Reverse of Regioselectivity in Intramolecular Nucleophilic Substitution of π-Allyl Palladium Species. Highly Selective Formation of Vinylic Cyclopropanes via the Pd(0)-Catalyzed Coupling−Cyclization Reaction of Organic Iodides with 2-(2‘,3‘-Dienyl)malonates

2000 ◽  
Vol 2 (16) ◽  
pp. 2495-2497 ◽  
Author(s):  
Shengming Ma ◽  
Shimin Zhao
Keyword(s):  
Nucleophilic Substitution ◽  
Cyclization Reaction ◽  
Intramolecular Nucleophilic Substitution ◽  
Selective Formation

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.

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 A Synthesis of 4-Chloro-2-(trichloromethyl)pyrimidines and Their Study in Nucleophilic Substitution

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 530-537 ◽  
Author(s):  
Moisés Romero-Ortega ◽  
Michelle Trujillo-Lagunas ◽  
Ignacio Medina-Mercado ◽  
Ivann Zaragoza-Galicia ◽  
Horacio Olivo
Keyword(s):  
Nucleophilic Substitution ◽  
Intramolecular Cyclization ◽  
Nitrogen Heterocycles ◽  
Cyclization Reaction ◽  
Substitution Reactions ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
Acyl Chlorides ◽  
Nucleophilic Substitution Reactions ◽  
One Pot Synthesis

A convenient two-step, one-pot synthesis of 4-chloro-2-(trichloromethyl)pyrimidines starting from 2-(trichloromethyl)-1,3-diazabutadienes is described. These nitrogen heterocycles were prepared by a sequential acylation/intramolecular cyclization reaction between 2-(trichloromethyl)-1,3-diazabutadienes and acyl chlorides in the presence of triethylamine followed by treatment with POCl3. This is the first report for the synthesis of this type of 4-chloro-2-(trichloromethyl)pyrimidine derivatives and serves as a source for a wide variety of other substituted pyrimidines by nucleophilic substitution reactions.

Facile synthesis of novel 3,4,5-trisubstituted-1,2,4-triazin-6(1H)-onesviaa sequential Ugi–Smiles type/nucleophilic substitution/cyclization reaction

2018 ◽  
Vol 42 (21) ◽  
pp. 17533-17537
Author(s):  
Sorour Ramezanpour ◽  
Mohammad Nasim Rezaei ◽  
Aref Vaezghaemi ◽  
Frank Rominger
Keyword(s):  
Nucleophilic Substitution ◽  
Biological Activities ◽  
Cyclization Reaction ◽  
Facile Synthesis ◽  
Innovative Strategy ◽  
Pyrimidine Bases

An innovative strategy for synthesis of a library of complex multi-substituted 1,2,4-triazine-6-ones. These structures are analogues of pyrimidine bases with possible enhanced biological activities.

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