Domino Sonogashira Coupling/Cyclization Reaction Catalyzed by Copper and ppb Levels of Palladium: A Concise Route to Indoles and Benzo[b]furans

2011 ◽  
Vol 353 (5) ◽  
pp. 713-718 ◽  
Author(s):  
Ruiping Wang ◽  
Song Mo ◽  
Yongzhong Lu ◽  
Zengming Shen
Keyword(s):  
Cyclization Reaction ◽  
Sonogashira Coupling

Palladium complexes with an annellated mesoionic carbene (MIC) ligand: catalytic sequential Sonogashira coupling/cyclization reaction for one-pot synthesis of benzofuran, indole, isocoumarin and isoquinolone derivatives

2020 ◽  
Vol 49 (43) ◽  
pp. 15238-15248
Author(s):  
Akshi Tyagi ◽  
Noor U Din Reshi ◽  
Prosenjit Daw ◽  
Jitendra K. Bera
Keyword(s):  
Palladium Complexes ◽  
Phosphine Ligands ◽  
Cyclization Reaction ◽  
Sonogashira Coupling ◽  
One Pot ◽  
Efficient Catalyst ◽  
One Pot Synthesis

A Pd(ii) complex containing a mesoionic carbene and phosphine ligands is an efficient catalyst for tandem coupling/cyclization reaction.

Probing the Versatility of Shape-Persistent Tetraphenylmethane Dendrimers by Modification of the Skeleton

2019 ◽  
Author(s):  
Julio Ignacio Urzúa ◽  
Sandra Campana ◽  
Massimo Lazzari ◽  
Mercedes Torneiro
Keyword(s):  
Design Principle ◽  
Focal Point ◽  
Sonogashira Coupling ◽  
Terminal Alkyne ◽  
Double Phase ◽  
Rigid Rod ◽  
Convergent Approach ◽  
First And Second Generation ◽  
Oxidative Homocoupling ◽  
Hypercrosslinked Polymers

Tetraphenylmethane has emerged as a recurrent building block for advanced porous materials such as COFs, PAFs and hypercrosslinked polymers. Guided by a similar design principle, we have previously synthesized shape-persistent dendrimers with tetraphenylmethane nodes and ethynylene linkers. Here we report the generality of our approach by describing new dendritic architectures built from tetraphenylmethane. First, we prepared expanded dendrimers where the tetrahedral units are bonded through larger rigid rod spacers. Among the different synthetic strategies tested, the convergent route, with alternating steps of Pd-catalyzed Sonogashira coupling and alkyne activation by removal of TMS masking groups, efficiently afforded the first- and second-generation dendrimers. A second type of compounds having a linear diyne at the core is also described. The dendrimers of generations 1-2 were also synthesized by a convergent approach, with the diyne being assembled in the last step of the synthesis by a Glaser oxidative homocoupling of the corresponding dendrons bearing a terminal alkyne at the focal point. A third-generation dendrimer was also successfully prepared by a double-phase strategy.<br>

Synthesis of Novel Bis-pyrazoles via Electrophilic Cyclization

2019 ◽  
Vol 16 (6) ◽  
pp. 511-516
Author(s):  
Adnan Cetin
Keyword(s):  
13C Nmr ◽  
Cyclization Reaction ◽  
Electrophilic Cyclization ◽  
Pyrazole Derivatives ◽  
Spectral Analyses ◽  
Mass Spectral ◽  
Palladium Catalyzed ◽  
Ft Ir ◽  
Reaction Compound

Efficient steps towards the synthesis of novel (phenyl)(1&#039;-aryl-1,5,5&#039;-triphenyl[3,3&#039;-bi-1Hpyrazol]- 4-yl)methanones 4a-e were developed. The procedure starts from 1-(4-benzoyl-1,5-diphenyl- 1H-3-pyrazolyl)-3-phenyl-2-propyn-1-one (2) which was synthesized by a palladium catalyzed crosscoupling reaction. Compound 2 reacted with various hydrazines to give (E)-(phenyl)[1,5-diphenyl-3- [3-phenyl-1-(2-arylhydrazono)-2-propyn-1-yl]-1H-4-pyrazolyl]methanones E-3a-e. The bis-pyrazole derivatives 4a-e were synthesized from electrophilic cyclization reaction of &#945;,&#946;-acetylenic hydrazones E-3a-e and copper(I) iodide. All synthesized compounds were characterized by FT-IR, 1H, 13C NMR and Mass spectral analyses.

New 2-Alkynyl Derivatives of the Acyclic Nucleoside 9-(2,3-Dihydroxypropyl)adenine and Their 6-Guanidinopurine Counterparts as Potential Effectors of Adenosine Receptors

2003 ◽  
Vol 68 (11) ◽  
pp. 2201-2218 ◽  
Author(s):  
Michal Česnek ◽  
Antonín Holý ◽  
Milena Masojídková
Keyword(s):  
Adenosine Receptors ◽  
Sonogashira Coupling ◽  
Acyclic Nucleoside ◽  
Derivatives Of

A series of the new 2-alkynyl derivatives of the acyclic nucleoside 9-(2,3-dihydroxypropyl)- adenine and their 6-guanidinopurine analogues were prepared by the Sonogashira coupling. The effect of the prepared compounds on A1 and A2A receptors was examined.

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