Synthesis of 6-alkynylated uridines

1986 ◽  
Vol 64 (8) ◽  
pp. 1560-1563 ◽  
Author(s):  
Hiromichi Tanaka ◽  
Kazuhiro Haraguchi ◽  
Yachiyo Koizumi ◽  
Mariko Fukui ◽  
Tadashi Miyasaka
Keyword(s):  
Coupling Reaction ◽  
Starting Material ◽  
Terminal Alkynes

6-Alkynylated uridines, a hitherto unknown class of compounds, were synthesized by a coupling reaction of terminal alkynes with 6-iodo-2′,3′-O-isopropylidene-5′-O-methoxymethyluridine in the presence of bis(triphenylphosphine)palladium(II) chloride and copper(I) iodide. 6-Ethynyl-2′-deoxyuridine was also prepared by using 6-iodo-3′,5′-O-(tetraisopropyldisiloxan-1,3-diyl)-2′-deoxyuridine as a starting material.

scholarly journals Grignard coupling-based synthesis of vinyl-substituted hydridopolycarbosilane: effect of starting material and polymerization behavior

RSC Advances ◽  
2021 ◽  
Vol 11 (19) ◽  
pp. 11771-11778
Author(s):  
Minji Jeong ◽  
Moon-Gun Choi ◽  
Yoonjoo Lee
Keyword(s):  
Coupling Reaction ◽  
Starting Material ◽  
Polymerization Behavior

Polymerization of VHPCS by the Grignard coupling reaction depended on the type of starting material. In the case of Cl3SiCH2Cl starting material, a stepwise growth manner was shown, due to a coupling between –CH2Cl and the Si–Cl sites.

Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction

2021 ◽  
Vol 43 (1) ◽  
pp. 95-95
Author(s):  
Rifhat Bibi Rifhat Bibi ◽  
Muhammad Yaseen Muhammad Yaseen ◽  
Haseen Ahmad Haseen Ahmad ◽  
Ismat Ullah Khan Ismat Ullah Khan ◽  
Shaista Parveen Shaista Parveen ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Sonogashira Reaction ◽  
Terminal Alkynes ◽  
Vinyl Halides ◽  
Sonogashira Coupling Reaction ◽  
Quinoxaline Derivatives ◽  
Palladium Catalyzed ◽  
High Yields ◽  
Alkyne Derivatives

Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety of important biological potencies. Palladium catalyzed cross coupling process provided an effective synthetic practice for the synthesis of alkyne derivatives of quinoxaline. Vareity of terminal alkynes were coupled with 2-(4-bromophenyl)quinoxaline under optimized conditions for Sonogashira reaction, affording alkyne substituted quinoxaline derivatives in high yields. The optimized reaction conditions for coupling of range of terminal alkyne with quinoxaline basic core render this process significant for designing of medicinally interesting precursors.

Unprecedented one-pot multicomponent synthesis of propargylamines using Amberlyst A-21 supported CuI under solvent-free conditions

RSC Advances ◽  
2015 ◽  
Vol 5 (57) ◽  
pp. 46074-46087 ◽  
Author(s):  
Giovanna Bosica ◽  
John Gabarretta
Keyword(s):  
Coupling Reaction ◽  
Solvent Free ◽  
Environmentally Benign ◽  
Terminal Alkynes ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Solvent Free Conditions

An environmentally benign, one-pot, A3-coupling reaction of various aldehydes, amines and terminal alkynes for the synthesis of propargylamine was catalysed by Amberlyst A-21 supported CuI, under heterogeneous and solvent-free conditions.

Palladium-catalyzed denitrative Sonogashira-type cross-coupling of nitrobenzenes with terminal alkynes

2020 ◽  
Vol 56 (5) ◽  
pp. 790-793 ◽  
Author(s):  
Boya Feng ◽  
Yudong Yang ◽  
Jingsong You
Keyword(s):  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Terminal Alkynes ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

Described herein is a palladium-catalyzed cross-coupling reaction between nitroarenes and terminal alkynes, offering a facile method for C(sp2)–C(sp) bond formation.

Palladium-catalyzed double coupling reaction of terminal alkynes with isocyanides: a direct approach to symmetrical N-aryl dialkynylimines

2020 ◽  
Vol 18 (40) ◽  
pp. 8089-8093
Author(s):  
Zhi-Wei Xi ◽  
Yan He ◽  
Li-Qiu Liu ◽  
Ying-Chun Wang
Keyword(s):  
Coupling Reaction ◽  
Direct Approach ◽  
Quinoline Derivatives ◽  
Terminal Alkynes ◽  
Palladium Catalyzed ◽  
Double Coupling

We have synthesized symmetrical N-aryl dialkynylimines via the palladium-catalyzed double coupling reaction of terminal alkynes with isonitriles, and the obtained dialkynylimines could be readily converted into 2-iodobenzo[f]quinoline derivatives.

Environmentally Benign Microwave-Assisted Sonogashira Preparation of Aromatic Compounds

2011 ◽  
Vol 695 ◽  
pp. 113-116 ◽  
Author(s):  
Suttikiat Puechmongkol ◽  
Boonchoat Paosawatyanyong ◽  
Worawan Bhanthumnavin
Keyword(s):  
Coupling Reaction ◽  
Environmentally Benign ◽  
Conventional Heating ◽  
Microwave Activation ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Mild Conditions ◽  
Aryl Bromides ◽  
Sonogashira Coupling Reaction ◽  
Type Coupling

An efficient Sonogashira-type coupling reaction of terminal alkynes and aryl bromides by microwave activation with short reaction time under mild conditions are presented. It is illustrated herein that the traditional Sonogashira coupling reaction can be achieved with a much more efficient yet environmentally friendly condition. In contrary to the usually required 10 mol% Pd loading and the use of conventional heating at 60 °C for 24 h in order for a reaction to proceed satisfactorily, with a 100 W microwave activation, the reaction of terminal alkynes with substituted aryl bromides can be achieved with only a 2.5 mol% Pd in 10 min. The yield was improved with microwave irradiation.

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