85510-69-6Relevant academic research and scientific papers
Palladium catalyzed carbonylative generation of potent, pyridine-based acylating electrophiles for the functionalization of arenes to ketones
Arndtsen, Bruce A.,Kaiser, Angela M.,Liu, Yi
, p. 8610 - 8616 (2020/09/07)
We describe here the design of a palladium catalyzed route to generate aryl ketones via the carbonylative coupling of (hetero)arenes and aryl- or vinyl-triflates. In this, the use of the large bite angle Xantphos ligand on palladium provides a unique avenue to balance the activation of the relatively strong C(sp2)-OTf bond with the ultimate elimination of a new class of potent Friedel-Crafts acylating agent: N-acyl pyridinium salts. The latter can be exploited to modulate reactivity and selectivity in carbonylative arene functionalization chemistry, and allow the efficient synthesis of ketones with a diverse array of (hetero)arenes. This journal is
An Electrophilic Approach to the Palladium-Catalyzed Carbonylative C-H Functionalization of Heterocycles
Tjutrins, Jevgenijs,Arndtsen, Bruce A.
supporting information, p. 12050 - 12054 (2015/10/05)
A palladium-catalyzed approach to intermolecular carbonylative C-H functionalization is described. This transformation is mediated by PtBu3-coordinated palladium catalyst and allows the derivatization of a diverse range of heterocycles, including pyrroles, indoles, imidazoles, benzoxazoles, and furans. Preliminary studies suggest that this reaction may proceed via the catalytic formation of highly electrophilic intermediates. Overall, this provides with an atom-economical and general synthetic route to generate aryl-(hetero)aryl ketones using stable reagents (aryl iodides and CO) and without the typical need to exploit pre-metalated heterocycles in carbonylative coupling chemistry.
Synthesis and in vitro characterization of cinnoline and benzimidazole analogues as phosphodiesterase 10A inhibitors
Yang, Hao,Murigi, Francis N.,Wang, Zhijian,Li, Junfeng,Jin, Hongjun,Tu, Zhude
supporting information, p. 919 - 924 (2015/02/19)
Fifteen cinnoline analogues and six benzimidazole phosphodiesterase 10A (PDE10A) inhibitors were synthesized as potential PET radiopharmaceuticals and their in vitro activity as PDE10A inhibitors was determined. Nine out of twenty-one compounds were potent inhibitors of PDE10A with IC50 values ranging from 1.5 to 18.6 nM. Notably, the IC50 values of compounds 26a, 26b, and 33c were 1.52 ± 0.18, 2.86 ± 0.10, and 3.73 ± 0.60 nM, respectively; these three compounds also showed high in vitro selectivity (>1000-fold) for PDE10A over PDE 3A/3B, PDE4A/4B. The high potency and selectivity of these three compounds suggests that they could be radiolabeled with PET radionuclides for further evaluation of their in vivo pharmacological behavior and ability to quantify PDE10A in the brain.
Palladium-catalyzed carbonylative C-H activation of heteroarenes
Wu, Xiao-Feng,Anbarasan, Pazhamalai,Neumann, Helfried,Beller, Matthias
supporting information; experimental part, p. 7316 - 7319 (2010/11/05)
Not only carbonylation: The first carbonylative cross-coupling reactions towards ketones using C-H activation have been developed. Various heteroarenes, such as oxazoles, thiazoles, and imidazoles were used as coupling partners in this methodology. DBU =
Nucleophilic Acylation of Benzimidazole
Khristich, B. I.,Simonov, A. M.,Shepelenko, E. N.,Yatsimirskii, V. A.
, p. 87 - 90 (2007/10/02)
Conditions that make it possible to realize the direct C(2) acylation of benzimidazole and some of its derivatives were found.It is shown that bis products, which are converted to 2-acylbenzimidazoles upon heating to 140-200 deg C with acyl halides in the
