COPPER-MEDIATED N1-ARYLATION OF BENZOTRIAZOLES

<p>Benzotriazoles are group of bicyclic heterocyclic compounds that contain three nitrogen atoms fused to a benzene ring. Along with their derivatives, they possess a wide range of properties. They are used in medical field, as they exhibit such properties as antibacterial,antiplasmoidal,antiprotozoal, antifungal and anti-inflammatory activities, among others. They are also used in various industries as herbicides, UV absorbers, deicing and antiicing agents and corrosion inhibitors, to list a few. Because of their wide range of applications, we designed a new two-step synthesis for the formation of <em>N-</em>1-aryl benzotriazoles. 1-Hydroxy-1<em>H</em>-benzotriazole <em>N</em>-oxides were synthesized using phenylboronic acid (PhB(OH)₂), pyridine in CH₂Cl₂as the solvent. A wide range of aryl boronic acids showed good reactivity with 1-hydroxy-1<em>H</em>-benzotriazole as well as 6-chloro-1-hydroxy-1<em>H</em>-benzotriazole under established conditions and moderate to high yields of products were isolated. Obtained N-oxides were then deoxygenated using tetrahydroxydiboron (B₂(OH)₄) in MeCN, following previously established conditions. <em>N</em>-Oxides resulting from the reactions of 5,6-dichloro-1<em>H­-</em>hydroxybenzotriazole were difficult to purify and prone to degradation. To alleviate the problem, a two-step one-pot reaction was designed. After <em>N</em>-arylation was complete and without any further purification, the reduction step was performed using B₂(OH)₄in MeCN. The method proved beneficial for the reaction with phenylboronic acid, and no significant improvement was observed in others. A reaction using 2-methoxypyrimidine-4-boronic acid showed that using established conditions, compounds with potential biological activity can be synthesized.</p>

Name thesis:degree_name

Master of Science (M.S.)

Level thesis:degree_level

Thesis

Discipline thesis:degree_discipline

Chemistry

Year dc:date.available

2019

Author dc:creator

• Andrzejewska, Magdalena R

Contributors dc:contributor

• Mahesh K. Lakshman
• Barbara Zajc
• Issa Salame

• Organic Chemistry

Repository record dc:identifier

https://academicworks.cuny.edu/cc_etds_theses/781

OAI identifier oai:identifier

oai:academicworks.cuny.edu:cc_etds_theses-1839