Selective synthesis of (Z)-2-enynyl-2-hydroxy-imidazolidine-4,5-diones via Cu(I)-mediated multicomponent coupling of terminal alkynes, carbodiimides and oxalyl chloride.
نویسندگان
چکیده
(Z)-2-Enynyl-2-hydroxy-imidazolidine-4,5-diones 2 are synthesized for the first time via Cu(I)-mediated (Z)-selective geminal coupling among two molecules of terminal alkynes, carbodiimides, and oxalyl chloride. Further transformation of 2a is performed to yield a highly functionalized spiro heterocyclic compound 5.
منابع مشابه
SBA-15-supported-dithizone-copper(I): An efficient heterogeneous catalyst for synthesis of 1,4-disubstituted 1,2,3-triazoles in water
In this work, the SBA-15-supported dithizone-copper(I) [SBA-15-dtz–Cu(I)] complex as a new heterogeneous catalyst is prepared for the first time. The catalyst prepared is characterized by the FT-IR spectroscopy, SEM, and ICP techniques. This reusable heterogeneous catalyst can be used in the click reactions for the green and facile synthesis of 1,4-disubstituted 1,2,3-triazolesvia a on...
متن کاملSynthesis of novel biologically active heterocyclic compounds from 2-oxo-2H-benzopyran-6-yl-imidazolidine.
6-Aminocoumarin on treatment with oxalyl chloride gives coumarinyl-6-isocynate (1a-c) which on treatment with glycine gives 1H-3-[2'-oxo-2'H-benzopyran-6'-yl]-5-imidazolidine-2, 4-dione (2a-c). (2a-c) when refluxed with o-chlorobenzaldehyde, m-hydroxybenzaldehyde, 3,4-dimethoxybenzaldehyde and 3-nitrobenzaldehyde separately gives 1H-5-(2"-chlorobenzylidene)-3-(2'-oxo-2'H-benzopyran-6'-yl) imida...
متن کاملSynthesis of 1,4-disubstituted 1,2,3-triazoles Catalyzed by Eggshell-supported-Cu(I) Metformin Complex as a Heterogeneous Catalyst in Water
An efficient and eco-friendly method has been developed for the synthesis of 1,4 disubstituted 1,2,3-triazoles using the eggshell-supported-Cu(I) metformin complex as a natural and heterogeneous catalyst. The catalyst prepared is characterized by FT-IR spectroscopy, SEM, and ICP techniques. Terminal alkynes were successfully reacted with alkyl chloride and sodium azide in the presence of CuI im...
متن کاملThree-Component and Click Strategy for Synthesis of β-Hydroxy 1,4-Disubstituted 1,2,3-Triazoles Derivatives Catalyzed by 1,4-Dihydroxyanthraquinone-copper(II) Complex onto Nano AlPO4
In this work, copper(II) heterogeneous nanocatalyst supported on modified AlPO4 (Cu(II)-DA@Nano AlPO4) was used for the synthesis of some biological active heterocyclic molecules, particularly for the efficient conversion of a wide range of non-activated terminal alkynes to β-hydroxy 1,4-disubstituted 1,2,3-triazolethrough a three-component “click” reaction at room temperature in water. The reg...
متن کاملZinc-mediated addition of diethyl bromomalonate to alkynes for the cascade reaction towards polysubstituted pyranones and tetracarbonyl derivatives.
The zinc-mediated regioselective addition reactions of diethyl bromomalonate and aromatic and aliphatic alkynes were investigated for the synthesis of vinyl malonates. When the vinyl organo-zinc intermediates were reacted with acid chlorides 2H-pyran-2-ones were obtained while the application of oxalyl chloride and an amine led to tetracarbonyl derivatives in a one-pot multi-step reaction seque...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 12 21 شماره
صفحات -
تاریخ انتشار 2014