BF3·OEt2-Promoted Intramolecular Nucleophilic Substitution; Synthesis of Dibenzopyranones and Coumarins from Biaryltriazenes

2013 ◽  
Vol 2013 (24) ◽  
pp. 5475-5484 ◽  
Author(s):  
Xiaobo Shang ◽  
Lijun Xu ◽  
Weijun Yang ◽  
Jun Zhou ◽  
Maozhong Miao ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Intramolecular Nucleophilic Substitution

scholarly journals Synthesis of Carbohydrate Based Macrolactones and Their Applications as Receptors for Ion Recognition and Catalysis

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3394
Author(s):  
Surya B. Adhikari ◽  
Anji Chen ◽  
Guijun Wang
Keyword(s):  
Nucleophilic Substitution ◽  
Supramolecular Chemistry ◽  
Copper Sulfate ◽  
Substitution Reaction ◽  
Biological Properties ◽  
Anion Binding ◽  
Nucleophilic Substitution Reaction ◽  
Binding Properties ◽  
Intramolecular Nucleophilic Substitution ◽  
Leaving Groups

Glycomacrolactones exhibit many interesting biological properties, and they are also important in molecular recognitions and for supramolecular chemistry. Therefore, it is important to be able to access glycomacrocycles with different sizes and functionality. A new series of carbohydrate-based macrocycles containing triazole and lactone moieties have been designed and synthesized. The synthesis features an intramolecular nucleophilic substitution reaction for the macrocyclization step. In this article, the effect of some common sulfonate leaving groups is evaluated for macrolactonization. Using tosylate gave good selectivity for monolactonization products with good yields. Fourteen different macrocycles have been synthesized and characterized, of which eleven macrocycles are from cyclization of the C1 to C6 positions of N-acetyl D-glucosamine derivatives and three others from C2 to C6 cyclization of functionalized D-glucosamine derivatives. These novel macrolactones have unique structures and demonstrate interesting anion binding properties, especially for chloride. The macrocycles containing two triazoles form complexes with copper sulfate, and they are effective ligands for copper sulfate mediated azide-alkyne cycloaddition reactions (CuAAC). In addition, several macrocycles show some selectivity for different alkynes.

Stereoselective Formation oftrans-2,5-Disubstituted Tetrahydropyrans by Intramolecular Nucleophilic Substitution and a Computational Study at the AM1 Level

2001 ◽  
Vol 74 (10) ◽  
pp. 1901-1907 ◽  
Author(s):  
Ryukichi Takagi ◽  
Hiroko Nishitani ◽  
Sigeharu Takenami ◽  
Kazumasa Okada ◽  
Satoshi Kojima ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Computational Study ◽  
Intramolecular Nucleophilic Substitution

Pd(OAc)2/SPPh3 accelerated activation of gem-dichloroalkenes for the construction of 3-arylchromones

2015 ◽  
Vol 51 (99) ◽  
pp. 17576-17579 ◽  
Author(s):  
Jianming Liu ◽  
Weiwei Song ◽  
Yuanyuan Yue ◽  
Ren Liu ◽  
Hong Yi ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Intramolecular Nucleophilic Substitution

The Pd-catalyzed regioselective intramolecular nucleophilic substitution of gem-dichloroalkene derivatives with salicylaldehydes leading to the synthesis of 3-arylchromones has been developed.

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