540803-87-0Relevant academic research and scientific papers
Use of Imidazo[1,5-a]pyridin-3-ylidene as a Platform for Metal-Imidazole Cooperative Catalysis: Silver-Catalyzed Cyclization of Alkyne-Tethered Carboxylic Acids
Rawat, Vishal Kumar,Higashida, Kosuke,Sawamura, Masaya
supporting information, p. 1631 - 1637 (2021/02/03)
Silver complexes with 5-(4-(tert-butyl)-1H-imidazol-1-yl)-imidazo[1,5-a]pyridin-3-ylidene ligands were synthesized as metal-imidazole acid-base cooperative catalysts. Single crystal XRD analysis revealed that the silver atom was located in the vicinity of
Gold-catalyzed Rapid Construction of Nitrogen-containing Heterocyclic Compound Library with Scaffold Diversity and Molecular Complexity
Qiao, Jin,Jia, Xiuwen,Li, Pinyi,Liu, Xiaoyan,Zhao, Jingwei,Zhou, Yu,Wang, Jiang,Liu, Hong,Zhao, Fei
, (2019/02/07)
1,3-unsubstituted 2-(1H-indol-2-yl)ethanamines were employed for the first time to react with alkynoic acids (AAs) to achieve gold-catalyzed highly selective cascade reactions to furnish novel indole-fused skeletons. Furthermore, with this powerful gold catalytic system, a library of indole/pyrrole/thiophene/benzene/naphthalene/pyridine-based nitrogen-containing heterocyclic compounds (NCHCs) with scaffold diversity and molecular complexity was constructed rapidly using various amine nucleophiles (ANs) and diverse AAs as the building blocks. This general protocol features excellent selectivity, extraordinarily broad substrate scope, readily available inputs, good to high yields, high bond-forming efficiency, and step economy, thus providing a facile and efficient access to a variety of valuable nitrogen-containing heterocycles.
Gold(I)-Catalysed Cyclisation of Alkynoic Acids: Towards an Efficient and Eco-Friendly Synthesis of γ-, δ- and ?-Lactones
Gasperini, Danila,Maggi, Lorenzo,Dupuy, Stéphanie,Veenboer, Richard M. P.,Cordes, David B.,Slawin, Alexandra M. Z.,Nolan, Steven P.
, p. 3857 - 3862 (2016/12/16)
The improved synthesis of γ-, δ- and ?-lactones using a dinuclear N-heterocyclic carbene (NHC)-gold(I) catalyst is reported. This solvent-free process provides access to γ- and δ-lactones in high regio- and stereoselectivity. Reactions were performed at l
Rhodium(III)-catalyzed intramolecular redox-neutral annulation of tethered alkynes: Formal total synthesis of (±)-goniomitine
Zhou, Bing,Du, Juanjuan,Yang, Yaxi,Li, Yuanchao
supporting information, p. 12768 - 12772 (2015/03/30)
A RhIII-catalyzed intramolecular redox-neutral atom-economic annulation of a tethered alkyne has been developed to efficiently construct 2-amidealkyl indoles with completely reversed regioselectivity by a C-H activation pathway. Furthermore, us
Alkyne-tag Raman imaging for visualization of mobile small molecules in live cells
Yamakoshi, Hiroyuki,Dodo, Kosuke,Palonpon, Almar,Ando, Jun,Fujita, Katsumasa,Kawata, Satoshi,Sodeoka, Mikiko
, p. 20681 - 20689 (2013/02/23)
Alkyne has a unique Raman band that does not overlap with Raman scattering from any endogenous molecule in live cells. Here, we show that alkyne-tag Raman imaging (ATRI) is a promising approach for visualizing nonimmobilized small molecules in live cells. An examination of structure-Raman shift/intensity relationships revealed that alkynes conjugated to an aromatic ring and/or to a second alkyne (conjugated diynes) have strong Raman signals in the cellular silent region and can be excellent tags. Using these design guidelines, we synthesized and imaged a series of alkyne-tagged coenzyme Q (CoQ) analogues in live cells. Cellular concentrations of diyne-tagged CoQ analogues could be semiquantitatively estimated. Finally, simultaneous imaging of two small molecules, 5-ethynyl-2′-deoxyuridine (EdU) and a CoQ analogue, with distinct Raman tags was demonstrated.
Silver-catalyzed intramolecular hydroamination of alkynes in aqueous media: Efficient and regioselective synthesis for fused benzimidazoles
Zhang, Xu,Zhou, Yu,Wang, Hengshuai,Guo, Diliang,Ye, Deju,Xu, Yungen,Jiang, Hualiang,Liu, Hong
, p. 397 - 405 (2011/04/17)
A simple, convenient and green synthetic approach to diverse fused tricyclic benzimidazoles has been developed by Ag(i) complex catalyzed intramolecular hydroamination under the classic method or by microwave irradiation in water. This strategy presents a
An effective synthetic entry to fused benzimidazoles via iodocyclization
Zhang, Xu,Zhou, Yu,Wang, Hengshuai,Guo, Diliang,Ye, Deju,Xu, Yungen,Jiang, Hualiang,Liu, Hong
, p. 1429 - 1437 (2011/08/03)
A protocol for the synthesis of the fused heterocyclic polycyclic compounds pyrrole[1,2-a]benzimidazoles, piperidine[1,2-a]benzimidazoles and oxa-fused benzimidazoles using iodine and silver nitrate by an exo-dig or endo-dig cyclization pathway at room te
Indium tribromide catalyzed cross-Claisen condensation between carboxylic acids and ketene silyl acetals using alkoxyhydrosilanes
Nishimoto, Yoshihiro,Okita, Aya,Yasuda, Makoto,Baba, Akio
supporting information; experimental part, p. 8623 - 8625 (2011/11/06)
Acylations achieved: The title reaction between carboxylic acids and ketene silyl acetals has been accomplished (see scheme). The additive, (MeO) 3SiH, is believed to play an important role in the promotion of the condensation reaction. This reaction system was compatible with a diverse range of functional groups, including alkenes, alkynes, chlorides, alcohols, esters, and nitro groups. Copyright
Cyclization of alkynoic acids with gold catalysts: a surprising dichotomy between AuI and AuIII
Harkat, Hassina,Dembelé, Albert Yénimégué,Weibel, Jean-Marc,Blanc, Aurélien,Pale, Patrick
experimental part, p. 1871 - 1879 (2009/06/28)
ω-Acetylenic acids, substituted or not at their acetylenic end, could be efficiently cyclized to γ- or δ-alkylidene lactones in the presence of AuCl and K2CO3. In contrast AuCl3 led to lactone dimers, probably through cycl
