Synthesis of pyridinium ylides and simulation of their 1,3-dipolar cycloaddition mechanism

2017 ◽  
Vol 27 (5) ◽  
pp. 503-505 ◽  
Author(s):  
Maxim R. Radzhabov ◽  
Dmitriy V. Tsyganov ◽  
Tatyana S. Pivina ◽  
Mikhail M. Krayushkin ◽  
Nicolas Seeboth ◽  
...  
Keyword(s):  
Dipolar Cycloaddition ◽  
Pyridinium Ylides

Synthesis of 2-Aminoindolizines by 1,3-Dipolar Cycloaddition of Pyridinium Ylides with Electron-Deficient Ynamides

2015 ◽  
Vol 17 (11) ◽  
pp. 2800-2803 ◽  
Author(s):  
Julien Brioche ◽  
Christophe Meyer ◽  
Janine Cossy
Keyword(s):  
Dipolar Cycloaddition ◽  
Pyridinium Ylides

General and Direct Synthesis of Indolizine-1-carbaldehydes by 1,3-Dipolar Cycloaddition of Phenylpropiolaldehyde with Pyridinium Ylides

2016 ◽  
Vol 2016 (29) ◽  
pp. 4957-4960 ◽  
Author(s):  
Tao Gao ◽  
Xiuling Chen ◽  
Longqiang Jiang ◽  
Minghu Wu ◽  
Haibing Guo ◽  
...  
Keyword(s):  
Direct Synthesis ◽  
Dipolar Cycloaddition ◽  
Pyridinium Ylides

1,3-Dipolar Cycloaddition Reaction of Chromones and Coumarin with Pyridinium Ylides

Heterocycles ◽  
1985 ◽  
Vol 23 (6) ◽  
pp. 1395 ◽  
Author(s):  
Ichiro Yokoe ◽  
Shunsuke Matsumoto ◽  
Yoshiaki Shirataki ◽  
Manki Komatsu
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Pyridinium Ylides

TFA-Mediated DMSO-Participant Sequential Oxidation/1,3-Dipolar Cycloaddition Cascade of Pyridinium Ylides for the Assembly of Indolizines

2019 ◽  
Vol 84 (5) ◽  
pp. 2962-2968 ◽  
Author(s):  
Wen-Ming Shu ◽  
Jian-Xin He ◽  
Xun-Fang Zhang ◽  
Shuai Wang ◽  
An-Xin Wu
Keyword(s):  
Dipolar Cycloaddition ◽  
Pyridinium Ylides

scholarly journals Nucleophilic Dearomatization of Activated Pyridines

Catalysts ◽  
2018 ◽  
Vol 8 (12) ◽  
pp. 632 ◽  
Author(s):  
Giulio Bertuzzi ◽  
Luca Bernardi ◽  
Mariafrancesca Fochi
Keyword(s):  
Nitrogen Heterocycles ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Organometallic Reagents ◽  
Pyridine Nitrogen ◽  
Pyridinium Ylides ◽  
Catalytic Asymmetric ◽  
Synthetic Approaches ◽  
Nitrogen Functionalization ◽  
Pyridinium Ion

Amongst nitrogen heterocycles of different ring sizes and oxidation statuses, dihydropyridines (DHP) occupy a prominent role due to their synthetic versatility and occurrence in medicinally relevant compounds. One of the most straightforward synthetic approaches to polysubstituted DHP derivatives is provided by nucleophilic dearomatization of readily assembled pyridines. In this article, we collect and summarize nucleophilic dearomatization reactions of - pyridines reported in the literature between 2010 and mid-2018, complementing and updating previous reviews published in the early 2010s dedicated to various aspects of pyridine chemistry. Since functionalization of the pyridine nitrogen, rendering a (transient) pyridinium ion, is usually required to render the pyridine nucleus sufficiently electrophilic to suffer the attack of a nucleophile, the material is organized according to the type of N-functionalization. A variety of nucleophilic species (organometallic reagents, enolates, heteroaromatics, umpoled aldehydes) can be productively engaged in pyridine dearomatization reactions, including catalytic asymmetric implementations, providing useful and efficient synthetic platforms to (enantioenriched) DHPs. Conversely, pyridine nitrogen functionalization can also lead to pyridinium ylides. These dipolar species can undergo a variety of dipolar cycloaddition reactions with electron-poor dipolarophiles, affording polycyclic frameworks and embedding a DHP moiety in their structures.

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