13636-88-9Relevant academic research and scientific papers
Stereochemistry controlled by an asymmetric sulfur atom, and a rare example of a kryptoracemate
Bouamaied, Imenne,Constable, Edwin C.,Housecroft, Catherine E.,Neuburger, Markus,Zampese, Jennifer A.
, p. 10276 - 10285 (2012)
The ligands 4-methylthio-6-phenyl-2,2′-bipyridine (1) and the corresponding sulfoxide (2) and sulfone (3) have been synthesized and characterized in solution, and in the solid state by single crystal X-ray diffraction. Compounds 2 and 3 crystallize in the same space group (C2/c) with similar unit cell parameters; a small increase in the unit cell volume allows for the presence of the extra oxygen atom in 3. The sulfoxide and sulfone groups adopt conformations that permit intramolecular O...HCaryl hydrogen bonds. The complexes [Ir(ppy)2L][PF6] with L = 1, 2 or 3 have been prepared and characterized. The asymmetric sulfur atom in ligand 2 gives rise to pairs of diastereoisomers of the complex which can be distinguished in the 1H and 13C NMR spectra. In solution, exchange of [PF6]- by [Δ-TRISPHAT]- gives rise to four diastereoisomers and we observed good dispersion of 1H NMR resonances, especially for those assigned to protons close to the asymmetric sulfur atom. A single crystal X-ray diffraction study of 2{[Ir(ppy) 2(3)][PF6]}·CHCl3·3H 2O reveals that the complex crystallizes in the chiral space group P212121, the asymmetric unit containing crystallographically independent Δ- and Λ-[Ir(ppy) 2(3)]+ cations. This provides a rare example of a so-called kryptoracemate in the solid state. In MeCN solution, [Ir(ppy) 2(1)][PF6], [Ir(ppy)2(2)][PF6] and [Ir(ppy)2(3)][PF6] are weakly emissive (λem = 600, 647 and 672 nm, respectively) and preliminary studies of the electroluminescent properties of [Ir(ppy)2(2)][PF 6] indicate that the complexes are not suitable candidates for LECs.
Bronsted acid catalyzed PhSe transfer versus radical aryl transfer: Linear codimerization of styrenes and internal olefins
Wu, Ping,Wang, Liandi,Wu, Kaikai,Yu, Zhengkun
, p. 868 - 871 (2015)
Bronsted acid p-TsOH·H2O-catalyzed hydrovinylation of styrenes with internal olefins α-oxo ketene dithioacetals was efficiently achieved in the presence of N-phenylselenophthalimide (N-PSP), regioselectively affording Markovnikov phenylselenati
Evaluation of [12C/11C]carbon monoxide binding to copper(I) tris(pyrazolyl)borate complexes
Kealey, Steven,White, Andrew J.P.,Gee, Antony D.,Long, Nicholas J.
, p. 1896 - 1905 (2014)
The copper(I) coordination chemistry of tris(3-R-5-R′-pyrazolyl) borate ligands (TpR,R′) bearing substituent groups attached to the pyrazole rings has been investigated under nitrogen and carbon monoxide atmospheres [1 (TpPh,SMe) R =
One-Pot Mitsunobu Protocol to Access Ketene S,S-/N,S-Acetals at Room Temperature
Saha, Priya,Ansari, Monish Arbaz,Shukla, Gaurav,Singh, Maya Shankar
supporting information, p. 5884 - 5888 (2021/11/27)
With unique chemical reactivity, α-oxoketene S,S- and N,S-acetals have attracted enormous attention in the past decades, whereas limited reports exist for their synthesis via eco-compatible protocols. Herein, we developed a one-pot protocol for symmetrical and unsymmetrical α-oxoketene S,S-/N,S-acetals through chemoselective alkylation of α-enolic dithioesters using Mitsunobu chemistry at room temperature. The operationally simple and user-friendly mild protocol tolerates a wide range of alcohols and α-enolic dithioesters/β-ketothioamides. Short reaction time, good yields, highly selective C?S functionalization, and E/Z-stereoselectivity are imperative characteristics of this strategy.
Palladium-Catalyzed Fluoroalkylation via C(sp3)-S Bond Cleavage of Vinylsulfonium Salts
He, Yuan,Huang, Zilong,Ma, Juan,Huang, Fei,Lin, Jie,Wang, Hongmei,Xu, Bao-Hua,Zhou, Yong-Gui,Yu, Zhengkun
supporting information, p. 6110 - 6114 (2021/08/03)
An interrupted Pummerer/palladium-catalyzed fluoro-alkylation strategy was developed for alkenyl C-H fluoroalkylthiolation. Palladium-catalyzed ring-opening fluoroalkylation via aliphatic C-S bond cleavage of the vinylsulfonium salts efficiently afforded
A [5 + 1] annulation strategy for the synthesis of multifunctional biaryls and: P -teraryls from 1,6-Michael acceptor ketene dithioacetals
Althagafi, Ismail,Elagamy, Amr,Kumar, Abhinav,Pratap, Ramendra,Shally,Shaw, Ranjay
, p. 6407 - 6417 (2020/09/07)
A new type of ketene dithioacetal, 2-(3,3-bis-methylsulfanyl-1-arylallylidene)malononitriles containing 1,4 and 1,6-Michael acceptors, were synthesized to study their reactivity for the synthesis of a new molecular entity. We report a [5 + 1] annulation s
Pyrimido-pyrrolopyridazine derivative as well as intermediate, preparation method, pharmaceutical composition and application
-
Paragraph 0086-0090, (2020/02/17)
The invention discloses a pyrimido-pyrrolopyridazine derivative as well as an intermediate, a preparation method, a pharmaceutical composition and application thereof. The preparation method of the pyrimido-pyrrolopyridazine derivative of a formula I shown in the description comprises the following step: in a solvent, under the action of additives, performing a reaction shown in the description onthe compound of a formula IV shown in the description. By adopting the preparation method disclosed by the invention, defects such as multi-step synthesis and low separation yields in a traditional method can be overcome, and various novel heterocyclic compounds with important biological activity can be rapidly synthesized. The pyrimido-pyrrolopyridazine derivative disclosed by the invention hasgood activity of inhibiting production of NO by macrophage RAW264.7.
Transition metal free synthesis of multifunctional thiomethylated-benzenes from aryl/heteroaryl/cyclopropyl methyl ketones
Panwar, Rahul,Althagafi, Ismail,Shally,Shaw, Ranjay,Elagamy, Amr,Shah, Chandan,Yadav, Pratik,Pratap, Ramendra
, (2020/04/28)
A base-promoted strategic synthesis of various functionalized thiomethylated-benzenes has been established from aryl/heteroaryl/cyclopropyl methyl ketone. We can directly access the thiomethylated-benzene nucleus embedded with diverse functional group by
Alternative Palladium-Catalyzed Vinylic C?H Difluoroalkylation of Ketene Dithioacetals Using Bromodifluoroacetate Derivatives
Tian, Shuangquan,Song, Xiaoning,Zhu, Dongsheng,Wang, Mang
supporting information, p. 1414 - 1419 (2018/04/10)
A palladium-catalyzed cross-coupling of α-oxo ketene dithioacetals and bromodifluoroacetate derivatives has been developed for the synthesis of a class of CF2-containing tetra-substituted olefins, which has potential to extend to drug design an
Synthesis of Partially Reduced Imidazo[1,2- a ]pyridines through an Unprecedented Base-Mediated (4+2) Cyclization
Panwar, Rahul,Singh, Surjeet,Yadav, Pratik,Shaw, Ranjay,Kumar, Abhinav,Pratap, Ramendra
, p. 819 - 824 (2017/04/06)
A water-mediated regioselective synthesis of 6,7-diaryl-5-oxo-2,3,5,6-tetrahydroimidazo[1,2-a]pyridine-6-carbonitriles was performed by the reaction of 2-[1-cyano-2,2-bis(methylsulfanyl)vinyl]benzonitrile with 1-aryl-2-(imidazolidin-2-ylidene)ethanones un
