scholarly journals Opportunities and challenges for direct C–H functionalization of piperazines

2016 ◽  
Vol 12 ◽  
pp. 702-715 ◽  
Author(s):  
Zhishi Ye ◽  
Kristen E Gettys ◽  
Mingji Dai
Keyword(s):  
Transition Metal ◽  
Small Molecule ◽  
Heterocyclic Compounds ◽  
Structural Diversity ◽  
Synthetic Methods ◽  
Photoredox Catalysis ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Nitrogen Heterocyclic

Piperazine ranks within the top three most utilized N-heterocyclic moieties in FDA-approved small-molecule pharmaceuticals. Herein we summarize the current synthetic methods available to perform C–H functionalization on piperazines in order to lend structural diversity to this privileged drug scaffold. Multiple approaches such as those involving α-lithiation trapping, transition-metal-catalyzed α-C–H functionalizations, and photoredox catalysis are discussed. We also highlight the difficulties experienced when successful methods for α-C–H functionalization of acyclic amines and saturated mono-nitrogen heterocyclic compounds (such as piperidines and pyrrolidines) were applied to piperazine substrates.

Transition metal-catalyzed sp3 C–H activation and intramolecular C–N coupling to construct nitrogen heterocyclic scaffolds

2019 ◽  
Vol 55 (87) ◽  
pp. 13048-13065 ◽  
Author(s):  
Ming Zhang ◽  
Qiuhong Wang ◽  
Yiyuan Peng ◽  
Zhiyuan Chen ◽  
Changfeng Wan ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Transition Metal ◽  
Nitrogen Heterocycles ◽  
Synthetic Organic Chemistry ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Nitrogen Heterocyclic

Nitrogen heterocycles are of great medicinal importance, and the construction of nitrogen heterocyclic scaffolds has been one of the focuses in synthetic organic chemistry.

scholarly journals 3-Acyloxy-1,4-enyne: A new five-carbon synthon for rhodium-catalyzed [5 + 2] cycloadditions

2014 ◽  
Vol 86 (3) ◽  
pp. 409-417 ◽  
Author(s):  
Casi M. Schienebeck ◽  
Xiaoxun Li ◽  
Xing-zhong Shu ◽  
Weiping Tang
Keyword(s):  
Transition Metal ◽  
Optical Purity ◽  
Kinetic Studies ◽  
Synthetic Methods ◽  
High Optical Purity ◽  
Transition Metal Catalyzed ◽  
Propargylic Esters ◽  
Metal Catalyzed ◽  
Pharmaceutical Agents ◽  
Type Of Transition

Abstract Seven-membered rings are ubiquitous in natural products and pharmaceutical agents, and their syntheses continue to stimulate the development of novel synthetic methods. The [5 + 2] cycloaddition is one of the most efficient ways to access seven-membered rings since the two-carbon components (alkenes, alkynes, or allenes) are readily available. Prior to our study, however, there was only one type of transition-metal-catalyzed [5 + 2] cycloaddition: the reaction between vinylcyclopropanes and alkenes, alkynes, or allenes. We recently developed a new type of transition-metal-catalyzed [5 + 2] cycloaddition, where the five-carbon building block is 3-acyloxy-1,4-enyne (ACE). Our recent progress on Rh-catalyzed intra- and intermolecular [5 + 2] cycloadditions of ACEs and alkynes is summarized in this article. Using chiral propargylic esters, bicyclic products were prepared in high optical purity by the intramolecular [5 + 2] cycloadditions. Monocyclic seven-membered rings were synthesized by intermolecular [5 + 2] cycloaddition of ACEs and alkynes. Kinetic studies indicated that the rate of this intermolecular cycloaddition was significantly accelerated when the acetate was replaced by dimethylaminobenzoate. DFT calculations suggested that novel metallacycles were generated by a Rh-promoted oxidative cycloaddition of 1,4-enynes accompanied by a 1,2-acyloxy migration of propargylic esters.

Transition metal-catalyzed reactions in heterocyclic chemistry

2002 ◽  
Vol 74 (8) ◽  
pp. 1327-1337 ◽  
Author(s):  
Irina P. Beletskaya
Keyword(s):  
Transition Metal ◽  
Heterocyclic Compounds ◽  
Heterocyclic Chemistry ◽  
Substitution Reactions ◽  
Multiple Bonds ◽  
Palladium Catalyzed ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

The palladium-catalyzed substitution reactions forming carbon­carbon and carbon­element bonds, as well as nickel-catalyzed addition of E­H and E­E' bonds across multiple bonds, are considered in their application to the chemistry of heterocyclic compounds.

Recent Advances in the Transition Metal Catalyzed Addition of Carboxylic Acids to Alkynes

2021 ◽  
Vol 25 ◽  
Author(s):  
Victorio Cadierno
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Carboxylic Acids ◽  
Heterocyclic Compounds ◽  
Biologically Active ◽  
Recent Advances ◽  
Enol Esters ◽  
Cascade Processes ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

: Recent advances in the metal-catalyzed hydrofunctionalization of alkynes with carboxylic acids are comprehensively reviewed. Both inter- and intramolecular processes, leading respectively to enol esters and lactones, are discussed, as well as the involvement of these transformations in the synthesis of natural products and biologically active molecules, and the assembly of elaborated heterocyclic compounds though cascade processes. Literature published since 2011 is covered.

Transition metal catalyzed meta-C–H functionalization of aromatic compounds

2015 ◽  
Vol 13 (7) ◽  
pp. 1930-1941 ◽  
Author(s):  
Jiong Yang
Keyword(s):  
Transition Metal ◽  
Aromatic Compounds ◽  
Synthetic Methods ◽  
Directing Group ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

This review summarizes synthetic methods for directing group guided, transition metal catalyzed meta-C–H functionalization of aromatic compounds.

Transition metal-catalyzed iodine(iii)-mediated nitrene transfer reactions: efficient tools for challenging syntheses

2017 ◽  
Vol 53 (3) ◽  
pp. 493-508 ◽  
Author(s):  
B. Darses ◽  
R. Rodrigues ◽  
L. Neuville ◽  
M. Mazurais ◽  
P. Dauban
Keyword(s):  
Transition Metal ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Synthetic Methods ◽  
Transfer Reactions ◽  
Nitrene Transfer ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

The main synthetic applications of catalytic C(sp3)–H amination and alkene aziridination reactions are discussed in the context of natural product synthesis. The examples highlight that these synthetic methods now firmly belong in the organic chemist's toolbox.

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