2717-05-7Relevant articles and documents
Palladium-catalyzed carbonylative cyclization of 2-(2-bromovinyl)benzimidazoles leading to pyrrolone-fused benzimidazoles
Yang, Byeong Woo,Ho, Son Long,Lim, Ho-Jin,Cho, Chan Sik
, p. 83 - 87 (2016)
2-(2-Bromovinyl)benzimidazoles are carbonylatively cyclized under carbon monoxide pressure in toluene in the presence of a catalytic amount of PdCl2 and PPh3 along with a base to give 1H-benzo[d]pyrrolo[1,2-a]imidazolones in good yields.
Understanding the influence of geometric and electronic structure on the excited state dynamical and photoredox properties of perinone chromophores
Castellano, Felix N.,Chakraborty, Arnab,Favale, Joseph M.,Garakyaraghi, Sofia,Palmer, Jonathan R.,Pemberton, Barry C.,Valchar, Mary Katharine,Wells, Kaylee A.,Yarnell, James E.
, p. 24200 - 24210 (2021/11/16)
In this work, a series of eight similarly structured perinone chromophores were synthesized and photophysically characterized to elucidate the electronic and structural tunability of their excited state properties, including excited state redox potentials and fluorescence lifetimes/quantum yields. Despite their similar structure, these chromophores exhibited a broad range of visible absorption properties, quantum yields, and excited state lifetimes. In conjunction with static and time-resolved spectroscopies from the ultrafast to nanosecond time regimes, time-dependent computational modeling was used to correlate this behavior to the relationship between non-radiative decay and the energy-gap law. Additionally, the ground and excited state redox potentials were calculated and found to be tunable over a range of 1 V depending on the diamine or anhydride used in their synthesis (Ered* = 0.45-1.55 V;Eox* = ?0.88 to ?1.67 V), which is difficult to achieve with typical photoredox-active transition metal complexes. These diverse chromophores can be easily prepared, and with their range of photophysical tunability, will be valuable for future use in photofunctional applications.
1,2-Disubstituted Benzimidazoles by the Iron Catalyzed Cross-Dehydrogenative Coupling of Isomeric o-Phenylenediamine Substrates
Foss, Frank W.,Palacios, Philip M.,Pierce, Brad S.,Thapa, Pawan,Tran, Tam
, p. 1991 - 2009 (2020/03/13)
Benzimidazoles are common in nature, medicines, and materials. Numerous strategies for preparing 2-arylbenzimidazoles exist. In this work, 1,2-disubstituted benzimidazoles were prepared from various mono- and disubstituted ortho-phenylenediamines (OPD) by iron-catalyzed oxidative coupling. Specifically, O2 and FeCl3·6H2O catalyzed the cross-dehydrogenative coupling and aromatization of diarylmethyl and dialkyl benzimidazole precursors. N,N′-Disubstituted-OPD substrates were significantly more reactive than their N,N-disubstituted isomers, which appears to be relative to their propensity for complexation and charge transfer with Fe3+. The reaction also converted N-monosubstituted OPD substrates to 2-substituted benzimidazoles; however, electron-poor substrates produce 1,2-disubstituted benzimidazoles by intermolecular imino-transfer. Kinetic, reagent, and spectroscopic (UV-vis and EPR) studies suggest a mechanism involving metal-substrate complexation, charge transfer, and aerobic turnover, involving high-valent Fe(IV) intermediates. Overall, comparative strategies for the relatively sustainable and efficient synthesis of 1,2-disubstituted benzimidazoles are demonstrated.
Imidazole spiro-containing compound and application thereof
-
Paragraph 0207; 0209; 0211, (2020/02/20)
The invention relates to an imidazole spiro-containing compound and an application thereof. The compound has a structural general formula represented by chemical formula (1). The compound has the advantages of good stability, high luminous efficiency, long service life, and simplicity in synthesis.
Cu(OAc)2-Mediated benzimidazole-directed C-H cyanation using 2-(4-methylpiperazin-1-yl)acetonitrile as the cyano source
Zhang, Tianyou,Qiao, Jingyi,Song, He,Xu, Feng,Liu, Xiaochong,Xu, Chunzhao,Ma, Junjie,Liu, Hao,Sun, Zhizhong,Chu, Wenyi
, p. 9084 - 9089 (2019/06/18)
A new protocol for the Cu(OAc)2-mediated cyanation of arenes using benzimidazole as the directing group with 2-(4-methylpiperazin-1-yl)acetonitrile as the cyano source was developed. A series of cyano derivatives were facilely and conveniently obtained in moderate to good yields by using this method. The C-H activation catalytic system was originally applied to the C(sp2)-H cyanation of the aryl/heteroaryl to synthesize 2-(1H-benzo[d]imidazol-2-yl)aryl nitriles. There were 19 new compounds in the synthesized 20 cyanide products. In this reaction, 2-(4-methylpiperazin-1-yl)acetonitrile as the cyano source was originally employed in the C(sp2)-H cyanation of the arenes. In addition, a fluorescent material 5a was obtained by derivative reactions of the obtained cyanide product 3.
The aminocarbonylation of 1,2-diiodoarenes with primary and secondary amines catalyzed by palladium complexes with imidazole ligands
Wójcik, Przemys?aw,Trzeciak, Anna M.
, p. 73 - 83 (2018/05/22)
The efficient carbonylative cyclization of 1,2-diiodobenzene with different primary and secondary amines was performed using a palladium complex with an imidazole ligand, PdCl2(BIM)2, as a catalyst. In reactions performed at 1 atm of CO with primary amines, phthalimides were obtained as the only products with yields of up to 100% in 4 h. An even shorter time, 1 h, was sufficient to obtain the same products employing methyl-2-iodobenzoate as a substrate instead of 1,2-diiodobenzene. In an analogous reaction with secondary amines, 1,2-diiodobenzene was converted to three products, formed in amounts dependent on the reaction conditions. The presence of Pd NPs and soluble palladium intermediates indicated their participation in the catalytic reaction.
Substituted 2-formylbenzoic acids in the synthesis of 11H-isoindolo[2,1-a] benzimidazol-11-ones, 5H-isoindolo[2,1-a][3,1]benzoxazine-5,11(6aH)-diones, and 6,6a-dihydroisoindolo-[2,1-a]quinazoline-5,11-diones
Gromachevskaya,Fin'Ko,Butin,Pushkareva,Strelkov,Isakova,Krapivin
, p. 1331 - 1344 (2014/01/17)
Optimal conditions were developed for the synthesis of 11H-isoindolo[2,1-a] benzimidazol-11-one, 5H-isoindolo[2,1-a][3,1]benzoxazine-5,11(6aH)-dione, and 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives in the reaction of substituted 2-formylbenzoic acids with o-phenylenediamine, anthranilic acid, and anthranilamide, respectively. The bifolded structure of 6,6a- dihydroisoindolo-[1,2-a]quinazoline-5,11-dione was verified and investigated.
Green synthesis of polycyclic benzimidazole derivatives and organic semiconductors
Mamada, Masashi,Perez-Bolivar, Cesar,Anzenbacher, Pavel
scheme or table, p. 4882 - 4885 (2011/12/05)
Polycyclic benzimidazole derivatives, an important class of compounds in organic electronics and photovoltaics, were prepared using a solvent-free "green" process based on heating carboxylic acid anhydrides and arylene diamines in the presence of zinc acetate in the solid state. Products were isolated and purified directly by train sublimation of the crude reaction mixtures. The reaction conditions were optimized using various carboxylic acid anhydrides. Optical and electrochemical properties of these materials are also described.
Kinetic versus thermodynamic access to imidazoisoindolones, benzimidazoisoindolones, and [1,4]diazepinoisoindolones: Intramolecular nitrogen and π-aromatic trapping of N-acyliminium cation
Cul, Armelle,Da?ch, Adam,Decroix, Bernard,Sanz, Gérard,Van Hijfte, Luc
, p. 11029 - 11039 (2007/10/03)
Efficient assembly of substituted imidazo[2,1-a]isoindolones I is reported from suitable α,β-diamine IV (or corresponding β-nitroamine) and phthalic anhydride (1) in a three- or four-step sequence in good yields. The key step of this methodology is based on an intramolecular α-aza- amidoalkylation of the N-acyliminium species. Furthermore, when R2 is an aromatic moiety a competing α-amidoalkylation took place and imidazo[2,1-a]isoindolones (or benzimidazo[2,1-a]isoindolones) I and/or isoindolo[1,4]benzodiazepines III were obtained under kinetic or thermodynamic control. The chemoselectivity of these transformations is also discussed.
A new kinetic model for the acid-catalysed reactions of N-(2-aminophenyl)phthalamic acid in aqueous media
Perry, Christopher J.
, p. 977 - 982 (2007/10/03)
The acid-catalysed breakdown of N-(2-aminophenyl)phthalamic acid has been studied in dilute aqueous acids in the pH range 0-6. The dominant reaction is the formation of N-(2-aminophenyl)phthalimide (between ～80 and ～100% yields in the pH range studied) and its subsequent rearrangement to 2-(2-carboxyphenyl)benzimidazole, occurring as consecutive pseudo-first-order processes. Anomalously, only a minor hydrolysis reaction is observed. A kinetic model for these processes has been constructed and rate constants and activation parameters evaluated. Mechanisms involving pre-equilibria to form the kinetically significant species have been proposed for the consecutive processes. The approach has been adapted to account for the observed kinetics of acid catalysed formation of benzimidazoles from o-aminoanilides.
