to initiate the reaction via oxidative addition to a palladium(0) species. The resulting palladium enolate halide can promote the double transmetallation. Reductive elimination generates the desire homocoupling product.
Synthesis, biological activity, and SARs of pyrrolobenzoxazepine derivatives, a new class of specific 'peripheral-type' benzodiazepine receptor ligands
Campiani, Giuseppe,Nacci, Vito,Fiorini, Isabella,De Filippis, Maria P.,Garofalo, Antonio,Ciani, Silvia M.,Greco, Giovanni,Novellino, Ettore,Williams, D. Clive,Zisterer, Daniela M.,Woods, Margaret J.,Mihai, Camelia,Manzoni, Cristina,Mennini, Tiziana
, p. 3435 - 3450 (2007/10/03)
The 'peripheral-type' benzodiazepine receptor (PBR) has been reported to play a role in many biological processes. We have synthesized and tested a novel series of PBR ligands based on a pyrrolobenzoxazepine skeleton, in order to provide new receptor ligands. Several of these new compounds proved to be high affinity and selective ligands for PBR, and benzoxazepines 17f and 17j were found to be the most potent ligands for this receptor to have been identified to date. The SAR and the molecular modeling studies detailed herein delineated a number of structural features required for improving affinity. Some of the ligands were employed as 'molecular yardsticks' to probe the spatial dimensions of the lipophilic pockets L1 and L3 in the PBR cleft and to determine the effect of occupation of L1 and L3 with respect to affinity, while other C-7 modified analogues provided information specifically on the hydrogen bonding with a putative receptor site H1. The new pyrrolobenzoxazepines were tested in rat cortex, a tissue expressing high density of mitochondrial PBR, and exhibited IC50 and K(i) values in the low nanomolar or subnanomolar range, as measured by the displacement of [3H]PK 11195 binding. A subset of the highest affinity ligands was also found to have high affinities for [3H]PK 11195 and [3H]Ro 5-4864 binding in rat adrenal mitochondria. All the ligands in this subset are stimulators of steroidogenesis having similar potency and extent of stimulation as PK 11195 and Ro 5-4864 of steroidogenesis in the mouse Y-1 adrenocortical cell line.
Cyclodeshydratation d'aryloxy-2 diaryl-1,2 ethanones en diaryl-2,3 benzofurannes. Influence de la substitution sur la competition entre deux chemins reactionnels
Montfort, Bernard,Laude, Bernard,Vebrel, Joel,Cerutti, Ernest
, p. 848 - 854 (2007/10/02)
Many of the methods for synthesizing derivatives of 2,3-diaryl benzofurans imply cyclodehydration of 1,2-diaryl 2-aryloxyethanones, leading often to a mixture of two isomers which differ by the presence of the aryl substituent at positions C-2 or C-3 of benzofuran.This isomerisation is explained by a competition between two possible mechanisms.Either a direct electrophilic substitution or the intermediate formation of an α-acylcarbenium ion.This study deals with the competition as determined by the substitution of aryl groups in the initial substrate.Each 2,3-diarylbenzofuran was synthesized previously using an unambiguous method.
