86302-10-5Relevant academic research and scientific papers
"on water" palladium catalyzed diastereoselective boronic acid addition to structurally diverse cyclopropane nitriles
Das, Asish R.,Das, Dwaipayan,Mukherjee, Prasun
, p. 8886 - 8898 (2020/11/23)
An efficient palladium catalyzed diastereoselective addition of arylboronic acids to complex spirocyclopropyl dinitriles is developed in the presence of a catalytic amount of 4-dodecylbenzenesulphonic acid (DBSA) as a Br?nsted acid surfactant in aqueous media. The protocol is also found to be highly effective when different types of nitrile compounds and organo-boron compounds are used. The overall reaction has been found to be very cost efficient since it requires low catalyst loading, mild thermal energy and short reaction time. Wide substrate scope, operational simplicity, good to excellent product yield, and use of green solvents make the reaction a practical route to transform nitrile into a keto functionality in biorelevant heterocyclic scaffolds. The scale-up synthesis of the target scaffolds can also be achieved with ease which also signifies the practicability of this protocol. This journal is
Recycling Catalyst as Reactant: A Sustainable Strategy to Improve Atom Efficiency of Organocatalytic Tandem Reactions
Wei, Wen,Tang, Yuhai,Zhou, Yan,Deng, Ge,Liu, Ziyu,Wu, Jun,Li, Yang,Zhang, Junjie,Xu, Silong
supporting information, p. 6559 - 6563 (2018/10/20)
A sustainable strategy by internally recycling an organocatalyst as a reactant in a downstream reaction to improve the atom efficiency of organocatalytic tandem reactions is described. Specifically, a one-pot tandem Cloke-Wilson/Boulton-Katritzky reaction
Organocatalytic Cloke-Wilson Rearrangement: DABCO-Catalyzed Ring Expansion of Cyclopropyl Ketones to 2,3-Dihydrofurans
Zhang, Jingfang,Tang, Yuhai,Wei, Wen,Wu, Yong,Li, Yang,Zhang, Junjie,Zheng, Yuansuo,Xu, Silong
supporting information, p. 3043 - 3046 (2017/06/23)
An organocatalytic Cloke-Wilson rearrangement of cyclopropyl ketones to 2,3-dihydrofurans is exploited utilizing the homoconjugate addition process. With 1,4-diazabicyclo[2.2.2]octane as the catalyst, the rearrangement in DMSO at 120 °C proceeded in gener
Ru-catalyzed synthesis of dihydrofuroquinolines from azido-cyclopropyl ketones
Yang, Weijun,Xu, Lijun,Chen, Zhengkai,Zhang, Lili,Miao, Maozhong,Ren, Hongjun
, p. 1282 - 1285 (2013/05/09)
An efficient Ru-catalyzed synthesis of dihydrofuroquinolines from azido-cyclopropyl ketones via the reduction-cyclization-rearrangement process is reported. A plausible reaction mechanism for this process is depicted. Additionally, when the reaction was carried out under H2 (1 atm) in the presence of Pd/C, 4-quinolones were obtained in excellent yields.
HOTf mediated cascade reactions of 1-arenoylcyclopropanecarboxylic acids with arenes
Chen, Gen-Qiang,Tang, Xiang-Ying,Shi, Min
supporting information; experimental part, p. 2340 - 2342 (2012/04/18)
The cascade reactions of 1-arenoylcyclopropanecarboxylic acids with arenes proceed smoothly in freshly distilled HOTf to give the corresponding tetrahydro-5H-benzo[c]fluorene derivatives in good yields along with high stereoselectivities under mild conditions. The Royal Society of Chemistry.
CYCLOALKYLATION BY THE α,ω-DIBROMIDES OF COMPOUNDS CONTAINING AN ACTIVATED METHYLENE GROUP AS A METHOD FOR THE SYNTHESIS OF 1,1-DISUBSTITUTED CYCLOALKENES
Zefirov, N. S.,Kuznetsova, T. S.,Kozhushkov, S. I.,Surmina, L. S.,Rashchupkina, Z. A.
, p. 474 - 480 (2007/10/02)
A convenient preparative method was developed for the cycloalkylation of active methylene compounds, including β-diketones, by the dibromides BrCH2(CH2)nCH2Br (n = 0,1,2) in the presence of an excess of potassium carbonate in DMSO.The reaction gives high yields for the dibromides with n = 0 and 2, whereas the formation of cyclobutanes (n=1) is complicated by O,C-alkylation.The 1-substituted 1-acylcyclopropanes undergo thermal isomerization to the corresponding dihydrofuranes.
OPENING OF THE THREE-MEMBERED RING IN 1,1-DISUBSTITUTED CYCLOPROPANES AS A METHOD FOR THE SYNTHESIS OF FUNCTIONAL DERIVATIVES OF PYRAZOLE AND ISOXAZOLE
Zefirov, N. S.,Kozhushkov, S. I.,Kuznetsova, T. S.
, p. 644 - 650 (2007/10/02)
The reaction of 1,1-diacylcyclopropanes with hydrazine and hydroxylamine derivatives, which leads to nucleophilic opening of the three-membered ring and the formation of pyrazole and isoxazole derivatives, was studied.The dependence of the occurrence of t
